United States v. Macedo, Gregorio

In the
United States Court of Appeals
For the Seventh Circuit
____________

Nos. 02-3563, 02-3564 & 02-3842
UNITED STATES OF AMERICA,
Plaintiff-Appellee, Cross-Appellant,
v.
GREGORIO MACEDO,
Defendant-Appellant,
and

VICTOR HUGO CONTRERAS,
Defendant-Appellant, Cross-Appellee.

____________
Appeals from the United States District Court for
the Northern District of Illinois, Eastern Division.
No. 01 CR 57—David H. Coar, Judge.
____________
ARGUED OCTOBER 22, 2003—DECIDED APRIL 14, 2005
____________

Before FLAUM, Chief Judge, and EASTERBROOK and
WILLIAMS, Circuit Judges.
WILLIAMS, Circuit Judge. Gregorio Macedo and Victor
Hugo Contreras were convicted of various drug offenses.
Defendant Macedo alleges several violations of Apprendi v.
New Jersey, 530 U.S. 466 (2000), which he contends render
his convictions and sentence infirm. He also argues that the
2 Nos. 02-3563, 02-3564 & 02-3842

government lacked sufficient evidence to support his
convictions. Defendant Contreras argues that evidence of
prior bad acts was improperly admitted in violation of
Rule 404(b) of the Federal Rules of Evidence. The govern-
ment also appeals the district court’s decision to grant
defendant Contreras a one point downward departure based
on his alien status. We affirm both convictions. However,
because we find that the district court erred in its decision
to downward depart, we must remand defendant Contreras
for resentencing. In addition, in response to Macedo’s
petition for rehearing, we vacate his sentence as well and
remand his case for resentencing consistent with the Supreme
Court’s recent decision in United States v. Booker, 125 S. Ct.
738 (2005).

I. THE TRIAL
The following facts were presented at trial. On January
20, 2001, Francisco Maldonado Herrera (Maldonado) and
Ricardo Mendez, Mexican nationals, traveled from Morelia,
Mexico to O’Hare International Airport in Chicago, Illinois
with over 400 grams of methamphetamine in the soles of
their shoes. Months prior to their trip, Maldonado and
Mendez were both approached in Mexico by a man known
only as “Rene” and asked if they were willing to serve as
drug carriers to the United States for $1500 per trip. Rene
told the men that once in the United States, they would be
met by a man named “Hugo” at the airport who would
exchange the shoes containing the methamphetamine for
new ones and purchase each a return ticket to Mexico.1

1
While this was Mendez’s first smuggling trip to the United States,
it was Maldonado’s third. On the two prior occasions, however,
Maldonado traveled alone. His first trip occurred on November 3,
2000. Upon arrival at O’Hare, Maldonado was met by “Hugo,”
(continued...)
Nos. 02-3563, 02-3564 & 02-3842 3

Maldonado was stopped by United States Customs
Inspector Carlos Torres who noticed that he was wearing
brand-new shoes which appeared too large for his feet. After
receiving several evasive responses to his inquiries, Inspec-
tor Torres asked to see Maldonado’s shoes, where he found
the methamphetamine. Maldonado agreed to cooperate with
the government by wearing a wire to record conversations
between the defendants and Mendez. He also agreed to call
Mexico in an effort to locate Contreras and Macedo in
Chicago.2 Maldonado was able to reach an associate of
Rene’s who gave him Contreras’s cellular phone number as
well as Macedo’s home telephone number. Maldonado then
phoned Contreras who agreed to meet him in the airport. All
of these phone conversations were recorded by government
officials.
While Mendez made it through customs, his contact,
“Hugo,” was not at the airport to meet him. During his wait,
he made several phone calls to Mexico attempting to locate
his contact. He was able to reach family members in Mexico
who gave him two phone numbers as contacts. His family
members received the information from Rene. The numbers
were later identified as Gregorio Macedo’s home telephone
number and cellular phone number.
After several tries, Mendez was able to make contact with
the defendants who met him at a diner near O’Hare

1
(...continued)
whom he later identified in court as Victor Hugo Contreras.
Contreras and Maldonado drove from the airport to Contreras’s
home where they exchanged the drug shoes for new ones. The men
then returned to the airport and Contreras purchased Maldonado’s
return ticket to Mexico. This scheme occurred once more on
November 17, 2000. Maldonado’s testimony was corroborated by
the Customs Record Log, which showed that he previously entered
O’Hare Airport on November 3, 2000, and November 17, 2000.
2
Both defendants were residing illegally in the United States.
4 Nos. 02-3563, 02-3564 & 02-3842

Airport. The three men then drove to a shoe store where
Macedo purchased a replacement pair of shoes for Mendez’s
return. After the trip to the shoe store, the three men
checked into a motel near the airport. According to Mendez,
the motel bill was also paid for by Macedo. The shoes con-
taining the methamphetamine were left in the motel room
and after receiving Maldonado’s call, they returned to the
airport. The four men met in Terminal 5 and began dis-
cussing Maldonado’s experience with the customs agent.
This conversation was recorded. Shortly thereafter, all four
men were arrested by authorities.
Following the arrest, the government recovered the shoes
from the motel room which contained 436.9 grams of meth-
amphetamine (found to be 91% pure with an approximate
street value of $175,000). The shoes seized from Maldonado
at the airport contained 441.9 grams of methamphetamine
(also 91% pure with a parallel street value). After a search
of Contreras’s car, the government also found the key to the
motel room rented by Macedo in the glove compartment.
Mendez and Maldonado pleaded guilty and agreed to
testify against Macedo and Contreras at trial. In addition
to the testimony previously discussed, the evidence admitted
during trial included: the testimony of the two cocon-
spirators, various customs agents, a Drug Enforcement
Agent, and several police officers; the shoes seized at the
airport and the motel room containing methamphetamine;
transcripts of recorded conversations between conspiracy
participants in Mexico and Maldonado; the phone numbers
communicated to Maldonado and Mendez; the defendants’
cellular and home phone records; and the motel room key
recovered from defendant Contreras’s vehicle.
During the trial, the district court also allowed Officer
Daniel Vasquez to testify concerning two earlier encounters
Nos. 02-3563, 02-3564 & 02-3842 5

with defendant Contreras.3 Officer Vasquez testified that in
1992 he was working as an undercover agent with the
Narcotics Covert Investigation team of the San Jose,
California Police Department and made two undercover
purchases of cocaine from a person known as “Gerardo.”
The first purchase occurred on January 27, 1992, which
involved the use of a “special employee” (SE), or informant,
to call an individual to set up a drug buy for the undercover
agent. The SE contacted Gerardo and stated that a friend
wanted to purchase approximately one half of an ounce of
cocaine. Gerardo then met the SE and Officer Vasquez at a
local restaurant, where Gerardo got into the back seat of
Officer Vasquez’s vehicle, and handed the SE a plastic pack-
age surrounded by duck tape. Officer Vasquez paid Gerardo
$250 for the package which contained 14.87 grams of cocaine.
On March 2, 1992, Officer Vasquez contacted Gerardo once
again and purchased 27.61 grams of cocaine for $500.
Officer Vasquez attempted to make a third purchase from
Gerardo but was unable to contact him. He was able to
identify Gerardo as Victor Hugo Contreras shortly after the
purchases by subpoenaing the phone records for the contact
number he was given by the SE. Officer Vasquez was also
able to identify Gerardo as Contreras in the courtroom.
On October 12, 2001, after an eight-day trial, Gregorio
Macedo was found guilty of three offenses: (1) conspiracy to
import 500 grams or more of methamphetamine or mixtures
thereof, in violation of 21 U.S.C. § 963; (2) possession with
intent to distribute between 50 and 500 grams of meth-
amphetamine or mixtures thereof, in violation of 21 U.S.C.
§ 841(a)(1); and (3) attempted possession of between 50 and
500 grams of methamphetamine or mixtures thereof, in
violation of 21 U.S.C. § 846. His co-defendant, Victor Hugo

3
Before this testimony, the district court instructed the jury that
the information conveyed by Officer Vasquez was solely to be used
as evidence on the question of intent.
6 Nos. 02-3563, 02-3564 & 02-3842

Contreras, was found guilty of conspiracy to import 500
grams or more of methamphetamine or mixtures thereof
and possession with intent to distribute between 50 and 500
grams of methamphetamine or mixtures thereof. On
September 5, 2002, Macedo was sentenced to 314 months,
while Contreras was sentenced to 210 months. The district
court also granted each defendant a one point downward
departure based on their status as deportable aliens.
The defendants allege several errors on appeal. Defendant
Macedo contends that Apprendi was violated when: (1) he
was sentenced beyond the statutory maximum for schedule
III drug violations; (2) the trial court failed to instruct the
jury that it was required to find him guilty beyond a rea-
sonable doubt of conspiring/possessing/attempting to possess
a specific amount of drugs as opposed to a range of drugs;
and (3) the district court sentenced him beyond the stat-
utory maximum by holding him responsible for 799.9 grams
of methamphetamine. Macedo also challenges the suffi-
ciency of the evidence presented at trial on all three counts
of the indictment. Defendant Contreras only asserts that
the trial court abused its discretion by admitting the
testimony of Officer Vasquez under F.R.E. 404(b) concern-
ing two prior drug sales. Finally, the government appeals
the district court’s decision to grant defendant Contreras a
one point downward departure based on his status as a
deportable foreign national.4

II. ANALYSIS

4
Defendant Contreras’s original guideline range of 235 to 293
months was thus reduced to 210 to 262 months and resulted in a
sentence of 210 months. The government does not appeal the
district court’s decision to grant defendant Macedo a one point
downward departure, though the trial court applied the same
reasoning for each defendant.
Nos. 02-3563, 02-3564 & 02-3842 7

A. Statutory Maximum Sentence and Apprendi
1. Typographical Error in the Indictment
Macedo’s primary objection stems from the government
mislabeling methamphetamine a schedule III drug (rather
than correctly labeling it a schedule II drug) in its indict-
ment. But because the indictment listed the specific drug
and quantity charged and the jury found him guilty of con-
spiring to import, possessing and attempting to possess a
specific drug type and amount, the incorrect designation of
methamphetamine as a schedule III in the indictment drug
does not implicate Apprendi.
On July 7, 1971, the Director of the Bureau of Narcotics
and Dangerous Drugs, on behalf of the Attorney General,
reclassified methamphetamine from a schedule III drug to
a schedule II drug based on its high potential for abuse rel-
ative to other substances. See 36 F.R. 12734, 12735 (July 7,
1971); 21 C.F.R. § 1308.12(d). Title 21 U.S.C. § 811(a) grants
the Attorney General the power to reclassify controlled
substances. Title 21 U.S.C. § 812(c), which lists the drug
classification schedule, classifies methamphetamine as a
schedule II drug when it is contained in “any injectable
liquid,” but classifies methamphetamine as a schedule III
drug when it is in any other form. Though previously unad-
dressed by this court directly, see United States v. Roya, 574
F.2d 386, 392-93 (7th Cir. 1978), we now find that the
reclassification of methamphetamine as a schedule II sub-
stance applies to all forms of methamphetamine in accor-
dance with 21 C.F.R. § 1308.12(d) despite the statute’s
distinction. Accord United States v. Gori, 324 F.3d 234, 240
(3d Cir. 2003) (reasoning that 21 C.F.R. § 1308.12(d) must
supercede 21 U.S.C. § 812(c)’s schedule classification as the
Attorney General acted pursuant to express authorization
and the regulation was properly promulgated); United States
v. Segler, 37 F.3d 1131, 1133 (5th Cir. 1994); United States
v. Kendall, 887 F.2d 240, 241 (9th Cir. 1989) (per curiam).
8 Nos. 02-3563, 02-3564 & 02-3842

Macedo having been found guilty of 21 U.S.C. § 841(a)(1),5
was sentenced under section 841(b)(1), which sets the de-
fault statutory maximum prison sentence based on the
amount and type of controlled substance at issue. The
statutory maximum penalty for Macedo’s conspiracy charge
is life in prison, id. at § 960(b)(1)(H),6 while the statutory
maximum penalty for his possession and attempted posses-
sion charges is forty years in prison, id. at
§ 841(b)(1)(B)(viii). However, section 841(b)(1)(D) states
that any person found guilty of violating section 841(a)(1)
as it relates to “any controlled substance in schedule III
[. . .] shall [. . .] be sentenced to a term of imprisonment of
not more than 5 years. . . .” Macedo, therefore, reasons that
because the indictment listed the drug as a schedule III
substance, he should have been sentenced to no more than
five years imprisonment under section 841(b)(1)(D).
An incorrect designation of the drug schedule in the
indictment does not mean there is an Apprendi violation
when the indictment also lists the specific drug as well as
the quantity.7 In essence, Macedo would have us ignore the

5
Section 841(a)(1) states that “it shall be unlawful for any person
to knowingly or intentionally [. . .] manufacture, distribute, or
dispense, or possess with intent to manufacture, distribute, or
dispense, a controlled substance.”
6
Title 21 U.S.C. § 960(b)(1)(H) mirrors the language of section
841(b)(1)(A)(viii).
7
The indictment charged Macedo with three counts. Count one
charged that “defendants herein, conspired among themselves and
with others known and unknown to the Grand Jury, knowingly
and intentionally to import into the United States from a place
outside the United States, a controlled substance, namely 500
grams or more of a mixture or substance containing a detectable
amount of methamphetamine, a Schedule III Narcotic Drug
Controlled Substance; In violation of Title 21, United States Code,
(continued...)
Nos. 02-3563, 02-3564 & 02-3842 9

word “methamphetamine” and the quantity designation in
the indictment, focus solely on the portion of the document
which mislabels the schedule classification, and then leap
to the conclusion that any sentence beyond the statutory
maximum for a schedule III drug (5 years) is a violation of
Apprendi. This logic is unsound.
Apprendi demands that “any fact that increases the pen-
alty for a crime beyond the prescribed statutory maximum
must be submitted to a jury, and proved beyond a reasonable
doubt.” 530 U.S. at 490. In drug sentencing cases, Apprendi
requires a drug type and amount “sufficient to trigger the
higher statutory maximum of § 841(b)(1)(A) or (B) be charged
in the indictment and found by the jury.” United States v.
Mietus, 237 F.3d 866, 874 (7th Cir. 2001). Its analysis
therefore addresses solely the appropriate decision maker
and burden of proof. United States v. Bjorkman, 270 F.3d
482, 490-92 (7th Cir. 2001); United States v. Knight, 342
F.3d 697, 710 (7th Cir. 2003).
In the case at bar, Macedo was properly indicted and the
jury was properly instructed concerning the applicable
penalties through the use of the special verdict form. The

7
(...continued)
Section 952(a).” Count three charged that “defendants herein, did
knowingly and intentionally possess with intent to distribute a
controlled substance, namely approximately 460 grams of
methamphetamine or a mixture or substance containing a
detectable amount of methamphetamine, a Schedule III Narcotic
Drug Controlled Substance; In violation of Title 21, United States
Code, Section 841(a)(1).” Count four charged that “defendants
herein, did knowingly and intentionally possess with intent to dis-
tribute a controlled substance, namely, approximately 470 grams
of methamphetamine or a mixture or substance containing a
detectable amount of methamphetamine, a Schedule III Narcotic
Drug Controlled Substance; In violation of Title 21, United States
Code, Section 841(a)(1).”
10 Nos. 02-3563, 02-3564 & 02-3842

special verdict form properly tracked the relevant language
of 21 U.S.C. § 841(b)(1). The use of this form satisfies the
edicts of Apprendi in that the drug type and amount suffi-
cient to trigger the higher statutory maximums were found
by the jury beyond a reasonable doubt. Id. The fact that the
indictment incorrectly designated methamphetamine as a
schedule III substance had no effect on the validity of the
indictment or the subsequent sentence. See United States v.
Trennell, 290 F.3d 881, 889-90 (7th Cir. 2002) (finding error
in indictment harmless where jury determined drug
quantity through the use of a special verdict form); see also
United States v. Greenwood, 974 F.2d 1449, 1472-73 (5th Cir.
1992) (finding that government erroneously labeling meth-
amphetamine a schedule III drug did not set statutory
maximum sentence at five years pursuant to § 841(b)(1)(D)
and defendant may be sentenced under § 841(b)(1)(A)(viii)
and (B)(viii) where indictment stated the specific drug type
and quantity range).8
Macedo also misconstrues Apprendi by arguing that it
requires a jury find him guilty beyond a reasonable doubt
of importing/possessing/attempting to possess a specific

8
Macedo is correct that the schedule classification of a drug may
be relevant to the maximum statutory penalty determination and
may create an Apprendi violation if the indictment refers to the
drug at issue solely in terms of its schedule classification without
referencing the drug type or amount. For example, if the indict-
ment and subsequent verdict form in this case charged Macedo
with conspiracy to import/possession/attempted possession “a
schedule III drug,” then he is correct that the statutory maximum
sentence for that crime, under Apprendi, would be 5 years as
designated by section 841(b)(1)(D). See United States v. Martin, 287
F.3d 609, 614-15 (7th Cir. 2002) (reasoning that where indictment
and verdict form stated only drug type, cocaine, without stating
drug quantity, under Apprendi defendant’s sentence could not
exceed statutory maximum for the smallest amount of cocaine
listed in § 841(b)(1)).
Nos. 02-3563, 02-3564 & 02-3842 11

amount of methamphetamine as opposed to the drug range
used by the trial court in the special verdict form. He also
takes issue with the district court’s jury instructions. The
district court initially instructed the jury that the govern-
ment need only prove that he possessed/attempted to possess
“a measurable amount” of a controlled substance to sustain
a guilty verdict of the underlying offenses. The court then,
through the use of a special verdict form, directed the jury,
if it found him guilty in the first instance, to attribute an
appropriate range of drugs to each violation.
We review a district court’s choice of jury instruction
de novo when the underlying assignment of error implicates
a question of law, such as the applicability of Apprendi;
however, general attacks on jury instructions are reviewed
for an abuse of discretion. United States v. Smith, 308 F.3d
726, 741 (7th Cir. 2002). In Smith, we explicitly held that,
even in light of Apprendi, drug quantity is not an element
of the offense and need not be proven to sustain a guilty
verdict under § 841(a)(1). Thus, the “measurable amount”
instruction is appropriate as it relates to a finding of guilt
of the underlying offenses. See id. We also explained that a
jury is not required to find a specific drug amount and the
use of a drug range in a verdict form is acceptable under
Apprendi because the elements necessary to trigger the
statutory maximum penalty are found beyond a reasonable
doubt. See id. (reasoning that because 21 U.S.C. § 841(b)
speaks in terms of drug ranges, a jury verdict which paral-
lels the statutory language is lawful); see also Mietus, 237
F.3d at 874 (finding that jury instruction which asked only
that jury find a “measurable amount” without more was
insufficient under Apprendi).
While we do not espouse the government’s “no harm no
foul” attitude concerning the typographical error in the in-
dictment, the issue remains whether, in light of the error,
Macedo was afforded sufficient notice of the charges against
him to prevent any possibility of prejudice. United States v.
12 Nos. 02-3563, 02-3564 & 02-3842

Field, 875 F.2d 130, 133 (7th Cir. 1989). Pursuant to the
logic in Field, where an error in an indictment does not go
to an element of the crime, but rather is typographical in
nature, a defendant is not prejudiced. Id. Therefore, the im-
proper designation of methamphetamine as a schedule III
drug did not prejudice the defendant as he was directed to
the applicable statute and afforded proper notice of the
charges against him.9

2. United States v. Booker and Sentencing Based
on Judge-Found Facts
While for reasons stated above we reject Macedo’s
schedule III sentencing argument (asserting that Apprendi
and the United States Sentencing Guidelines were violated
because he was sentenced beyond the statutory maximum
for a schedule III substance), we recognize that his Apprendi
claims do, in light of United States v. Booker, 125 S. Ct. 738
(2005), present colorable arguments with respect to the
propriety of two enhancements of his sentence based on
solely judge-found facts—namely, the drug quantity and
obstruction of justice enhancements.
“[T]he Sixth Amendment as construed in Blakely [v.
Washington, 124 S. Ct. 2531 (2004)] does apply to the
Sentencing Guidelines.” Booker, 125 S. Ct. at 746. Accord-
ingly, under the formerly mandatory regime, “[a]ny fact
(other than a prior conviction) which is necessary to support

9
To the extent Macedo is arguing that the jury instructions
amounted to a de facto amendment of the indictment, his asser-
tion is foreclosed by Field. The designation of methamphetamine
as a schedule III drug had no substantive effect on the indictment
as it is a fact that “need not be proven even if alleged, [. . .] and
the jury could have been instructed to ignore. . . .” Id. at 133
(quoting United States v. Skelly, 501 F.2d 447, 453 (7th Cir.
1974)).
Nos. 02-3563, 02-3564 & 02-3842 13

a sentence exceeding the maximum authorized by the facts
established by a plea of guilty or a jury verdict must be
admitted by the defendant or proved to a jury beyond a
reasonable doubt.” Id. at 756.

a. Drug Quantity Enhancement
Macedo first argues that the district court erred by
enhancing his sentence based on a factual finding made
solely by the sentencing judge with respect to the purity
and quantity of methamphetamine involved in his offenses.
Because this matter appears before us on direct review, and
because Macedo raised an objection to his sentence based on
Apprendi v. New Jersey, 530 U.S. 466 (2000) before the
district court (see Defendant’s Objection’s [sic] to
Presentence Investigation Report at 2-3, United States v.
Macedo, filed July 1, 2002 (No. 02-3536)), our standard of
review is plenary. See Booker, 125 S. Ct. at 769.
Pursuant to special verdict forms, the jury here found
Macedo guilty beyond a reasonable doubt of, among other
charges, (1) “conspiracy to import 500 grams or more of
mixtures containing a detectible amount of methamphet-
amine,” (2) possession of “50 grams or more, but less than
500 grams of mixtures containing a detectible amount of
methamphetamine,” and (3) attempt to possess “50 grams
or more, but less than 500 grams of mixtures containing a
detectible amount of methamphetamine.” Thus, in total the
jury found that Macedo’s offenses of conviction involved a
total of 600 or more grams of mixtures containing metham-
phetamine. Under Booker, these findings proven to the jury
beyond a reasonable doubt provide a legitimate basis upon
which a judge may impose sentence.
We turn now to the district court’s application of the
Sentencing Guidelines. In this case, we analyze the district
court’s use of the Guidelines not to assess the propriety of
their application—for after Booker they serve no longer as
14 Nos. 02-3563, 02-3564 & 02-3842

a mandatory prescription but rather as an advisory refer-
ence, Booker, 125 S. Ct. at 756-57—but rather to ascertain
those facts upon which the district court felt authorized, even
obliged, to base its sentence of Macedo. The Guidelines rec-
ognize various qualities of methamphetamine—“meth-
amphetamine,” “methamphetamine (actual),” and “Ice.” See
generally U.S.S.G. § 2D1.1.10 These distinctions are of
appreciable significance under the Guidelines’ regime, because
the quality of methamphetamine with which a defendant is
found to have been involved can help determine the base
offense level assigned to the defendant for purposes of calcu-
lating his sentence. Indeed, the base offense level is a factor
upon which Guidelines sentencing is predominantly based.
As the findings catalogued above reveal, the jury found

10
Notes to the Section 2D1.1(c) Drug Quantity Table define the
terms “methamphetamine,” “methamphetamine (actual),” and
“Ice”:
(A) Unless otherwise specified, the weight of a controlled
substance set forth in the table refers to the entire
weight of any mixture or substance containing a
detectible amount of the controlled substance [i.e.,
“Methamphetamine”]. . . .
(B) The term[ ] . . . “Methamphetamine (actual)” refer[s]
to the weight of the controlled substance, itself,
contained in the mixture or substance. For example,
a mixture weighing 10 grams containing
[Methamphetamine] at 50% purity contains 5 grams
of [Methamphetamine] (actual). In the case of a mix-
ture or substance containing . . . methamphetamine,
use the offense level determined by the entire weight
of the mixture or substance, or the offense level de-
termined by the weight of the . . . methamphetamine
(actual), whichever is greater. . . .
(C) “Ice,” for the purposes of this guideline, means a mix-
ture or substance containing d-methamphetamine
hydrochloride of at least 80% purity.
Nos. 02-3563, 02-3564 & 02-3842 15

Macedo guilty of offenses involving 600 grams or more of
plain old “methamphetamine”—not “methamphetamine (ac-
tual)” or “Ice.” Had the district court relied solely on those
jury findings, Macedo’s base offense level under the Guide-
lines would have been 32. See U.S.S.G. §§ 2D1.1(a)(3) and
2D1.1(c)(4) (providing a base level of 32 for offenses involv-
ing “[a]t least 500 G but less than 1.5 KG of
Methamphetamine”). The district court, however, went
further. At sentencing it found by a preponderance of the
evidence that the actual weight of the charged mixtures was
878.8 grams (based on uncontested results of government
lab analysis) and that 91% of those mixtures, or 799.7
grams, constituted “methamphetamine (actual).” Based on
these supplemental factual findings, the district court
sentenced Macedo pursuant to Sections 2D1.1(a)(3) and
2D1.1(c)(4) of the Guidelines, which carries with them a
base offense level of 36 for offenses involving “at least 500
G but less than 1.5 KG of Methamphetamine (actual), or at
least 500 G but less than 1.5 KG of ‘Ice.’ ” (emphasis added).
Thus, based on solely judge-found facts, the district court
increased Macedo’s base offense level by four levels (from 32
to 36). Such sentencing in reliance on supplemental facts not
admitted by Macedo or proven to the jury beyond a reasonable
doubt—namely, involvement with 799.7 grams of metham-
phetamine (actual) as opposed to involvement with merely
600 grams of methamphetamine—squarely offends our new
understanding of the Sixth Amendment as divined by
Booker.

b. Obstruction of Justice Enhancement
Macedo also argues that the district court erred by im-
posing a two-level increase in calculating his adjusted offense
level—thereby enhancing his ultimate sentence—based on
an obstruction of justice finding made solely by the sen-
tencing judge. Despite the government’s arguments to the
contrary, Macedo has not waived this argument by failing
to argue the obstruction enhancement on appeal. In a direct
16 Nos. 02-3563, 02-3564 & 02-3842

appeal, a defendant might preserve his Blakely and Booker
arguments by raising them in subsequent filings. See
United States v. Henningsen, 387 F.3d 585, 591 (7th Cir.
2004) (“Although [the defendant] did not raise the issue of
constitutionality in his brief, he made notice of the Blakely
and Booker decisions in a subsequent filing and raised the
issue during argument. In light of the uncertainty surround-
ing this issue and the questionable constitutionality of [the
defendant’s] sentencing enhancement, we do not find that
[the defendant] has waived his right to challenge the valid-
ity of the district court’s sentencing enhancement”); see also
United States v. Pree, 384 F.3d 378, 396 (7th Cir. 2004)
(“Given the precedent in this circuit prior to Blakely, we
think it would be unfair to characterize [the defendant] as
having waived a challenge to the validity of her sentencing
enhancement.”). Macedo has done so here by virtue of filing
a petition for rehearing.
Macedo has, however, forfeited his appeal of the district
court’s imposition of the obstruction enhancement by failing
to raise the argument before the court below. United States
v. Olano, 507 U.S. 725, 731-32 (1993) (“ ‘No procedural prin-
ciple is more familiar to this Court than that a constitu-
tional right,’ or a right of any other sort, ‘may be forfeited in
criminal as well as civil cases by the failure to make timely
assertion of the right before a tribunal having jurisdiction
to determine it.’ ”) (quoting Yakus v. United States, 321 U.S.
414, 444 (1944)). Accordingly, and in contrast to his objection
to sentencing based on the improper imposition of a drug
quantity enhancement, we review Macedo’s challenge to the
obstruction of justice enhancement for plain error. United
States v. Paladino, 401 F.3d 471, 481 (7th Cir. 2005). “Under
[the plain error] test, before an appellate court can correct an
error not raised at trial, there must be (1) ‘error,’ (2) that is
‘plain,’ and (3) that ‘affect[s] substantial rights.’ ” United
States v. Cotton, 535 U.S. 625, 631 (2002) (quoting Johnson
v. United States, 520 U.S. 461, 466-67 (1997)). “If all three
Nos. 02-3563, 02-3564 & 02-3842 17

conditions are met, an appellate court may then exercise its
discretion to notice a forfeited error, but only if (4) the error
seriously affect[s] the fairness, integrity, or public reputa-
tion of judicial proceedings.” Id. (quoting Johnson, 520 U.S.
at 467).
Enhancement of Macedo’s sentence based on facts not ad-
mitted by the defendant or proven to a jury beyond a rea-
sonable doubt does, under the new Booker regime, constitute
“error.” Furthermore, that error was plain. “ ‘Plain’ is synon-
ymous with ‘clear’ or, equivalently, ‘obvious.’ ” Olano, 507
U.S. at 734. At the time of Macedo’s sentencing,
September 11, 2002, the Sixth Amendment and the reason-
ing of Apprendi were not yet understood to apply to the
Federal Sentencing Guidelines. Cf. Blakely v. Washington,
124 S. Ct. 2531 (2004) (issued on June 24, 2004); Booker,
supra (issued on January 12, 2005). However, “where the
law at the time of trial was settled and clearly contrary to
the law at the time of appeal[,] it is enough that an error be
‘plain’ at the time of appellate consideration.” Johnson, 520
U.S. at 468 (emphasis added). Thus, while the propriety of
imposing sentence enhancements free from the constraints
of the Sixth Amendment was at the time of Macedo’s
sentencing settled, that practice is today and at the time of
this appeal clearly contrary to the law as set forth by
Booker. Accordingly, the error of enhancing Macedo’s sen-
tence based on findings of obstruction of justice found solely
by the sentencing judge is plain.
As we recently noted in Paladino, 401 F.3d at 481, the
difference between the third and fourth prongs of the plain
error standard “is not entirely clear.” While the third
element requires the error to have been “prejudicial,” in
that it “affected the outcome of the district court proceed-
ings,” Olano, 507 U.S. at 734, the fourth element requires
that the uncorrected error be “intolerable,” or result in a
“miscarriage of justice,” Paladino, 401 F.3d at 481 (citing
cases). Indeed, the third prong feeds into the fourth, in that
18 Nos. 02-3563, 02-3564 & 02-3842

there cannot be a miscarriage of justice without prejudice
to the defendant. Conversely, “[a]n error can be prejudicial
without being intolerable, because it might be apparent
that a retrial or a resentencing would lead to the same
result.” Id. Here we can and have predetermined that if the
defendant has been prejudiced by an illegal sentence, then
allowing that illegal sentence to stand would constitute a
miscarriage of justice. Id. at 483 (“It is a miscarriage of
justice to give a person an illegal sentence that increases
his punishment, just as it is to convict an innocent per-
son.”); United States v. Pawlinski, 374 F.3d 536, 541 (7th
Cir. 2004) (“[T]he entry of an illegal sentence is a serious
error routinely corrected on plain error review.”). But what
we cannot do on plain error review is divine with requisite
certainty whether the district court, operating under
broader post-Booker discretion, would have sentenced the
defendant any differently. Thus, to resolve this dilemma
and complete our plain error analysis, normally we, “while
retaining jurisdiction of the appeal, order a limited remand
to permit the sentencing judge to determine whether he
would (if required to resentence) reimpose his original
sentence.” Paladino, 401 F.3d at 483-84.

c. Disposition
We need not, however, engage the district court in such
an intermediate inquiry here. Because we find grounds for
remand under our broader standard of plenary review
based on the drug quantity enhancement, this case may be
remanded to the district court without reservation. Accord-
ingly, we vacate Macedo’s sentence and remand his case for
resentencing consistent with this opinion and the Supreme
Court’s recent decision in Booker.

B. Sufficiency of the Evidence
Nos. 02-3563, 02-3564 & 02-3842 19

Macedo contends that the government failed to present
sufficient evidence to support his conviction on all three
charges in the indictment. On appeal, we review the evi-
dence in the light most favorable to the prosecution and will
reverse a jury verdict only when the record “is devoid of any
evidence, regardless of how it is weighed, from which a jury
could find the defendant[ ] guilty beyond a reasonable
doubt.” United States v. Hernandez, 330 F.3d 964, 976 (7th
Cir. 2003) (citing United States v. Johnson, 26 F.3d 669, 684
(7th Cir. 1994)). While a sufficiency of the evidence claim is
not untenable on appeal, it is nevertheless a steep hill to
climb. Id. (citing United States v. Frazier, 213 F.3d 409, 416
(7th Cir. 2000)).
In essence, Macedo takes issue with the propriety of re-
lying on coconspirator testimony to support his convictions.
He argues that Maldonado and Mendez’s testimony was
conflicting, inconsistent and biased, and absent the testi-
mony, there is no evidence linking him to this conspiracy
beyond his mere presence at the airport. However, the con-
flicts or inconsistencies Macedo highlights are immaterial.11
With regard to Maldonado and Mendez’s potential bias, this
court has held that “[u]nless testimony is inherently unbe-
lievable, a guilty verdict may be based on the testimony of
a coconspirator testifying pursuant to a plea agreement:
Credibility is for the jury, not this court to determine.”
United States v. Jewel, 947 F.2d 224, 231 (7th Cir. 1991)
(internal quotations and citations omitted).

11
For example, he points to discrepancies between Mendez’s
grand jury testimony, where he stated that he was to receive the
full $1500 from Contreras and Macedo in the United States, with
his in court testimony, where he stated that he was to be paid in
two installments of $750. He also suggests Maldonado’s testimony
is unreliable given Maldonado’s statements to the grand jury that
he exchanged the methamphetamine-laden shoes in Contreras’s
car as compared to direct testimony where he stated the exchange
occurred in Contreras’s home.
20 Nos. 02-3563, 02-3564 & 02-3842

Reviewing the record, we do not find that Maldonado and
Mendez’s testimony was “inherently unbelievable.” Id. Quite
the contrary, it was corroborated by the direct evidence
presented at trial. The government recovered Mendez’s
methamphetamine-laden shoes from the motel room rented
by Macedo. Agents observed the meeting between the four
men on January 20, 2001, the day of the arrest. Agent
Michael Heene witnessed Maldonado place a call to
Contreras and Macedo which led to the meeting at O’Hare
Airport. Accordingly, we will not disregard the testimony of
his coconspirators.
Taking all the evidence presented to the jury into account,
it had ample evidence to support its guilty verdict on all
three charges in the indictment. To sustain a conspiracy
conviction, the government must prove that “two or more
persons joined together for the purpose of committing a
criminal act and that the charged party knew of and
intended to join the agreement.” United States v. Adkins,
274 F.3d 444, 450 (7th Cir. 2001). Further, a jury is not
limited to direct evidence (though here the record contains
a plethora) and may “find an agreement to conspire based
upon circumstantial evidence and reasonable inferences
drawn [from] the relationship of the parties, their overt acts,
and the totality of their conduct.” United States v. Turner,
93 F.3d 276, 282 (7th Cir. 1996) (quoting United States v.
Mojica, 984 F.2d 1426, 1432 (7th Cir. 1993)).
The jury heard the following evidence: (1) Macedo traveled
to the airport to pick up Mendez and Maldonado; (2)
Macedo paid for the new shoes Mendez exchanged for the
shoes containing the drugs; (3) he paid for the motel room
from which the drugs were subsequently recovered; (4) he
told Maldonado that he would purchase his return ticket to
Mexico; and (5) his cellular phone number was given to both
coconspirators. See United States v. Gutierrez, 978 F.2d 1463,
1469 (7th Cir. 1992) (“[A] single act will suffice if the
circumstances permit the inference that the presence or act
was intended to advance the ends of the conspiracy.”). Thus,
Nos. 02-3563, 02-3564 & 02-3842 21

Macedo’s involvement traversed the line from mere pres-
ence to participant. See United States v. Albarran, 233 F.3d
972, 977 (7th Cir. 2000) (reasoning that a government need
only prove a “participatory link” between the defendant and
the conspiracy). The jury had sufficient evidence to find that
Macedo knew of and intended to enter into an agreement
with Contreras, Maldonado and Mendez to engage in the
criminal act of importing methamphetamine.
The evidence also supports the jury’s verdict with regard
to Macedo’s possession with intent to distribute and at-
tempted possession charges. Under 21 U.S.C. § 841(a)(1),
the government must prove that Macedo (1) knowingly or
intentionally possessed the methamphetamine, (2) possessed
it with the intent to distribute it, and (3) knew that meth-
amphetamine was a controlled substance. United States v.
Griffin, 194 F.3d 808, 816 (7th Cir. 1999). Mendez testified
that upon his arrival in the United States, he gave the shoes
containing the methamphetamine to Macedo who determined
it was safer to leave the shoes in the motel room which
Macedo secured. Thus, the jury could have reasonably found
that Macedo actually possessed the drugs, as well as
constructively possessed them. See United States v. Perlaza,
818 F.2d 1354, 1360 (7th Cir. 1987) (finding that evidence
of registration and control over a hotel room containing
drugs may be sufficient to find constructive possession of
drugs); see also United States v. Garrett, 903 F.2d 1105, 1112
(7th Cir. 1990) (holding that constructive possession is suf-
ficient to sustain a conviction under 21 U.S.C. § 841(a)(1)).
Furthermore, the jury could have reasonably found that
Macedo intended to distribute the methamphetamine based
on the large quantity seized and the testimony of his co-
conspirators.

C. Admission of Prior Bad Act Evidence Under
F.R.E. 404(b)
22 Nos. 02-3563, 02-3564 & 02-3842

Defendant Contreras challenges the decision of the district
court to admit the testimony of Officer Vasquez concerning
two prior drug sales which occurred in 1992 as dissimilar
and too remote in time. We review a district court’s decision
to admit evidence pursuant to Rule 404(b) of the Federal
Rules of Evidence for abuse of discretion. United States v.
Anifowoshe, 307 F.3d 643, 646 (7th Cir. 2002). Rule 404(b)
prohibits the use of a defendant’s prior bad acts as propen-
sity evidence while permitting its use to prove “motive,
opportunity, intent, preparation, plan, knowledge, identity,
or absence of mistake or accident.” Fed. R. Evid. 404(b).
We have long recognized that the permissible use of prior
bad act evidence to prove intent or lack of mistake may
have the potential impermissible side effect of allowing the
jury to infer criminal propensity. See United States v.
Beasley, 809 F.2d 1273, 1278 (7th Cir. 1987) (“When the
same evidence has legitimate and forbidden uses, when the
introduction is valuable yet dangerous, the district judge
has great discretion.”). To address these twin concerns, we
have reasoned that evidence is properly admitted if the
government is able to show that:
(1) the evidence is directed toward establishing a
matter in issue other than the defendant’s propen-
sity to commit the crime charged, (2) the evidence
shows that the other act is similar enough and close
in time to be relevant to the matter in issue, (3) the
evidence is sufficient to support a jury finding that
the defendant committed the similar act, and (4)
the probative value of the evidence is not substan-
tially outweighed by the danger of unfair prejudice.
United States v. Wash, 231 F.3d 366, 370 (7th Cir. 2000)
(quoting United States v. Wilson, 31 F.3d 510, 514-15 (7th
Cir. 1994)). Furthermore, when a defendant is charged with
a specific intent crime, such as possession with intent to
distribute, we have reasoned that evidence of past action is
Nos. 02-3563, 02-3564 & 02-3842 23

probative if used to establish an essential element of the
crime charged. Id.; United States v. Long, 86 F.3d 81, 84
(7th Cir. 1996).
Though this is a close case, we cannot find that the
district court abused its discretion by admitting the testi-
mony of Officer Vasquez. Contreras correctly points out that
there is a nine-year gap between the 1992 drug sales and
the 2001 charges. While we acknowledge that nine years is
a substantial amount of time, the temporal proximity of the
prior acts to the current charge is not alone determinative
of admissibility. See United States v. Wimberly, 60 F.3d 281,
285 (7th Cir. 1995) (admitting prior bad act evidence that
occurred thirteen years prior to charge when evidence was
highly reliable and relevant to credibility); United States v.
Mounts, 35 F.3d 1208, 1214 (7th Cir. 1994) (permitting
admission of drug purchase which occurred seven years
prior to arrest to prove element of intent).
Defendant’s argument that the events are not sufficiently
similar because the 1992 transaction involved cocaine while
his current conviction involves methamphetamine is also
unsupported by this circuit’s precedent. The similarity
inquiry focuses on the purpose for which evidence is offered.
Long, 86 F.3d at 84. The 1992 cocaine sales were offered to
prove Contreras’s intent to possess distribution amounts of
illicit drugs. See United States v. Hernandez, 84 F.3d 931,
935 (7th Cir. 1996) (finding sufficient similarity when
different drugs are at issue because both instances involved
“distribution amounts of drugs and illicit transport”); Wash,
231 F.3d at 370 (finding sufficient similarity when prior bad
acts and current charge both involve “possessing distribu-
tion amounts of drugs”).
The evidence submitted by Officer Vasquez was unques-
tionably reliable. The record also reveals the district court’s
thorough discussion of Contreras’s theory of the case, i.e.,
that he lacked the intent to enter into a conspiracy to im-
24 Nos. 02-3563, 02-3564 & 02-3842

port or possess methamphetamine or the knowledge that
one existed and was simply present at the airport that day
by happenstance. (During closing arguments his attorney
went so far as to call him a “dupe” or fall guy.) This theory
coupled with the government’s need to prove an essential
element of the case, i.e., that the defendant acted with the
requisite specific intent, supports the district court’s decision
to admit the prior bad acts.
Further, any prejudicial effect on the defendant was les-
sened by the trial court’s limiting instruction that the evi-
dence was solely to be used to evaluate the issue of intent.
United States v. Tringali, 71 F.3d 1375, 1379 (7th Cir. 1995).
Finally, were we to err on the side of caution and deem this
testimony’s admission in error, it would undoubtedly be
harmless as the weight of the evidence against Contreras
was overwhelming. See United States v. Coleman, 179 F.3d
1056, 1062 (7th Cir. 1999).

D. Downward Departure Based on Alien Status
The government appeals the district court’s decision to
grant defendant Contreras a one point downward departure
based on its finding that his alien status and deportability
would cause the conditions of confinement to be more
“onerous.” The district court found that Contreras would
suffer a substantial hardship because the Bureau of Prison’s
(BOP) placement policy for deportable aliens “limits the
discretion of the Bureau of Prisons to take into account
among other things factors that would warrant more hu-
manitarian designations like family and other matters.”
Sent. Trans. at 6-16.12

12
Contreras argues that the district court made the following
findings: (1) Contreras would not be able to serve any time in a
(continued...)
Nos. 02-3563, 02-3564 & 02-3842 25

We review a district court’s decision to grant a downward
departure de novo. United States v. Mallon, 345 F.3d 943,
945-47 (7th Cir. 2003) (discussing the retroactive applica-
tion of section 401(d) of the Prosecutorial Remedies and
Tools Against the Exploitation of Children Today Act of
2003 (PROTECT Act), Pub. L. No. 108-21, 117 Stat. 650,
which amended 18 U.S.C. § 3742(e)’s prior standard of re-
view); see also United States v. Griffin, 344 F.3d 714, 718
(7th Cir. 2003) (discussing effect of PROTECT Act on district
court’s decision to upward depart). This court has held that
“the defendant’s status as a deportable alien is relevant
only insofar as it may lead to conditions of confinement, or
other incidents of punishment, that are substantially more
onerous than the framers of the guidelines contemplated in
fixing the punishment range for the defendant’s offense.”
United States v. Guzman, 236 F.3d 830, 834 (7th Cir. 2001)
(emphasis added).
We then further explained that it is permissible “in
exceptional circumstances” to take into account a defendant’s
alienage when assessing whether his status makes his con-
ditions of confinement “harsher by disentitling a defendant
to serve any part of his sentence in a halfway house, mini-
mum security prison, or intensive confinement center, so
that the same nominal prison sentence would be, quite apart
from the sequel of deportation, a more severe punishment
than if the defendant were a citizen.” Id. More recently, we
explained that downward departures based solely on an

12
(...continued)
halfway house; (2) he would not be eligible for a minimum security
facility because he would have to be sent to one of three facilities
able to conduct deportation hearings; and (3) the high likelihood
he would be incarcerated in an INS camp which is “much harder
time.” After reviewing the record, we find that the district court
made no such findings. Rather these points were advanced by
Contreras in his argument to the court below.
26 Nos. 02-3563, 02-3564 & 02-3842

alien’s loss of “end-of-sentence modifications,” such as
halfway house placement, “cannot be viewed as a term of
imprisonment ‘substantially more onerous’ than the
guidelines contemplated in fixing a punishment for a
crime.” United States v. Meza-Urtado, 351 F.3d 301, 305
(7th Cir. 2003); but see Mallon, 345 F.3d at 949 (“A prisoner
who is ineligible for transfer, and as a result of alienage
becomes ineligible for transitional release, suffers a real
disadvantage.”).
The government is correct that the district court based its
decision on the BOP’s policy which places alien prisoners in
certain facilities. Any defendant, citizen or alien, may be
placed far from loved ones and family and thus this circum-
stance is not substantially more onerous than contemplated
by the guidelines. Furthermore, application of this logic
would amount to a per se downward departure for any de-
portable alien, which standing alone, is an impermissible
basis for granting a downward departure. United States v.
Gallo-Vasquez, 284 F.3d 780 (7th Cir. 2002) (remanding
based on district court’s failure to make a sufficient showing
that defendant’s situation was “exceptional”). Contreras
must therefore be resentenced.

III. CONCLUSION
For the reasons stated above, judgment of defendant
Macedo’s conviction is AFFIRMED, however, his sentence is
VACATED and his case is REMANDED for resentencing con-
sistent with this opinion. Defendant Contreras’s judgment
of conviction is also AFFIRMED, however, his sentence too is
VACATED and his case is REMANDED for resentencing
consistent with this opinion.

A true Copy:
Teste:
Nos. 02-3563, 02-3564 & 02-3842 27

________________________________
Clerk of the United States Court of
Appeals for the Seventh Circuit

USCA-02-C-0072—4-14-05