United States v. Christopher Smith

United States Court of Appeals
FOR THE EIGHTH CIRCUIT
___________

No. 07-2956
___________

United States of America, *
*
Plaintiff–Appellee, *
* Appeal from the United States
v. * District Court for the
* District of Minnesota.
Christopher William Smith, *
also known as Chris Jonson, *
also known as Tony Spitalie, *
also known as Robert Jonson *
also known as Bruce Jonson, *
*
Defendant–Appellant. *
___________

Submitted: February 11, 2009
Filed: July 28, 2009
___________

Before LOKEN, Chief Judge, MELLOY and BENTON, Circuit Judges.
___________

MELLOY, Circuit Judge.

This case involves the prosecution of a businessman who sold millions of
dollars of prescription drugs over the Internet without valid prescriptions. A jury
convicted Christopher William Smith of conspiracy to distribute and dispense
controlled substances without an effective prescription in violation of 21 U.S.C. §§
841(a)(1), 841(b)(1)(D), and 846; aiding and abetting the unlawful distribution of
controlled substances in violation of 21 U.S.C. §§ 841(a)(1) and 841 (b)(1)(D), and
18 U.S.C. § 2; aiding and abetting the introduction of misbranded drugs into interstate
commerce in violation of 21 U.S.C. §§ 331(a), 333(a)(2), and 353(b)(1), and 18
U.S.C. § 2; conspiracy to commit money laundering in violation of 18 U.S.C. §
1956(h); and continuing criminal enterprise in violation of 21 U.S.C. § 848(a) and (c).
Applying the U.S. Sentencing Guidelines, the Presentence Investigation Report
(“PSR”) calculated a total offense level of 42, a Category I criminal history, and a
resulting advisory imprisonment range of 360 months to life. The district court
imposed a sentence of 360 months’ imprisonment and five years’ supervised release.

Smith appeals, challenging his convictions for the above-described offenses on
several grounds. He also contests his sentence, arguing that the district court
committed a non-harmless procedural error in violation of Supreme Court’s ruling in
Gall v. United States, 128 S. Ct. 586 (2007), and that his sentence is substantively
unreasonable. We affirm the convictions, vacate the sentence, and remand for
resentencing in light of Gall.

I.

Smith first began selling prescription drugs through Internet websites and spam
emails in 2004. Smith’s business used several different names during its existence,
including Xpress Pharmacy Direct (“Xpress”) and Online Payment Solutions (“OPS”).
After taking an order online, Smith would distribute controlled substances from
abroad to numerous customers throughout the United States. He employed no medical
doctors and sold drugs without prescriptions. When his business began experiencing
shipping problems, however, Smith limited his operations to the United States. Faced
with a stricter regulatory regime, Smith developed an online questionnaire that he
required his customers to complete prior to obtaining prescription drugs through his
sites. The questionnaire required the customer’s name, address, date of birth, phone
number, height, and weight. It allowed customers to select the type of drug that they
wanted to receive and in what quantity. There was also a place on the questionnaire

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for the customer to list a purported medical condition and any medical allergies. No
additional evidence of a purported ailment was required.

Sometime in July 2004, Smith began employing Philip Mach, M.D., to issue
prescriptions to the customers who had filled out the questionnaires posted on Smith’s
sites. In addition to being involved with other online prescription sites, Dr. Mach ran
a traditional medical practice in New Jersey, the only state in which he was licensed
to practice medicine. To receive Dr. Mach’s “prescriptions,” Smith set up a computer
system by which Dr. Mach could log on daily and review the orders that customers
had placed through Smith’s sites. Dr. Mach was therefore never required to examine
these customers face-to-face, review their official medical records, or in any way
verify the limited information and claims that these customers had submitted on the
questionnaires. The system’s default was that all orders would be marked “approved,”
and the evidence at trial established that even in instances where Dr. Mach rejected
a claim, Smith resubmitted the request for additional review (at which time it was
approved). Despite the customers’ lack of interaction with Dr. Mach, each
“prescription” he issued stated that it was provided following a “doctor consultation.”

In addition to the Internet sites, Smith ran call centers both in the United States
and abroad. Customers who wished to place an order for a prescription drug could
call a center, and operators would fill out a form similar to the online questionnaire.
At Smith’s direction, however, the operators employed at the centers also frequently
called prior customers to ask whether they wanted drug refills. Because Smith paid
the operators a commission, the more drugs the operators sold the more money they
made. Testimony established that the entire purpose of the centers was to “sell, sell,
sell.”

Despite allegedly requiring particular information, many of the questionnaires
upon which Dr. Mach issued drugs were lacking in the information necessary for a
physician to issue an appropriate prescription. Some customers requested controlled

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substances that were in no way related to their claimed ailments, yet Dr. Mach
provided “prescriptions” and Smith provided drugs. Some forms lacked basic
identifying information. For example, one questionnaire used an obscene word
instead of a name. Even in that case, however, Dr. Mach provided the “prescription,”
and Smith provided the drugs. At one point, during an investigation of Smith’s
operations, an undercover agent from the Food and Drug Administration (“FDA”)
made three purchases of controlled substances and three purchases of non-controlled
substances through one of Smith’s sites with false information about both his identity
and medical conditions. At no point did Smith or Dr. Mach contact him to verify any
of the information contained on his questionnaires for any of the purchases.

During his work with Smith’s online sites and call centers, Dr. Mach approved
thousands of “prescriptions” per day and was ultimately responsible for issuing over
72,000 orders for pharmaceuticals from July 2004 until mid-2005. The total drug
sales for Smith’s operation at the time it was shut down in May 2005 was over $24
million. The high rate of prescription approval and the resulting income was not
unanticipated, however, as Smith only compensated Dr. Mach for those orders that Dr.
Mach approved. For each “prescription” that Dr. Mach issued, Smith would pay him
$3.50. Smith paid another $3.50 to a middle man from New Jersey, John Guerriero,
who had connected Dr. Mach with Smith. Despite attempts to recruit additional
physicians, Smith was unable to solicit anyone other than Dr. Mach to participate in
his business.

Smith’s online sites were not licensed to distribute controlled substances
directly. As a result, he sought out licensed “brick and mortar” establishments to fill
his orders once Dr. Mach issued a “prescription.” Smith targeted small, independent
pharmacies in numerous states that he believed would become economically
dependent on him and refrain from questioning his business model. Smith attempted
to assuage any fears that the pharmacies raised by assuring them that he was not
dealing in illegitimate Internet prescriptions but that each prescription was a legitimate

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prescription backed by numerous physicians. He claimed that in states where a face-
to-face meeting was required by law, the prescriptions were issued only after
consultation with the customers’ primary-care physicians. Additionally, the contracts
that Smith entered into with these pharmacies stated that his model was FDA
approved and that each “prescription” was issued only after a doctor–patient
consultation. When pharmacies questioned the volume of orders for hydrocodone—a
powerful painkiller sold under brand names such as Vicodin and Norco—Smith would
shift orders to other pharmacies. This shifting occurred several times, as the majority
of the “prescriptions” Dr. Mach issued were for hydrocodone. Smith sold over four-
million tablets of this drug in addition to a much lesser quantity of non-controlled
medication.1 Smith’s business also had a problem with “returned drugs,” or those
drugs that customers could not receive because they were unable to pay for them cash-
on-delivery. Despite the fact that Smith was not authorized to handle controlled
substances and despite the fact that the drugs originally came from traditional brick-
and-mortar pharmacies, the drugs were returned to one of his offices in violation of
federal law.

Around February 2005, the Drug Enforcement Administration (“DEA”) issued
a nationwide directive to pharmacies warning about the legitimacy of online
pharmaceutical operations. The directive explicitly asserted that a questionnaire was
an insufficient method to establish a doctor–patient relationship, as required by federal
statute and regulations. Many of the pharmacies that Smith used to fill Dr. Mach’s
“prescriptions” threatened to quit unless Smith provided them with assurances that his
business model was in compliance with the DEA directive. In response, Smith
arranged to have Dr. Mach and Smith’s attorney send a letter to the pharmacies. The
letter stated that Smith’s business issued valid prescriptions based on legitimate

1
Testimony established that Smith was aware that many, if not all, of his
customers were drug addicts, and he charged high prices for controlled substances
with knowledge that addicts would be willing to pay a premium to satisfy their
addictions.

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doctor–patient relationships. Smith concedes that some of the claims made in the
letter were false.

Throughout Xpress and OPS’s existence, other organizations and businesses,
including boards of pharmacies and the credit-card company, Mastercard, contacted
Smith with concerns about the legality of his operation. As it became clear to Smith
that he was the target of a criminal investigation, he began moving operations to
Canada, along with the laundered proceeds from the drug sales and the personal
property he purchased with those proceeds.

In May 2005, the district court entered a preliminary injunction that shut down
Smith’s online business. The order froze Smith’s bank accounts and assets and further
enjoined Smith from operating any online pharmacy. In violation of that order, Smith
immediately traveled to the Dominican Republic in hopes of setting up another online
site there, and he even developed a plan to flee permanently from the United States
to avoid trial. When he returned to the United States, he was arrested for contempt
and released on bond. Smith was indicted in August 2006 and jailed. Even while in
jail, he continually violated the preliminary injunction by attempting to start a new
online pharmacy and arranging cash transfers. Smith ultimately was transferred to a
maximum-security facility in response to claims that he had threatened to kill a
witness. Smith’s trial began on October 10, 2006, and on November 22, 2006, a jury
found him guilty of the nine counts charged in the Indictment. At various points
during the trial and investigation, several of his coconspirators pleaded guilty to
conspiracy to distribute controlled substances. These coconspirators included Dr.
Mach, a pharmacy recruiter, a business consultant, a computer programmer, and the
person who had served as head of security for Smith’s business.

Smith challenges his convictions on numerous grounds. First, he alleges that
the district court erred in instructing the jury that a prescription’s validity under 21
C.F.R. § 1306.04 is determined by generally accepted medical practices rather than
the specific, regular practice of the issuing doctor. Smith also claims this instruction

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incorporated a civil-liability standard and violated the rule of lenity. Second, Smith
argues that the court erred in instructing the jury that a prescription must be valid in
order to preclude a charge of misbranding under 21 U.S.C. §§ 331(a), 333(a)(2), and
353(b)(1), and that the court’s instruction again violated the rule of lenity. Third,
Smith challenges the court’s failure to exclude certain expert testimony from a
pharmacist, as well as other “prejudicial” testimony. Finally, Smith contends that
insufficient evidence supported his conviction under 21 U.S.C. §§ 841(a)(1),
841(b)(1)(D), and 846. We address each of these claims in turn.

II.

“We review challenges to jury instructions for an abuse of discretion” and “will
affirm if the entire charge to the jury, when read as a whole, fairly and adequately
contains the law applicable to the case.” United States v. Webster, 442 F.3d 1065,
1067 (8th Cir. 2006) (internal quotations omitted). Only where the “instructional error
was prejudicial to the defendant” will we reverse. Id.

A. Definition of “Prescription” Under 21 C.F.R. § 1306.04

Section 841(a)(1) of the Controlled Substances Act (“CSA”) makes it “unlawful
for any person knowingly or intentionally . . . to manufacture, distribute, or dispense
. . . a controlled substance” unless that person is a registered person acting pursuant
to an effective prescription. See 21 U.S.C. §§ 841(a), 822(b); 21 C.F.R. § 1306.04.
Title 21 C.F.R. § 1306.04 describes the conditions under which a registered person
can distribute a controlled substance and requires that, to be “effective,” a
prescription must be “issued for a legitimate medical purpose by an individual
practitioner acting in the usual course of his professional practice.” 21 C.F.R. §
1306.04 (emphasis added); see 21 U.S.C. § 802(21) (defining “practitioner” as a
person who is “licensed, registered, or otherwise permitted . . . to distribute [or]
dispense . . . a controlled substance in the course of professional practice” (emphasis
added)). Lay persons who conspire with or aid and abet a practitioner’s unlawful

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distribution of drugs can be convicted under the CSA and its regulations. See, e.g.,
United States v. Hicks, 529 F.2d 841, 844 (5th Cir. 1976) (security guard); United
States v. Green, 511 F.2d 1062, 1070–71 (7th Cir. 1975) (pharmacy owner). The CSA
also reaches the distribution of controlled substances over the Internet. United States
v. Fuchs, 467 F.3d 889, 896 (5th Cir. 2006); United States v. Nelson, 383 F.3d 1227,
1228–29 (10th Cir. 2004).

Smith was convicted of conspiracy to distribute controlled substances and
aiding and abetting the distribution of controlled substances without an effective
prescription. The instruction the district court provided the jury largely tracked the
language of § 1306.04. The instruction provided:

The [Act] is not violated if a person distributes or dispenses controlled
substances pursuant to a lawful prescription issued for a legitimate
medical purpose [] by an individual practitioner acting in the usual
course of his or her professional practice . . . .

The court further defined “usual course of professional practice” as requiring

that the practitioner [have] acted in accordance with a standard of
medical practice generally recognized and accepted in the United States.
In issuing prescriptions, practitioners are not free to disregard prevailing
standards of treatment.

Smith contends that the instruction was improper because the court’s definition of
“usual course of professional practice” ignored the subjective element embodied in
§ 1306.04’s use of the term “his,” thus contravening the plain language of the
regulation. He argues that “his professional practice” is to be judged with reference
to the particular practices of the issuing doctor, as opposed to generally accepted
medical practices. Because the prescriptions that Dr. Mach issued over the Internet
were “the very heart” of Dr. Mach’s regular medical practice, Smith argues that Dr.
Mach’s actions cannot support Smith’s conspiracy or aiding-and-abetting convictions.

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Smith also argues that to the extent the regulation is ambiguous, the rule of lenity
resolves the issue in his favor. We disagree with Smith’s creative argument.

While we have never before had occasion to address explicitly whether “his
professional practice” under § 1306.04 is to be measured according to a generally
accepted standard of treatment or the practice of a particular doctor,2 the Supreme
Court’s decision in United States v. Moore, 423 U.S. 122 (1975), and the approaches
of our sister circuits are instructive. In Moore, the Supreme Court impliedly approved
a jury instruction that allowed a jury to find a doctor guilty of violating § 841(a) if the
doctor dispensed methadone “other than in good faith for detoxification in the usual
course of a professional practice and in accordance with a standard of medical practice
generally recognized and accepted in the United States.” Id. at 139. The Court’s
statements thus counsel against finding that professional practice is to be measured
according to the practice of a particular doctor and indicate that the appropriate
measure of what constitutes “his professional practice” is an objective one.

2
We have upheld jury instructions in cases involving convictions under § 841(a) and
§ 1306.04 where the instruction provided that a prescription must be issued in the
“usual course of his professional practice” without any discussion of the potential
subjectivity embodied in “his.” See United States v. Katz, 445 F.3d 1023 (8th Cir.
2006); United States v. Plesons, 560 F.2d 890, 897 n.6 (8th Cir. 1977) (“If this doctor
was . . . acting as a doctor in the course of his professional practice, then there’s no
violation. However, if he was not acting in good faith as a doctor, but simply pushing
pills . . . , then he does not come within the exception, and the law is violated.”
(quotation omitted)); United States v. Kershman, 555 F.2d 198, 201 (8th Cir. 1977)
(“[T]he jury was instructed that if the pharmacist believed in good faith that a
prescription was issued and prescribed for a legitimate medical purpose by a physician
acting in the usual accord of his profession, then the pharmacist is excepted from
criminal responsibility.”).

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 Furthermore, the circuit courts to consider a conviction under § 841(a) have
applied a general-practice standard when determining whether the practitioner acted
in the “usual course of professional practice.” See, e.g., United States v. Merrill, 513
F.3d 1293, 1306 (11th Cir. 2008) (“The appropriate focus is not on the subjective
intent of the doctor, but rather it rests upon whether the physician prescribes medicine
in accordance with a standard of medical practice generally recognized and accepted
in the United States.” (quotation omitted)); United States v. Feingold, 454 F.3d 1001,
1011 n.3 (9th Cir. 2006) (“The term ‘professional practice’ implies at least that there
exists a reputable group of people in the medical profession who agree that a given
approach to prescribing controlled substances is consistent with legitimate medical
treatment.”); United States v. Norris, 780 F.2d 1207, 1209 (5th Cir. 1986) (relying on
Moore, 423 U.S. at 139, in dismissing the defendant’s argument that “his” requires
that the government prove that the doctor prescribed drugs for a purpose contrary to
the doctor’s own standards of medical practice because “[o]ne person’s treatment
methods do not alone constitute a medical practice”); cf. United States v. Hurwitz,
459 F.3d 463, 478, 480 (4th Cir. 2006) (“[A]llowing criminal liability to turn on
whether the defendant-doctor complied with his own idiosyncratic view of proper
medical practices is inconsistent with the Supreme Court’s decision in Moore. . . .
Because the instruction proffered by Hurwitz set forth a subjective standard for
measuring his good faith, the instruction was not a correct statement of the law.”);
United States v. Vamos, 797 F.2d 1146, 1153 (2d Cir. 1986) (“To permit a
practitioner to substitute his or her views of what is good medical practice for
standards generally recognized and accepted in the United States would be to weaken
the enforcement of our drug laws in a critical area.”).

Smith’s argument is further undermined by the regulations use of “professional
practice.” 8 C.F.R. § 1306.04. Even assuming that “his professional practice”
requires us to consider Dr. Mach’s individualized practice, that practice must still
comport with the tenants of medical professionalism. In line with the Supreme
Court’s decision in Moore, in United States v. Katz, 445 F.3d 1023 (8th Cir. 2006),

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we indicated that prescriptions issued “outside the bounds of professional medical
practice” include instances where a doctor issues prescriptions “for the purpose of
assisting another in the maintenance of drug habit or . . . for other than a legitimate
medical purpose, i.e.[,] the personal profit of the physician.” Katz, 445 F.3d 1023,
1028 (8th Cir. 2006) (quotation omitted). We are thus not at liberty to eliminate the
requirement that an issuing practitioner’s practice be objectively “professional,” even
assuming that we are required by the regulation to consider “his” particular practice.
See generally Moore, 423 U.S. at 140–43; cf. United States v. Boettjer, 569 F.2d
1078, 1081 (9th Cir. 1978) (indicating that Moore “suggests that the ‘usual course’
standard itself imports considerations of medical legitimacy and accepted medical
standards.”).

Thus informed by the Supreme Court and other controlling and persuasive
precedent, we believe that it was not improper to measure the “usual course of
professional practice” under § 841(a)(1) and § 1306.04 with reference to generally
recognized and accepted medical practices and not a doctor’s self-defined particular
practice. If Smith’s argument that § 1306.04’s use of the word “his” establishes a
subjective standard were to prevail, it would allow an individual doctor to define the
parameters of his or her practice and effectively shield the practitioner from criminal
liability despite the fact that the practitioner may be acting as nothing more than a
“large-scale ‘pusher.’” Moore, 423 U.S. at 143 (finding criminal liability when a
practitioner ceases to act as a physician and instead acts as a drug pusher). This
cannot be the law.

Smith also argues that the definition of “usual course of professional practice”
in Jury Instruction 30 improperly conflated the standard for criminal liability with the
standard for medical malpractice and that he was criminally convicted of breaching
a civil standard of care. We also find this argument unavailing. While Instruction 30
may have incorporated the standard of care often referenced in medical-malpractice
claims, see Boettjer, 569 F.2d at 1081, looking at the jury instructions on the whole,

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we do not believe that the district court suggested that a breach of a civil standard
alone was sufficient to sustain a criminal conviction. See Kershman, 555 F.2d at 201
(“It is axiomatic that the jury instructions should be construed as a whole.”). We are
thus confident that Smith’s conviction rested on the appropriate criminal standard and
not on the lesser, civil one.

It is true that courts have recognized a danger in confusing medical-malpractice
and § 841 standards. See United States v. McIver, 470 F.3d 550, 558 (4th Cir. 2006);
Feingold, 454 F.3d at 1010. In this case, however, even assuming that the use of the
civil standard of care as a definitional tool was improper, the jury instructions on the
whole required more than a finding that Dr. Mach did not adhere to generally accepted
medical standards. The instructions indicated that the Government bore the burden
to prove that Smith distributed or dispensed controlled substances “other than . . . for
a legitimate medical purpose and in the usual course of professional practice.” Thus,
the jury was unable to convict Smith unless it found a failure to adhere to prevailing
medical standards and a lack of legitimate medical purpose. This dual showing is one
that exceeds that required to establish medical malpractice, which focuses largely on
the former finding and may or may not include consideration of the latter. Cf. McIver,
470 F.3d at 559.3

Additional indicators that the instructions did not conflate civil and criminal
standards include the fact that the court explicitly instructed that the standard of proof
applicable in this case was “beyond a reasonable doubt.” See Katz, 445 F.3d at 1032
(rejecting a claim that the burden of proof was lowered because the court “instructed

3
We also note that the statute and regulations make distribution unlawful unless
there is an “effective prescription.” See 21 U.S.C. §§ 841(a), 822(b); 21 C.F.R. §
1306.04. A prescription is only effective if it was both issued in the “usual course of
professional practice” and for a “legitimate medical purpose.” In other words, under
the terms of the statute, the jury is able to convict if either is not met. Arguably, then,
the instruction the court provided the jury was more favorable to Smith than that
required by law.

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the jury that they must find beyond a reasonable doubt that [the doctor] wrote
prescriptions outside the scope of medical practice and not for a legitimate medical
purpose”); Vamos, 797 F.2d at 1153 (“The suggestion that an objective
reasonableness standard exposes a physician to criminal responsibility for nothing
more than the equivalent of malpractice ignores the fact that in a criminal prosecution
the physician may be found guilty only upon proof beyond a reasonable doubt that he
acted outside the scope of medical practice . . . .”). The court also allowed Smith the
possibility of a good-faith defense,4 which is unavailable in malpractice cases. “The
inclusion of a good faith instruction is therefore a plainspoken method of explaining
to the jury a critical difference between the two standards.” McIver, 470 F.3d at
558–60 (indicating courts must “exercise care in setting out the governing standard”

4
Instruction 64 stated, in part:

A person who works with or for a pharmacy or a physician
may not be convicted when he or she distributes or
dispenses controlled substances in good faith for a
legitimate medical purpose and in the ususal course of
professional practice. . . .

....

A controlled substance is distributed or dispensed by
a physician or pharmacist in the usual course of his or her
professional practice and, therefore, lawfully, if the
substance is distributed or dispensed by him or her in good
faith in medically treating a patient.

When you consider the good faith defense, it is the
defendant’s belief that is important. It is the sincerity of his
belief that determines if he acted in good faith.

If the defendant’s belief is unreasonable, you may
consider that in determining his sincerity of belief, but an
unreasonable belief sincerely held is good faith.

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in a § 841 prosecution but approving language setting forth the civil standard when
the court made clear that the Government had to prove its case “beyond a reasonable
doubt,” instructed the jury that the “critical issue . . . was not whether the defendants
had acted negligently,” and included a good-faith instruction (quotation omitted));
Feingold, 454 F.3d at 1011 n.3; United States v. Alerre, 430 F.3d 681, 692 (4th Cir.
2005) (“The trial court was careful to spell out the differences between the criminal
standard and the civil standard. Indeed, it . . . emphasized that [the defendants] could
not be convicted if they had dispensed the controlled substances at issue ‘in good
faith.’”). In conclusion, we find that the jury instructions, taken as a whole, precluded
a conviction based on the civil standard of liability.

B. “Prescription” Under 21 U.S.C. §§ 331(a), 333(a)(2), 353(b)(1)

Title 21 U.S.C. § 331(a) of the Food, Drug, and Cosmetic Act (“FDCA”)
prohibits introducing a “misbranded” drug into interstate commerce. A drug is
“misbranded” unless dispensed upon a “prescription of a practitioner licensed by law
to administer such drug.” 21 U.S.C. § 353(b)(1)(C). Smith contends that the district
court erred when it instructed the jury that Smith must have dispensed the drugs
pursuant to a “valid” prescription to avoid conviction under the statute. He contends
that the prescription need not be “valid” to avoid a misbranding charge because
validity is not required by the plain language of the statute. Smith further argues that
even if a valid prescription were required, the district court provided an incorrect
definition of what constitutes “valid.” The challenged jury instruction stated:

A “prescription” [under the Act] and in these instructions means only a
valid prescription. A valid prescription means one issued in the usual
course of professional practice and for a legitimate medical purpose, as
explained earlier in the Instructions.

Despite the fact that § 353(b) does not explicitly state that a prescription must
be valid, we find unpersuasive Smith’s argument that any order for a controlled
substance issued by someone authorized to issue prescriptions will preclude a

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misbranding conviction. The text of the statute provides limited clarity as to the
parameters of “prescription,” as it is not explicitly defined. See United States v.
Whiting, 165 F.3d 631, 633 (8th Cir. 1999) (“The starting point . . . is always the
language of the statute itself.”). And “[a]bsent a specific statutory definition, words
used in a statute should be given their common meaning.” Levings v. Califano, 604
F.2d 591, 593 (8th Cir. 1979) (citing Banks v. Chi. Grain Trimmers Ass’n, 390 U.S.
459, 465 (1968)).

To determine whether the prescription must be valid to preclude Smith’s
conviction, we find helpful a case in the U.S. District Court for the Southern District
of Florida. See United States v. Nazir, 211 F. Supp. 2d. 1372 (S.D. Fla. 2002). Nazir
addressed the meaning of “prescription” under § 353(b) by surveying various sources
for the “ordinary meaning and usage” of the word, and the court ultimately determined
that the validity of the prescription was of legal import. Id. at 1375. After discussing
the definition of “prescription” in three different sources, including a medical textbook
published around the time Congress enacted § 353(b), the court concluded that

the word prescription in § 353(b)(1), in common parlance, means only
a bona fide order—i.e., directions for the preparation and administration
of a medicine, remedy, or drug for a real patient who actually needs it
after some sort of examination or consultation by a licensed doctor—
and does not include pieces of paper by which physicians are directing
the issuance of a medicine, remedy, or drug to patients who do not need
it, persons they have never met, or individuals who do not exist.

Id. In affirming the district court’s conclusion, the Eleventh Circuit described §
353(b)(1) as “deeming a prescription drug misbranded if it is dispensed other than
pursuant to a valid prescription,” United States v. Munoz, 430 F.3d 1357, 1366 (11th
Cir. 2005) (emphasis added), and we agree.

In addition to the common meaning of the word, interpretive case law is also
helpful in defining “prescription” under the statute. Cf. Gellman v. United States,

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235 F.2d 87, 93 (8th Cir. 1956) (“Where words are susceptible of several meanings,
the court is at liberty to determine from the legislative history and surrounding
circumstances the sense in which the words were used in a statute.”). While this court
has not addressed the meaning of “prescription” under § 353(b) directly, in White v.
United States, 399 F.2d 813, 817–18 (8th Cir. 1968), we impliedly approved the Fifth
Circuit’s conclusion that an invalid prescription is not a prescription within the
meaning of § 353(b) at all. See Brown v. United States, 250 F.2d 745 (5th Cir. 1958).
In Brown, a physician sold controlled substances to two undercover federal agents
without having “given them any prescription, . . . physically examined either of them,
. . . questioned them[,] or . . . otherwise attempted to acquaint himself with either the
physical condition or needs of either man.” Id. at 745. A jury convicted the physician
of violating § 353(b)(1). Id. The Fifth Circuit found no error in a jury instruction that
indicated that the existence of “a bona fide [doctor–patient] relationship . . . bears on
the question whether there had ever been a ‘prescription’” under the provision. Id. at
747. The court then affirmed the conviction, upholding the jury’s finding that the
doctor had “dispensed the tablets without prescription.” Id.

In White, while addressing a conviction under a different statutory provision,
we discussed favorably the Fifth Circuit’s ultimate conclusion in Brown. White, 399
F.2d 817–18. In White, a doctor had frequently provided controlled substances to
numerous people, including an undercover agent. Id. at 815–16. This was despite the
fact that the doctor had asked “no questions concerning the state of [the recipients’]
health.” Id. A jury convicted the doctor under then-existing provisions of the FDCA
that prohibited “the sale, delivery or other disposition of a drug” except by certain
persons “acting in the ordinary and authorized course of his business, profession,
occupation, or employment.” 21 U.S.C. §§ 331(q)(2), 360a(b) (1968), amended by
21 U.S.C. § 801 (1970). Persons authorized to distribute drugs under the provision
included “[p]ractitioners licensed by law to prescribe” such drugs “while acting in the
course of their professional practice.” Id. § 360a(a)(4) (1965), amended by 21 U.S.C.
§ 801 (1970). We affirmed the conviction, highlighting and agreeing with various

-16-
courts’ reasoning under numerous provisions of the FDCA that “as a prerequisite to
the issuance of a prescription . . . a bona fide physician–patient relationship must
exist.” White, 399 F.2d at 816–18; see also Webb v. United States, 249 U.S. 96,
99–100 (1919) (holding under the Harrison Act that when a doctor provided morphine
to a habitual user “for the purpose of providing the user[] with morphine sufficient to
keep him comfortable by maintaining his customary use” there was not a “physician’s
prescription,” and that “to call such an order for the use of morphine a physician’s
prescription would be so plain a perversion of meaning that no discussion of the
subject [was] required”).

Besides contravening the common meaning of “prescription” and contradicting
persuasive authority, not requiring a “valid” prescription would undermine the
FDCA’s purpose by allowing practitioners to write fraudulent prescriptions (or
prescriptions that otherwise contravened the law) and escape criminal liability for such
acts. Treating a prescription as a piece of paper divorced from its context—i.e., with
no analysis as to whether it is valid—would, in effect, exempt licensed practitioners
from prosecution under the misbranding statute all together. See Kordel v. United
States, 335 U.S. 345, 349 (1948) (“[T]here is no canon against using common sense
in reading a criminal law, so that strained and technical constructions do not defeat its
purpose by creating exceptions from or loopholes in it.”). The purpose of
misbranding laws is to protect the public from potentially dangerous drugs. See
Brown, 250 F.2d at 747 (“The Supreme Court has on several occasions held that the
purpose of the legislation is the protection of the people from dangerous products . .
. .” (citing United States v. Dotterweich, 320 U.S. 277 (1943); United States v.
Sullivan, 332 U.S. 689 (1948)); see also Nazir, 211 F. Supp. 2d. at 1375–76
(concluding that the statute should not be interpreted to render the expressed need for
physician supervision a nullity). And we refuse to construe the statute in a way that
would significantly undermine that purpose.

We further conclude that the district court did not err in defining a “valid
prescription” as one issued in the “usual course of professional practice and for a

-17-
legitimate medical purpose,” distinguishing between the two and requiring a finding
of both. First, it was proper to require that the prescription be for a “legitimate
medical purpose.” See Webb, 249 U.S. at 99–100. Second, as established above, a
valid prescription requires a bona fide physician–patient relationship. Whether a
prescription was issued in the “usual course of professional practice” required that the
jury inquire into whether Dr. Mach adhered to prevailing medical standards when
issuing his prescriptions. Many of the factors that establish the existence of a
physician–patient relationship and thus a valid prescription under the statute—such
as whether Dr. Mach considered the actual needs of the patient, the quantity of the
drug he prescribed, the type of drugs he prescribed and for what purpose, and the
extent to which he supervised the issuance of the drug—are considerations necessarily
included in a determination as to whether or not a prescription was issued in
accordance with generally accepted practices. See Brown, 250 F.2d at 747 n.2.

C. Rule of Lenity

The rule of lenity fails to save Smith’s arguments that the challenged jury
instructions were erroneous. The rule requires that “ambiguity concerning the ambit
of criminal statutes should be resolved in favor of lenity.” Cleveland v. United States,
531 U.S. 12, 25 (2000) (quotation omitted). The rule, however, should not be invoked
if ambiguity can be otherwise resolved. United States v. Kowal, 527 F.3d 741, 747
(8th Cir.), cert. denied, 129 S. Ct. 612 (2008). Given that the CSA’s and FDCA’s
structure and language resolve any ambiguities contained within “his professional
practice” or “prescription,” as outlined above, “the rule of lenity is not implicated
here.” Id.

III.

Smith also challenges the district court’s failure to exclude certain expert
testimony and other allegedly prejudicial evidence. “We review the district court’s
evidentiary rulings for abuse of discretion.” Katz, 445 F.3d at 1031 (quotation
omitted). “Even where we find that the district court has abused its discretion with

-18-
respect to an evidentiary ruling, we will not reverse the conviction if the error was
harmless.” United States v. Lupino, 301 F.3d 642, 645 (8th Cir. 2002).

A. Expert Testimony

The Government offered expert testimony from Dr. Carmen Catizone, a
pharmacist. Smith argues that Catizone’s testimony exceeded the scope of his
expertise when he testified about the standard of care to which a doctor must adhere
in order to prescribe properly a controlled substance. More specifically, Smith
challenges the admissibility of Catizone’s testimony regarding the type of medical
practice that satisfies 21 C.F.R. § 1306.04 and Catizone’s conclusion that there was
insufficient information about Dr. Mach’s alleged patients for a physician to have
issued valid prescriptions. Smith additionally objects to Catizone’s testimony as to
the meaning of the text of § 1306.04. Upon review of the trial transcript, we reject
Smith’s argument.

“Federal Rule of Evidence 702 permits a district court to allow the testimony
of a witness whose knowledge, skill, training, experience, or education will assist a
trier of fact in understanding the evidence or to determine a fact in issue.” United
States v. Kirkie, 261 F.3d 761, 765 (8th Cir. 2001) (citing Fed. R. Evid. 702). We
have previously admitted “testimony tying standards of care to the existence of a
legitimate medical purpose to write a prescription.” Katz, 445 F.3d at 1032.

Despite the fact that Catizone was not a medical doctor, we find that his
testimony regarding the type of information a doctor should have to prescribe a
particular drug, and whether Dr. Mach met that standard, fell within his expertise.
Catizone is a certified pharmacist and has been the executive director of the National
Association of Boards of Pharmacy (“NABP”) for twenty years. The NABP drafts
model laws regulating pharmaceuticals, which necessitates that Catizone be
particularly familiar with both the CSA and the FDCA. Furthermore, Caitzone
annually gives testimony before Congress, state legislatures, and state committees on

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Internet pharmacies and the relevant laws. Through his work with the NABP,
Catizone also helped institute a national accreditation program that developed
standards of operation for legitimate Internet pharmacies in conjunction with the FDA
and the DEA, among other agencies and organizations. Under that program, to
maintain certification, pharmacies must comply with both state and federal law, which
includes filling only legitimate prescriptions and refusing to fill those that appear
suspect. See 21 C.F.R. § 1306.04(a) (providing that pharmacists are required by law
to determine whether a prescription has been issued in the usual course of professional
practice and for a legitimate medical purpose or be subject to criminal liability).

As a result, Catizone’s job requires a working knowledge of what constitutes
a valid prescription, and this cannot be divorced from having an awareness as to the
quantity and quality of patient information a doctor must have in order to prescribe
a particular drug. See United States v. Jones, 570 F.2d 765, 769 (8th Cir. 1978) (“Dr.
Burton testified that before prescribing any drug, a physician must take a medical
history and make some physical examination. Witness Burton possesses a Ph.D. in
pharmacology. Although not an M.D., his twenty years of teaching at the Washington
University Medical School qualifies him as an expert entitled to express an opinion
as to medical procedures in prescribing drugs . . . .”); see also United States v. Bek,
493 F.3d 790, 797 (7th Cir.), cert. denied, 128 S. Ct. 549 (2007) (noting “expert
testimony from a pharmacist who explained that [the doctor’s] practices were
dangerous and very unusual” and that the doctor “should have conducted several
diagnostic tests and reviewed patients’ medical histories before prescribing drugs such
as Vicodin”).

Catizone has also helped the Government identify over 1,500 “rogue
pharmacies,” or pharmacies that operate in contravention of state and federal law and
offer medications to patients or customers without legitimate or valid prescriptions.
In fact, Smith concedes that Catizone is an expert in identifying rogue pharmacies.
Factors that Catizone uses to make a determination of whether a pharmacy is rogue
under the NABP standards include the type of medical information the site requests

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and whether it requires face-to-face interaction. In order to properly identify a rogue
pharmacy, then, Catizone must pass judgment on the substance of a patient–doctor
interaction. Again, to make this determination it is important that Catizone have in-
depth knowledge regarding what is needed for a medical doctor to issue a legitimate
prescription under prevailing practice, and it is apparent from his testimony that he
did.

We do not doubt that there may be instances in which a pharmacist is not
qualified to provide expert testimony on the standard of care necessary to prescribe
a particular drug. Given Catizone’s background and extensive involvement with
identifying rogue pharmacies, however, the district court’s refusal to exclude this
testimony does not constitute an abuse of discretion. Catizone thus properly testified
within his expertise as to the type of relationship usually considered necessary for a
doctor to issue a valid prescription.

Furthermore, while we find Catizone’s testimony about the legal meaning of §
1306.04 troubling, we conclude that it was harmless and does not merit remand. As
mentioned, Catizone is required to be familiar with state and federal laws and has
frequently testified before Congress and legislatures; however, he is not qualified to
interpret the text of the statutes and regulations in open court. Thus, we agree with
Smith that, at several points, Catizone exceeded his qualifications as an expert:

Q. I am showing you a copy of 21 CFR 1306.04. Are you familiar with
this law?

A. Yes.

Q. What do the phrases, included in this law, “usual course of
professional practice” and “legitimate medical purpose” mean?

....

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 [A.] Based upon my knowledge of state laws and also the Controlled
Substances Act, this refers to the scope of practice that a physician may
engage in and also responsibility for that physician to follow all of the
laws and requirements as indicated in federal and state law.

....
Q. You’ll notice that I have circled the word “his” in this particular
regulation. Why is that included in 1306.04?
Well, where it indicates “his professional practice,” does that
mean we are dealing with a subjective standard of professional practice?

[A.] No. What we’re dealing with here is a discretion that’s provided
to the physician to operate within their practice, but the physician must
still follow all of the laws governing that practice.

Moreover, it is “the judge and not a witness” that “is to instruct the fact finder on the
applicable principles of law.” Hogan v. Am. Tel. & Tel. Co., 812 F.2d 409, 411 (8th
Cir. 1987) (per curiam) (citing Marx & Co., Inc. v. Diners’ Club Inc., 550 F.2d 505,
509–10 (2d Cir. 1977) (“It is not for witnesses to instruct the jury as to applicable
principles of law, but for the judge. . . . The special legal knowledge of the judge
makes the witness’ testimony superfluous.”)).

This error alone does not necessarily warrant reversal. Here, Catizone’s
testimony, although beyond his expertise, stated the correct formulation of the law.
More importantly, the district court ultimately instructed as to the correct legal
standard under § 1306.04 at the close of the evidence. Absent harm, the district
court’s evidentiary ruling provides no grounds for relief with regard to Catizone’s
expert testimony. See Fed. R. Crim. P. 52(a).

B. Prejudicial Evidence

Smith also argues that the district court erred in failing to exclude various
unduly prejudicial and irrelevant statements of a Government cooperating witness.
The witness testified that Smith had sent him to Prague to solicit prostitutes on

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Smith’s behalf and that Smith and the witness intended to become “international
pimps.” The Government argues that the evidence of solicitation was admissible to
head-off a co-defendant’s attempt to impeach the Government witness’s credibility
under Federal Rule of Evidence 608 and also as non-character evidence admissible to
show Smith’s intent to commit his substantive offenses under Federal Rule of
Evidence 404(b). The Government alternatively claims that Smith’s co-defendant
“opened the door” to the evidence by raising it on cross-examination and that there
can be no reversible error. See United States v. Beason, 220 F.3d 964, 968 (8th Cir.
2000) (“It is fundamental that where the defendant ‘opened the door’ and ‘invited
error’ there can be no reversible error.” (quotation omitted)).

Assuming without deciding that the challenged evidence was inadmissible
impeachment evidence and inadmissible non-character evidence, and assuming
without deciding that a co-defendant’s testimony that is prejudicial to another co-
defendant does not open the door to the evidence, we find that any such error was
harmless beyond a reasonable doubt. See Fed. R. Crim. P. 52(a) (providing that an
error in the admission of evidence only provides a basis of relief if the error affected
the defendant’s “substantial rights”).

Although Smith argues that the testimony made Smith “look like a lowlife with
a criminal character,” which “clearly stuck with the jury” and formed the basis of the
conviction, we must view the error in light of the evidentiary record as a whole. This
analysis includes “the overall strength of the prosecution’s case.” United States v.
Honken, 541 F.3d 1146, 1160 (8th Cir. 2008) (quotation omitted); United States v.
No Neck, 472 F.3d 1048, 1054 (8th Cir. 2007) (indicating that the proper question is
whether “the guilty verdict actually rendered in this trial was surely unattributable to
the error” (quoting Sullivan v. Louisiana, 508 U.S. 275, 279 (1993) (emphasis
omitted))). In view of the extensive testimony and documentary evidence that the
Government presented detailing Smith’s operation of the rogue pharmacy during more
than twenty days of trial, discussed infra, the evidence of Smith’s guilt is
overwhelming. Having carefully reviewed the record, we conclude that any

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evidentiary error did not affect Smith’s substantial rights and was harmless. See
United States v. McCauley, 601 F.2d 336, 339 (8th Cir. 1979) (finding that the
admission of a recording that contained “vulgarity, racial slurs, and cavalier
statements concerning past [bad acts]. . . . was harmless [error] given the
overwhelming evidence of [the defendant’s] guilt of the crime charged”).

In addition to evidence of Smith’s attempted solicitation, Smith also contends
that the district court abused its discretion by allowing testimonial evidence
concerning a wrongful death suit filed against Smith’s business. The suit alleged that
a drug addict had ordered drugs from Smith’s business and subsequently committed
suicide. The witness testified that Smith was unconcerned by the suit and had laughed
upon learning of the death. Smith objected to the testimony. After sustaining the
objection, the court issued a curative instruction telling the jury to disregard evidence
of the death because there was no link between OPS and the suicide. The court also
issued a similar instruction prior to submitting the case to the jury for deliberation.

“The admission of allegedly prejudicial testimony is ordinarily cured by an
instruction to the jury to disregard the testimony.” United States v. Nelson, 984 F.2d
894, 897 (8th Cir. 1993). It is our role, however, to “determine with fair assurance
whether, in spite of the instruction, the verdict was substantially swayed by the error.”
Id. (quotation omitted). When considering the “prejudicial effect of any allegedly
improper testimony,” we look to “the trial context of the error[] and the prejudice
created thereby as juxtaposed against the strength of the evidence of the [defendant’s]
guilt.” Id. “This court will affirm a conviction, despite the introduction of an
inadvertent prejudicial comment, where there was ‘substantial evidence’ of guilt.”
United States v. Urick, 431 F.3d 300, 304 (8th Cir. 2005). While the testimony here
concerning the wrongful-death suit was improper, the court immediately issued a
curative instruction to the jury and further informed the jury that it was to disregard
the evidence of the suicide at the close of the case, even absent such a request from
Smith. See Nelson, 984 F.2d at 897 (noting how “aggressively” the district court

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acted to cure the error). Furthermore, as discussed infra, the evidence as to Smith’s
guilt was overwhelming. See id. We thus conclude again that the district court
committed no reversible evidentiary error.

IV.

“This court reviews the sufficiency of the evidence de novo, viewing the
evidence in the light most favorable to the government, with all reasonable inferences
and credibility determinations made in support of the jury’s verdict.” Katz, 445 F.3d
at 1028 (quotation omitted). Smith argues that there was insufficient evidence for a
reasonable jury to determine that Dr. Mach issued prescriptions outside of the “usual
course of his professional practice” and thus for this court to sustain his conspiracy
and aiding and abetting convictions under § 841(a). We disagree.

“A prosecution under § 841 requires proof beyond a reasonable doubt that the
doctor was acting outside the bounds of professional medical practice, as his authority
to prescribe controlled substances was being used not for treatment of a patient, but
for the purpose of assisting another in the maintenance of a drug habit or of dispensing
controlled substances for other than a legitimate medical purpose, i.e. the personal
profit of the physician.” Id. at 1028 (internal quotation omitted). Sufficient evidence
supports the jury’s conclusion that Dr. Mach was acting outside the ordinary course
of professional practice when he issued the prescriptions upon which Smith’s
conviction was based.

Perhaps the most probative evidence that Dr. Mach was prescribing drugs to
“assist[] another in the maintenance of a drug habit or . . . for other than a legitimate
medical purpose,” id., is that Dr. Mach himself explicitly so stated. In addition to this
admission, Dr. Mach further testified about his traditional medical practice and his
prescription policy prior to working with online pharmacies. That policy required
face-to-face consultations so that Dr. Mach was able to obtain what he considered the
information necessary to prescribe an appropriate drug in an appropriate quantity. Dr.

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Mach explained that his work with the online pharmacy differed from his office
practice because “[t]here was never an established doctor/patient relationship. There
was never a face-to-face examination. There was never a history. There was no
physical examination. There was no legitimate prescription written and signed and the
prescriptions were not valid.” See United States v. Hayes, 595 F.2d 258, 261 (5th Cir.
1979) (upholding conviction of a pharmacist where the doctor testified “that any
prescriptions written by [the doctor] were not written in the usual course of medical
practice or for legitimate medical purpose”). To the extent the Smith’s challenge to
the sufficiency of the evidence asks us to review the jury’s conclusion that Dr. Mach
was credible, we decline. Not only are “[q]uestions involving the credibility of
witnesses . . . for the jury to resolve,” but Dr. Mach’s testimony was corroborated by
additional documentary and testimonial evidence. United States v. Lop Bounmy, 403
F.3d 1018, 1021 (8th Cir. 2005) (“[T]he uncorroborated testimony of an accomplice
is sufficient to sustain a conviction if it is not otherwise incredible or unsubstantial on
its face.” (quotation omitted)).

Additional evidence supporting Smith’s conviction includes testimony that Dr.
Mach never physically examined or even met with those who were the recipients of
the controlled substances before writing over 72,000 prescriptions. The evidence
further indicates that Dr. Mach approved each order submitted to him, despite the fact
that, in at least one instance, the name on the prescription was an obscene word and
not a person. Dr. Mach placed no limit on the type of drugs that he would prescribe,
allowed customers to choose the type and brand of drug that they desired for their
self-stated alleged medical conditions, provided no limitations on the quantity of drugs
that customers could obtain at one time or within a particular time period, and did not
monitor dosage in any way. See, e.g., Moore, 423 U.S. at 142–43; Katz, 445 F.3d at
1026–28 (affirming a conviction where there was testimony that the doctor received
no medical history, rarely performed physical exams, and provided month-long
prescriptions every two weeks); see also United States v. Paskon, No. 4:07-CV-1161
(CEJ), 2008 WL 2039233, at *5 (E.D. Mo. May 12, 2008) (collecting cases “regarding
the scope of ‘professional practice’ . . . in the context of criminal prosecutions of

-26-
physicians under 21 U.S.C. § 841”). The fact that Dr. Mach was paid per order
approved also supports a finding that his prescriptions were for other than a legitimate
medical purpose but rather for his “personal profit.” Katz, 445 F.3d at 1028.

Catizone’s testimony regarding the applicable standard of care further supports
Smith’s conviction. As discussed above, Catizone testified within his expertise as to
whether or not Dr. Mach issued prescriptions in accordance with generally prevailing
medical standards. He identified several factors pointing to the conclusion that the
online pharmacy through which Dr. Mach issued those prescriptions was not
legitimate and that the prescriptions were thus invalid. Such indicators included the
fact that the questionnaires often failed to list the customer’s ailment, the reason for
the prescription, and other relevant information about the patient’s medications and/or
allergies. Additionally, Catizone testified that the prescriptions that Dr. Mach issued
were for excessive quantities of drugs relative to the medical condition the
prescription was allegedly treating. Dr. Mach also at times prescribed a drug that was
not intended or appropriate to treat the claimed ailment. Catizone further questioned
Dr. Mach’s ability to approve the 72,000 prescriptions at issue, at times, over 1,000
in a single day, given that the “medical literature has reported that the average time
it takes for a physician . . . to conduct a medication or patient profile . . . is . . .
between twelve and twenty minutes.” He further pointed out the disproportionately
high percentage of controlled substances that Dr. Mach prescribed relative to
prescriptions for non-controlled substances used to treat illnesses or diseases such as
diabetes and high blood pressure.

In conclusion, viewing the evidence in a light most favorable to the
Government, we consider it sufficient to support the jury’s conclusion that Dr. Mach
issued the prescriptions outside the ordinary course of professional practice and
without legitimate medical purpose. Smith’s conviction must stand.

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 V.

Finally, Smith argues that the district court committed a procedural sentencing
error when it required that Smith show extraordinary circumstances to merit a
downward variance. Smith also argues that his sentence of 360 months’ imprisonment
was substantively unreasonable. Because we find reversible procedural error, we do
not address Smith’s substantive-reasonableness argument.
A. Standard of Review

Reviewing a sentence, this court must “first ensure that the district court
committed no significant procedural error, such as failing to calculate (or improperly
calculating) the Guidelines range, treating the Guidelines as mandatory, failing to
consider the § 3553(a) factors, selecting a sentence based on clearly erroneous facts,
or failing to adequately explain the chosen sentence—including an explanation for any
deviation from the Guidelines range.” Gall v. United States, 128 S. Ct. 586, 597
(2007). “If the decision was procedurally sound, we then review the substantive
reasonableness of the sentence under the abuse-of-discretion standard considering the
totality of the circumstances.” United States v. Alvizo-Trujillo, 521 F.3d 1015, 1017
(8th Cir. 2008).

If the defendant properly preserves a procedural error, our review is for
harmless error. United States v. Henson, 550 F.3d 739, 741 (8th Cir. 2008), cert.
denied, 129 S. Ct. 2736 (2009). “This circuit requires more than a request for a non-
guidelines sentence in order to preserve . . . Gall error; the defendant must object to
the district court’s erroneous application of the law.” United States v. Bain, 537 F.3d
876, 881 (8th Cir. 2008), vacated and remanded on other grounds, 129 S. Ct. 2157
(2009). If a party fails to object in the district court, we review a procedural
sentencing error for plain error. See United States v. Burnette, 518 F.3d 942, 946 (8th
Cir. 2008).

The Government asserts that Smith failed to preserve his objection to the
court’s treatment of his request for a downward variance and that our review is one

-28-
of plain error. We disagree. While failing to use the word “object,” Smith engaged
in a lengthy dialogue with the district court about the Eighth Circuit’s “draconian” and
“unreasonable” precedent in relation to the district court’s ability to grant a variance.
Smith also discussed the fact that the Supreme Court had granted certiorari in United
States v. Gall, 446 F.3d 884 (8th Cir. 2006), rev’d 128 S. Ct. 586 (2007), to address
what he characterized as “unreasonable” precedent. Finally, he further emphasized
that the Supreme Court’s determination that the Guidelines are “truly advisory” must
govern.

Contrary to the Government’s claim, Smith’s statements were beyond a simple
request for a non-Guidelines sentence and amount to more than mere commentary
about the perceived unfairness of the law. Cf. Bain, 537 F.3d at 881 (applying plain-
error review when the defendant “inform[ed] the judge of the course of action he
wished the judge to take”—i.e., receive a non-Guidelines sentence—and “stat[ed] the
exact sentence sought”); Alvizo-Trujillo, 521 F.3d at 1018 (reviewing for plain error
where the statement to be construed as an objection “was merely commentary” about
the Guidelines range being “unreasonably high” and “was made before the district
court announced the improper presumption and the sentence”); Burnette, 518 F.3d at
946–47 (“After withdrawing his objections to the PSR, [the defendant] made no
further objections to his sentence.”). Given Smith’s statements and their context, we
find that he preserved the error for appeal. See United States v. Pirani, 406 F.3d 543,
549 (8th Cir. 2005) (en banc) (“To preserve an error . . . , an objection must be timely
and must clearly state the grounds for the objection.” (internal quotation and alteration
omitted)). We therefore review for harmless error.

B. Procedural Error in Sentencing

The district court sentenced Smith to 360 months’ imprisonment in August
2007, four months prior to the Supreme Court’s decision in Gall. Before Gall, “[o]ur
cases required that the justification for a variance be proportional to the extent of the
difference between the advisory range and the sentence imposed.” United States v.

-29-
Marron-Garcia, 555 F.3d 1040, 1041 (8th Cir. 2009) (quotation omitted). “One
formulation [of this proportionality review] asked whether an ‘extraordinary variance’
was supported by ‘comparably extraordinary circumstances.’” Id. (quoting United
States v. Claiborne, 439 F.3d 479, 481 (8th Cir. 2006), vacated as moot, 551 U.S. 87
(2007)). In Gall, the Supreme Court “held that an appellate standard requiring
‘proportional’ justifications for variances from the guideline range was inconsistent”
with Supreme Court precedent. United States v. Lee, 553 F.3d 598, 601 (8th Cir.
2009) (quoting Gall, 128 S. Ct. at 594). But the Court also “found it ‘uncontroversial
that a major departure should be supported by a more significant justification than a
minor one.’” Id. at 601–02 (quoting Gall, 128 S. Ct. at 597).

We have several times stated that “[u]nder this court’s pre-Gall legal
framework, district courts had less discretion to make a major variance than they now
enjoy [post-Gall], but [that] they had ample discretion to make a minor variance.”
Marron-Garcia, 555 F.3d 1040, 1041 (internal citation and quotation omitted); see also
Lee, 553 F.3d at 602 (“[T]he pre-Gall legal framework gave district courts less
discretion to make a major variance than they now enjoy.”). The current state of the
law stems from the fact that while Gall made clear that we may no longer require
“‘extraordinary’ circumstances to justify a sentence outside the Guidelines range,” this
court’s rule had not been to “require extraordinary circumstances to justify every
non-guideline sentence.” Marron-Garcia, 555 F.3d at 1041 (quotation omitted).

Smith claims that given the state of the law at the time of his sentencing, and
the lack of clarity concerning the amount of discretion district-court judges possessed
to make major variances, the district court did not fully realize the extent of its
discretion to impose a below-Guidelines sentence. As a result, Smith claims that the
district court should have the opportunity to reconsider the sentence in light of Gall.

During the sentencing phase of his trial, Smith argued for a downward variance
from 360 months to life to the statutory minimum of 240 months. His argument was
based on numerous grounds, including the potential sentencing disparities with other

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online-pharmacy cases. In making his motion, he emphasized that the court was
empowered to grant the variance in its discretion. But the court refused, stating:

[Y]ou know what the circuit does for every variance that a judge does for
a departure downwards, it essentially reverses. . . . I placed somebody on
probation and home detention and they said, No, you can’t do that
variance . . . . And so . . . it’s clear, coming from our circuit, they don’t
even want to see any type of variance downwards unless it can be so
agreed to, almost, by the Government (emphasis added).

Addressing the potential-sentencing-disparity argument specifically, the court
responded that it had “been reversed a number of times dealing with variances and
departures . . . based on the issue of similar[ly situated defendants].” The court further
stated that even “if there’s a variance that’s going to be granted, it can’t be to 20 years
because from 360 to 240, that’s automatic reversal.” We agree with Smith that these
comments raise questions about whether the district court doubted that, as a practical
matter in our circuit pre-Gall, it possessed the discretion to vary significantly to the
requested statutory minimum. And, as a result, we find that the district court
committed procedural error.

Furthermore, we do not find the error harmless. “The government bears the
burden of proving the district court’s error was harmless and must show that no grave
doubt exists as to whether the error substantially influenced the outcome of the
proceedings.” United States v. Greene, 513 F.3d 904, 908 (8th Cir. 2008) (quotation
omitted). While the court showed disdain for Smith’s actions and believed that he was
eligible for a lengthy sentence based, in part, on his own aggravating conduct, the
record also indicates that the court found “some merit” in “the sentencing position of
the defendant” but, out of caution, would not vary due to the belief that pre-Gall it
would result in “automatic reversal.” Taking the court’s comments highlighted above
in light of the proportionality-focused circuit law at the time, along with the statement
that it would “follow the Eighth Circuit precedent dealing with how to sentence an
individual,” we are unsure whether the court would have given Smith the same

-31-
sentence absent an understanding that it was effectively not permitted to vary to the
degree that Smith requested. See United States v. Cullen, 432 F.3d 903, 906 (8th Cir.
2006) (“[W]e cannot say with any confidence that the district court would not have
sentenced the defendant to a lesser sentence . . . . Because [the defendant] was
sentenced at the bottom of the Guidelines range, we are left with grave doubt as to
whether the error was harmless, and we remand for resentencing.” (quotations
omitted)).

As the dissent aptly states, we recognize that the sentencing judge’s Statement
of Reasons is a “critical part of the sentencing record,” and we acknowledge the
comprehensive nature of the district court’s statements here. We do not believe,
however, that the district court’s statements that it had “power to grant a variance from
the Guideline range” and that a “sentence within the Guideline range is reasonable”
undercuts a finding of procedural error in this case. Nor do we believe that these
statements differ from the statements the district court made during sentencing. Both
the sentencing transcript and the Statement of Reasons indicate that the district court
believed that it could vary. The sentencing transcript also indicates, however, that the
district court believed that its power to do so was constrained by then-Eighth Circuit
precedent and nothing in the Statement of Reasons contradicts that. Given the court’s
statements and the context of Smith’s sentencing, we are not convinced that the
district court’s statement that it knew it had the power to vary necessitates a
conclusion that the district court was confident in the level of discretion it had to grant
a departure of the magnitude that Smith requested upon the justifications that Smith
presented.5

5
The dissent cites United States v. Garcia, 236 F. App’x 225, 226 (8th Cir.
2007) (per curiam) (unpublished), as evidence that the district court could not have
“mistakenly believed” that it “lacked discretion to vary downward to the statutory
minimum.” In Garcia, the same sentencing judge granted a twenty-month variance
to a below-Guidelines range sentence. Garcia, 236 F. App’x at 226. But, again, a
grant of a twenty-month variance does not necessarily require a finding in this case
that the court believed it had discretion to grant a major variance to a statutory
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 Contrary to the dissent’s contention, our finding of procedural error is not
intended to, in any way, burden the sentencing judge. Given the district court’s
comments during sentencing, it is clear that the court was frustrated by what it
perceived as this court’s overly rigorous review of sentencing decisions, as well as his
personal experience with sentencing reversals. (The former being a perception
confirmed by the Supreme Court in Gall.) While the dissent cites statistics indicating
the frequency with which District of Minnesota judges granted downward variances
and also highlights cases where we upheld pre-Gall, below-Guidelines downward
variances, what matters in determining the mind set within which the district court
was operating when it sentenced Smith is not the actuality of whether judges varied
generally or whether those cases in which this specific judge varied were reversed on
appeal. Rather, what matters is the district court’s perception of the Eighth Circuit’s
response to its actions.

In sum, the district court indicated that Smith’s claim for a variance had “some
merit,”6 but it generally seemed to have felt constrained by Eighth Circuit practice.

minimum without requiring extraordinary circumstances. In fact, in Garcia, the court
rejected the defendant’s motion for a variance to the statutory minimum, which would
have been a sixty-eight month variance. Id. Garcia, then, does not eliminate our
concern that while the district court believed that it had discretion to vary, it
erroneously (and understandably, given the state of the law) questioned whether the
reasons to make such a major variance had to be extraordinary. Additionally, as the
dissent indicates, we acknowledge that the district court’s comments about “automatic
reversal” were made in the context of “cases in which he varied downward from a
prison sentence to a non-prison sentence.” Again, however, this supports rather than
undercuts the argument that the district court may not have believed it possessed the
discretion to make a major variance such as the one Smith requested. By referencing
such cases, the district court appeared to be analogizing a variance from 360 months
to 240 months to a prison to non-prison sentence.
6
One may argue that the refusal to grant even a small variance makes any
discussion of a more substantial variance essentially moot. However, the district
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Rather than insulting the judge, then, we believe that remanding the case to allow the
district court to re-sentence Smith in the first instance after Gall provides the district
court with the due deference it deserves to perform its charge with the guidance of
clearer precedent. It may be, in fact, that the district court finds that the sentence it
originally imposed upon Smith was appropriate, but we prefer to give the district court
the chance to exercise that sentencing discretion now that more clarity exists as to its
discretion and the level of scrutiny this court will impose. See United States v.
Feemster, No. 06-2059, slip op. at 8–9 (8th Cir. July 13, 2009) (en banc).

Accordingly, we vacate Smith’s sentence and remand for resentencing.

VI.

Having considered all of the issues raised by the defendant on appeal, we affirm
the judgment of conviction. We vacate the sentence, however, and remand in light of
Gall.

LOKEN, Chief Judge, concurring in part and dissenting in part.

I join Parts I-IV of the court’s opinion. But I dissent from Part V, which
misrepresents the sentencing record and ignores relevant prior decisions in contriving
a supposed procedure error that imposes unnecessary burdens on a busy, careful and
experienced sentencing judge, Chief Judge Michael J. Davis of the United States
District Court for the District of Minnesota.

1. Some ten years ago, at the urging of the Sentencing Commission, the
Judicial Conference Criminal Law Committee reminded district judges that the

court’s comment about the motion having “some merit” makes us reluctant to resolve
the variance issue on that basis. Moreover, as stated before, we feel the district court
is in the best position to determine, in the first instance, what it meant by that
comment and what it would have done under the more deferential Gall standard.
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Statement of Reasons portion of the judiciary’s Judgment in a Criminal Case form
should be completed as part of every sentence. Compliance, which had been rather
lax, is now nearly universal. The Statement of Reasons is a critical part of the
sentencing record. It not only helps the Commission gather accurate sentencing data,
it also gives the sentencing judge a chance to reflect on the sentence and to
supplement, or even supplant, impromptu comments at the sentencing hearing that
may have been incomplete or inaccurate. Here, Chief Judge Davis included a thirty-
two-page Statement of Reasons in the Judgment five days after Smith’s hearing.
Findings relating to ten enhancements took up twenty-two pages. After determining
the advisory guidelines range, and reciting the advisory nature of the Guidelines7 and
the sentencing factors in 18 U.S.C. § 3553(a), the Statement of Reasons explained:

Although the Court acknowledges its power to grant a variance
from the Guideline range, the Court concludes that a sentence within the
Guideline range is reasonable. Smith was a drug kingpin who received
great financial gain from his illegal activities while consciously
disregarding the risk of death or serious bodily injury to the addicts,
upon whose addictions his profits were based. . . . Smith plotted to kill
a Government witness and attempted to continue his fraudulent scheme
in three different countries . . . . Smith has demonstrated that he does not
obey Court orders and that, in the absence of a serious Guideline
sentence, he is likely to reoffend . . . .

Although the Court has concluded that a Guideline sentence is
reasonable in this case, a sentence at the low end of the Guideline range
is sufficient . . . .

(Emphasis added.) Part V pays lip service to Chief Judge Davis’s Statement of
Reasons but refuses to believe it.

7
The court also described the Guidelines as “advisory” at the sentencing
hearing, before stating that it “will not vary.”
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 2. Prior to the sentencing hearing, Smith filed a memorandum urging Chief
Judge Davis to grant a variance down to the mandatory minimum sentence of 240
months in prison. As Part V notes, in denying Smith the ten-year downward variance
he requested, Chief Judge Davis commented, “if there’s a variance that’s going to be
granted, it can’t be to 20 years because . . . from 360 to 240, that’s automatic
reversal.” The comment reflected our pre-Gall cases requiring that an extraordinary
variance be justified by extraordinary circumstances, a formulation rejected in Gall.
128 S. Ct. at 595. However, as Part V acknowledges, the Supreme Court in Gall
reaffirmed the proportionality principle when it stated, “We find it uncontroversial
that a major departure should be supported by a more significant justification than a
minor one,” id. at 597. Putting aside the hyperbolic reference to “automatic reversal,”
and focusing on the Statement of Reasons, there was no procedural error in denying
the variance Smith requested because Gall did not change the fact that, as Chief Judge
Davis determined, Smith requested a “major departure” but presented no “significant
justification.”

3. The Sentencing Commission’s “Sourcebook of Federal Sentencing
Statistics” for the three fiscal years prior to Smith’s sentencing reveal that District of
Minnesota judges granted downward judicial variances in 22%, 21%, and 15% of their
post-Booker cases, ranking seventh, eighth, and fifteenth out of the ninety-four federal
district courts in that category. See Table 26 in the 2005, 2006, and 2007
Sourcebooks. Less than two months before Smith’s sentencing, and six months before
the Supreme Court decided Gall, we affirmed Chief Judge Davis’s grant of a variance
twenty months below the bottom of the advisory guidelines range, rejecting
defendant’s argument that Chief Judge Davis mistakenly believed he lacked discretion
to vary downward to the statutory minimum. United States v. Garcia, 236 F. App’x
225, 225-26 (8th Cir. 2007) (unpublished). Three months before Garcia, we affirmed
another sentence in which Chief Judge Davis varied downward, rejecting the
argument that he committed procedural error by treating the Guidelines as mandatory.
United States v. Lynch, 477 F.3d 993, 998 (8th Cir. 2007).

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 Part V emphasizes Chief Judge Davis’s comments at sentencing expressing
frustration at being reversed “a number of times” for granting downward variances.
But Chief Judge Davis expressly stated he was speaking “hypothetically,” and the
comments referred to cases in which he varied downward from a prison sentence to
a non-prison sentence, cases presenting the same type of variance later upheld in Gall.
See United States v. Miller, 484 F.3d 964, 965-67 (8th Cir. 2007), vacated and
remanded, 128 S. Ct. 871 (2008); United States v. Gayekpar, 211 F. App’x 533, 535-
36 (8th Cir. 2007) (unpublished). In December 2006, we affirmed Judge Magnuson’s
grant of a variance from eighteen months in prison to five years’ probation in a high-
profile case, which demonstrated to District of Minnesota judges that even downward
variances to non-prison sentences were not automatically reversed. United States v.
Wadena, 470 F.3d 735, 736-37, 740 (8th Cir. 2006). Particularly in light of the
Statement of Reasons, Chief Judge Davis’s comments do not suggest a belief that he
had no authority to grant a substantial variance to Smith.

The sentencing record in this case is a far cry from the sentencing records in the
cases on which Part V relies, such as United States v. Greene, 513 F.3d 904, 907 (8th
Cir. 2008). Here, the entire sentencing record, including particularly the elaborate
Statement of Reasons, leaves me with complete confidence that Chief Judge Davis
would not have granted Smith a downward variance had the sentence been imposed
a few months after, instead of a few months before, the Supreme Court’s decision in
Gall. As the sentence was imposed without procedural error and is reasonable, it
should be affirmed. Accordingly, I respectfully dissent from Part V.
______________________________

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