United States v. Goodhue

United States Court of Appeals
For the First Circuit

No. 05-2825

UNITED STATES OF AMERICA,

Appellee,

v.

KEITH GOODHUE,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF MASSACHUSETTS

[Hon. F. Dennis Saylor, U.S. District Judge]

Before

Lynch and Howard, Circuit Judges,
and Young,* District Judge.

Todd A. Bussert for appellant.
Cynthia A. Young, Assistant U.S. Attorney, with whom Michael
J. Sullivan, United States Attorney, and Paul G. Casey, Assistant
U.S. Attorney, were on brief, for appellee.

May 16, 2007

*
Of the District of Massachusetts, sitting by designation.
 YOUNG, District Judge. Keith Goodhue (“Goodhue”) here

challenges his criminal sentence. The government concedes that the

sentence needs recalculation under the appropriate Criminal History

Category so remand is in order. Goodhue further argues that the

district court erred when it calculated his Base Offense Level from

the total weight of a mixture containing undetermined amounts of

methamphetamine precursor components. We find merit to Goodhue’s

underlying contention that the government ought isolate and

separately weigh the controlled substances in such a mixture or

demonstrate the inability to do so. Nevertheless, we hold that the

district court did not commit plain error in approximating the

actual weight of the precursor components.

I. Factual and Procedural History

On November 11, 2003, Goodhue discovered his wife lying

unconscious in the bedroom of their apartment. Goodhue promptly

called 911. The paramedics and the police responded, and Goodhue

led them to the bedroom. The paramedics were unable to resuscitate

Goodhue’s wife so they transported her to the hospital, where she

later recovered.

While in the bedroom, the police observed a stained glass

tube that they suspected to be drug paraphernalia. The officers

also noticed children’s beds, toys, and clothes and learned that

two small children slept in the room. The police then conducted,

with Goodhue’s assistance, a search for needles and syringes that

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could pose a danger to young children. The police discovered three

needles and syringes in a dresser drawer, a glass evaporator with

an attached rubber hose, a glass jar with coffee filters stained

red, and a bottle of lye.

The police read Goodhue his Miranda rights, and he signed

a consent form to search the rest of the residence. Goodhue led

them to more drug paraphernalia. The various liquids and powders

seized were submitted to the Massachusetts State Police Crime

Laboratory for analysis. The crime laboratory analysis of the

substances seized from Goodhue’s home revealed the following

controlled substances: 65.87 grams of red phosphorous; 116.37 grams

of iodine; > 304.97 grams of Red Devil Lye; 4.64 grams of a mixture

containing ephedrine; and 48.44 grams of a mixture containing

pseudoephedrine. Ephedrine and pseudoephedrine are common

precursor chemicals for the manufacture of methamphetamine.

On July 27, 2005, Goodhue pleaded guilty in federal

district court to a one-count felony information for possession of

the listed chemicals with intent to manufacture methamphetamine in

contravention of 21 U.S.C. § 841(c)(1). On November 21, 2005, the

district court sentenced him to imprisonment for 63 months followed

by three years’ supervised release.

Goodhue raises the following three issues on his timely

appeal: 1) that the district court erred in the calculation of his

Base Offense Level under the United States Sentencing Guidelines §

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2D1.11; 2) that the district court incorrectly determined his

Criminal History Category; and 3) that the resulting sentence was

not reasonable in light of the factors enumerated in 18 U.S.C. §

3553(a). Appellant Br. at 1.

The government concedes that the district court

miscalculated Goodhue’s Criminal History Category and requests a

limited remand to correct this aspect of the sentence.1 Appellee

Br. at 16 n.8. In light of this concession, remand is proper. On

remand, the district court may reconsider the entire sentence,

making review for reasonableness premature. See United States v.

Blasini-Lluberas, 169 F.3d 57, 68 (1st Cir. 1999). As a result,

Goodhue’s sole remaining issue on appeal is whether the district

court correctly calculated his Base Offense Level.

We have jurisdiction over this sentencing appeal pursuant

to 18 U.S.C. § 3742(a).

II. Discussion

A. Standard of Review

An issue is preserved for appeal when the appellant

adequately preserved the issue through a timely and contemporaneous

1
Goodhue’s Criminal History Category was calculated in the
PSR at II based on three criminal history points. Two of the
criminal history points were added based upon a finding that
Goodhue “committed the instant offense while under any criminal
justice sentence.” U.S. Sentencing Guidelines Manual § 4A1.1(d)
(2004). Both Goodhue and the government agree that this finding
was in error because his sentence for driving without a license or
with a revoked or suspended license did not satisfy this
definition.
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objection to the district court. See United States v. Wihbey, 75

F.3d 761, 771 (1st Cir. 1996). When an issue has been preserved,

review of a district court’s factual findings relevant to a

sentencing calculation is for clear error. United States v. Alli,

444 F.3d 34, 37 (1st Cir. 2006). Review of a district court’s

interpretation and application of the United States Sentencing

Guidelines is de novo. United States v. Robinson, 433 F.3d 31, 35

(1st Cir. 2005).

An issue is “waived,” however, where the appellant

“intentionally relinquishes or abandons it.” United States v.

Rodriguez, 311 F.3d 435, 437 (1st Cir. 2002). An appellate court

will normally not review waived issues. Id. Alternatively, an

appellant “forfeits” his claim by failing “to make a timely

assertion of a right . . . .” Id. Appellate review of a forfeited

claim is for plain error only, id., and such a standard can be

satisfied only if “(1) [] an error occurred (2) which was clear or

obvious and which not only (3) affected the defendant’s substantial

rights, but also (4) seriously impaired the fairness, integrity, or

public reputation of [the] judicial proceedings.” United States v.

Duarte, 246 F.3d 56, 60 (1st Cir. 2001); see also United States v.

Riggs, 287 F.3d 221, 224 (1st Cir. 2002); United States v. Olivier-

Diaz, 13 F.3d 1, 5 (1st Cir. 1993).

The standard of review that will apply to Goodhue’s

appeal thus turns on whether he adequately preserved his claim

before the district court. Accordingly, we scrutinize Goodhue’s
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arguments on appeal to determine if he made the same arguments

below.

Goodhue claims on appeal that the district court erred

when it used the aggregate weight of the entire mixture containing

undetermined amounts of ephedrine and pseudoephedrine to calculate

the sentence. Appellant Br. at 16-18. The district court

calculated the applicable advisory guideline range under section

2D1.11 by starting from a drug weight of 53.08 grams -- the weight

of the entire mixture2 -- instead of the isolated weights of the

ephedrine and pseudoephedrine components within the mixtures.

Sentencing Transcript (“S. Tr.”) at 6:18-7:1; 22:8-9. In so doing,

the district judge calculated the Base Offense Level at 28, but

expressed concern with this approach. Id. at 22:11-23:13.

At sentencing, the government advocated the position that

when a mixture contains undetermined or undeterminable amounts of

ephedrine and pseudoephedrine, the district court ought simply

apply the section 2D1.11 tables to the aggregate weight of the

mixtures. Id. at 9:3-25; 12:11-15. Goodhue’s trial counsel

objected to this approach. Id. at 16:4-17:6. Trial counsel argued

that the district court must not apply the total weight of the

mixture to the tables, but ought instead approximate the weight of

the pure precursor components through “any reasonable method.” Id.

2
The reference to the entire mixture includes the 4.64 grams
of a mixture containing ephedrine and the 48.44 grams of a mixture
containing pseudoephedrine as determined by the state laboratory
results.
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at 16:4-10. The reference to “any reasonable method” sought to

direct the district court to Application Note 1 of section 2D1.1,3

which allows the court to estimate the weight of drug quantity when

the components cannot be segregated. U.S. Sentencing Guidelines

Manual § 2D1.1 cmt. n.1 (2004).4

Goodhue’s trial counsel argued that the “reasonable

method” that the court ought follow was the “yield analysis” of

United States v. Barnett, 989 F.2d 546 (1st Cir. 1993), which

calculated how much methamphetamine (actual)5 could be processed

from pseudoephedrine. S. Tr. at 17:3-16; Barnett, 989 F.2d at 553.

The approximated amount is then applied to the methamphetamine

(actual) drug quantity table. As trial counsel would have it, the

court would utilize a ratio of one gram of mixture to 0.58 grams of

methamphetamine (actual). S. Tr. at 17:2-16; Barnett, 989 F.2d at

553. Trial counsel objected, therefore, not to using the 53.08

3
Section 2D1.1 addresses the “Unlawful Manufacturing,
Importing, Exporting, Trafficking, or Possession; Continuing
Criminal Enterprise” by assigning a base offense level through the
application of predetermined ranges to drug weights.
4
The language of this Note was added effective November 1,
1993 by Amendment 484. The amendment’s purpose was to address a
circuit split regarding the term “mixture or substance” by
providing expressly that the term does not include portions of a
drug mixture that must be separated from the controlled substance
before it is used. U.S. Sentencing Guidelines Manual § 2D1.1, app.
C, amend. 484 (2004).
5
The term “methamphetamine (actual)” refers to the weight of
the controlled substance itself contained in the mixture or
substance. U.S. Sentencing Guidelines Manual § 2D1.1 n.B (2004).
The term methamphetamine with no qualifier refers to a mixture of
methamphetamine and other substances. See id., § 2D1.1 n.A.
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grams of mixture as the starting point of the sentencing

calculation, but to applying the aggregate weight of the mixture to

the ephedrine and pseudoephedrine tables in section 2D1.11 instead

of the approximated yield of methamphetamine (actual) under section

2D1.1.

The district court recognized, however, that the trial

counsel’s proposed yield analysis would produce 30.78 grams of

methamphetamine (actual) from the 53.08 grams of mixture. S. Tr.

at 17:14-19. Under section 2D1.1, this would still result in a

Base Offense Level of 28. Id. at 17:18-19. Faced with this

calculation, trial counsel conceded that he incorrectly read and

applied the Guidelines. Id. at 18:23-19:1.6

Goodhue now, on appeal and with new counsel, seeks to re-

characterize the trial counsel’s objection raised to the district

court as one challenging the use of the 53.08 grams of mixture as

the starting point of the calculation. Compare Appellant Br. at

16-18, with S. Tr. at 16:4-17:6. As described above, Goodhue’s

trial counsel bypassed a challenge on that threshold ground and

focused instead on a legal theory as to how the Guidelines ought

apply to the 53.08 grams of mixture. See S. Tr. at 16:3-17:6. By

6
Even if a yield analysis were appropriate, it is not clear
that 0.58 would be the appropriate measure since Barnett concerned
pure pseudoephedrine as the precursor. Here, there is not only an
impure mixture of pseudoephedrine but also an impure mixture of
ephedrine. We need not decide, however, what the appropriate yield
would be in such a situation because the parties did not raise this
issue.
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failing to object to the use of the aggregate weight of the

mixture, Goodhue’s trial counsel forfeited that issue for appeal.

See United States v. Figuereo, 404 F.3d 537, 540, 540 n.3 (1st Cir.

2005) (applying a plain error review where a defendant objected at

sentencing but on a basis not before the appellate panel). As a

result, we will review only for plain error. See id. at 540.

B. The Base Offense Level Calculation

1. Review of the District Court’s Interpretation of
Section 2D1.11

The fulcrum for our plain error review of the district

court’s calculation of Goodhue’s Base Offense Level is whether any

error was clear or obvious. See United States v. Olano, 507 U.S.

725, 734 (1993); Duarte, 246 F.3d at 60. “Where the error

defendant asserts on appeal depends upon a factual finding the

defendant neglected to ask the district court to make, the error

cannot be ‘clear’ or ‘obvious’ unless the desired factual finding

is the only one rationally supported by the record below.” United

States v. Donnelly, 370 F.3d 87, 95 (1st Cir. 2004) (quoting

Olivier-Diaz, 13 F.3d at 5). With respect to matters of law, an

error will not be clear or obvious where the challenged issue of

law is unsettled. See Connelly v. Hyundai Motor Co., 351 F.3d 535,

546 (1st Cir. 2003); United States v. Marino, 277 F.3d 11, 32 (1st

Cir. 2002).

Here, Goodhue challenges the district court’s calculation

of the Base Offense Level on two grounds. First, Goodhue

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speculates that had the district court conducted a factual finding

as to the weights of ephedrine and pseudoephedrine, such a factual

finding could have resulted in a lower Base Offense Level.

Appellant Br. at 17. This challenge is akin to an argument that

the district court ought to have held an evidentiary hearing on the

weight of the pure precursor chemicals. Such an argument has no

legal traction.

In United States v. DeCologero, 821 F.2d 39 (1st Cir.

1987), this Circuit noted the district judge’s significant

discretion over whether to hold evidentiary hearings by stating

that such hearings “cannot be convened at the whim of a suitor,

made available like popsicles in July, just because a passerby

would like to have one.” Id. at 44. Even if an objection to the

lack of an evidentiary hearing had been made, review of such a

decision would be narrow, looking only for an abuse of discretion.

United States v. Gerante, 891 F.2d 364, 367 (1st Cir. 1989).

Goodhue failed to object to the district court’s

application of the sentencing guidelines without an evidentiary

hearing as to the pure weight of the controlled substances. This

situation is directly controlled by United States v. Garcia, 954

F.2d 12 (1st Cir. 1992), where this Court held that an appellant

“effectively obviated the need for an evidentiary hearing” by

objecting to interpretations based upon facts instead of

challenging the underlying facts themselves. Id. at 19. In light

of the substantial deference given to a district court whether to
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hold such an evidentiary hearing and the failure of Goodhue to

request one, it is neither clear nor obvious that the district

court erred in applying the aggregate weight of the mixture

directly to the Sentencing Guidelines. See Donnelly, 370 F.3d at

95.

Goodhue’s second argument on appeal is that in the

absence of evidence of the pure weights of the controlled

substances, the district court erred by not applying instead

section 2D1.11 to 65.87 grams of red phosphorous. Appellant Br. at

18. Such application would have resulted in the lower Base Offense

Level of 24. Goodhue characterizes this argument as an issue of

law that turns on an interpretation of the Sentencing Guidelines.

See id. at 16. Even were we to assume that this is an issue of

interpretation, the unsettled nature of the law precludes a finding

of plain error. See Connelly, 351 F.3d at 546.

In response to the Methamphetamine Anti-Proliferation Act

of 2000,7 section 2D1.118 was amended to provide a new chemical

quantity table specifically for ephedrine and pseudoephedrine.

U.S. Sentencing Guidelines Manual § 2D1.11, app. C, amend. 611

(2004). One of the purposes behind this amendment was to reduce

the distinction between section 2D1.1, which concerns intent to

7
Pub. L. No. 106-310, 114 Stat. 1227 (2000) (codified in
scattered sections of the United States Code).
8
Section 2D1.11 is titled: “Unlawfully Distributing,
Importing, Exporting or Possessing a Listed Chemical; Attempt or
Conspiracy.”
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manufacture methamphetamine, and section 2D1.11, which addresses

attempt to manufacture methamphetamine from ephedrine,

pseudoephedrine, and phenylpropanolamine (“PPA”). Id. The

relationship between the two guideline sections is evidenced from

a cross reference in section 2D1.11 to section 2D1.1 that requires

the use of the Base Offense Level calculated under the latter

section if the offense involves the unlawful manufacture of a

controlled substance and the resulting offense level exceeds that

calculated under section 2D1.11. U.S. Sentencing Guidelines Manual

§ 2D1.11(c)(1) (2004).

The current section 2D1.11 calculates the Base Offense

Level by reference to an ephedrine, pseudoephedrine, and PPA drug

quantity table. Id. § 2D1.11(a), (d). To calculate the weight in

an offense that involves two or more precursor chemicals, the

section recommends the use of the aggregate weight of the

quantities of all such chemicals. Id. § 2D1.11 n.B.

This calculation, and thus the application of section

2D1.11, is straightforward where the weights of the pure precursor

chemicals are known. It becomes more difficult where the precursor

chemical is mixed with other substances that do not constitute

controlled substances. Section 2D1.11 does not directly address

the general issue of such mixtures. It does, however, address the

specific situation of a mixture in “tablet” form. Id. § 2D1.11

n.C. This section note states, “[i]n a case involving ephedrine,

pseudoephedrine, or phenylpropanolamine tablets, use the weight of
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the ephedrine, pseudoephedrine, or phenylpropanolamine contained in

the tablets, not the weight of the entire tablets, in calculating

the base offense level.” Id.9 In a tablet situation, therefore,

only the weight of the pure precursor chemicals is applied to the

drug quantity tables, not the total weight of the tablet itself.

See id.10

As the district court recognized, the tablet situation

differs from the general mixture situation because the percentage

of the controlled substance in a tablet is usually specifically

noted on the tablet package. See S. Tr. at 7:1-7. Thus, in a

tablet, there is typically no question as to the weight of the pure

precursor chemicals.

The district court did not face the clearly defined

tablet situation. Instead, it faced a more difficult situation --

9
A similar amendment -- Amendment 657 -- was made to section
2D1.1(c) for Oxycodone. Oxycodone is generally sold in pill
format. Prior to the amendment, the sentencing guidelines
established penalties for Oxycodone based on the weight of the
entire pill. Amendment 657 addressed the resulting proportionality
issues and modified the provision to weigh only the controlled
substance itself. See Carmen D. Hernandez, Amendments to the
United States Sentencing Guidelines--Part 1, Champion 18, 19-20
(March 2004).
10
The specific provision relating to tablets is the result of
an amendment that states: “[u]nlike ephedrine, which is purchased
from a chemical company and is virtually 100 percent pure, these
tablets contain a substantially lower percentage of ephedrine
(about 25 percent). To avoid unwarranted disparity, this amendment
adds a note to § 2D1.11 providing that the amount of actual
ephedrine contained in a pill is to be used in determining the
offense level.” U.S. Sentencing Guidelines Manual § 2D1.11, app.
C, amend. 519 (2004).
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applying section 2D1.11 to a mixture where the amounts of ephedrine

and pseudoephedrine had not been determined. This broader

question, though not directly addressed in section 2D1.11, is

directly addressed in section 2D1.1. U.S. Sentencing Guidelines

Manual § 2D1.1 n.A & cmt. n.1 (2004). Section 2D1.1 similarly

assigns a Base Offense Level by the application of the weight of

the controlled substance to a predetermined range. Note A of

section 2D1.1 states:

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 detectable amount of
the controlled substance. If a mixture or
substance contains more than one controlled
substance, the weight of the entire mixture or
substance is assigned to the controlled
substance that results in the greater offense
level.

The section further instructs that the weight of the entire mixture

ought not include “materials that must be separated from the

controlled substance before the controlled substance can be used.”

Id. § 2D1.1 cmt. n.1. If a mixture cannot be so separated, “the

court may use any reasonable method to approximate the weight of

the mixture of substance to be counted.” Id.

The district court identified and carefully considered

the inconsistency of using the aggregate weight of mixtures

containing undetermined amounts of ephedrine and pseudoephedrine

under section 2D1.11 in light of the tablet note’s exclusion of

substance weight not derived from a controlled substance. S. Tr.

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at 22:25-23:7. The district court addressed this situation by

applying three methods all derived from the starting point of 53.08

grams of mixture attributable to Goodhue. Id. at 22:8-24. The

court calculated the Base Offense Level by: 1) treating the mixture

as pure ephedrine and pseudoephedrine under section 2D1.11; 2)

cross-referencing to section 2D1.1 and calculating the equivalent

weight of marijuana; and 3) applying Goodhue’s yield analysis, and

then section 2D1.11 to the result. Id. Calculations under all

three methods resulted in a Base Offense Level of 28. Id. at 23:8-

13.

The district court navigated through this unguided and

unsettled territory by considering and ultimately adopting both

paths suggested by counsel and his own independent judgment that

calculating the marijuana equivalent under the cross-reference to

section 2D1.1 may be most appropriate given that section’s specific

guidance on such mixtures. As a result, it cannot be held that the

district court committed plain error by not interpreting section

2D1.11 as requiring the use of the weight of the red phosphorous as

a default.

2. Interpreting Section 2D1.11

Although the district court’s thoughtful, measured, and

reasonable interpretation of section 2D1.11 does not constitute

plain error, we go further to provide guidance to sentencing

courts.

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 We address the situation where the sentencing court has

before it a non-tablet mixture containing methamphetamine

precursors. Under section 2D1.11, the relevant drug weight for

sentencing purposes is the weight of the precursor chemicals

themselves. The burden is on the government to prove the weight of

the precursor chemicals to the district court. The initial

question ordinarily is whether the methamphetamine precursors

contained in such a non-tablet mixture may be isolated and

separately weighed. The burden is on the prosecution to show that

the isolation and weighing of the precursors is not feasible.

If the court finds that the process of isolating and

separately weighing the precursor components is not feasible, then

the district court may take guidance from Application Note 1 in

section 2D1.1. The court may apply any reasonable method to

approximate the undeterminable weight of ephedrine,

pseudoephedrine, or PPA from impure mixtures.

Where such a process is feasible, the government bears

the burden of proving the actual weight of the pure precursor

components. Cf. United States v. Ching Tang Lo, 447 F.3d 1212,

1222-23 (9th Cir. 2006) (demonstrating the ability of the

government to detail the percentage of ephedrine that existed in a

ma huang extract). The weight of the pure precursor components

will then be applied in aggregate directly to the drug quantity

charts in section 2D1.11.

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 If it is feasible to isolate and weigh the precursors and

the government has not done so, the government may well have failed

to meet its burden. We do not, however, exclude the possibility

that the non-precursor substances of the mixture are de minimis or

their weight is reasonably discernable by different means.

The court would also be warranted in considering whether

the government has engaged in affirmative misconduct in failing to

conduct the necessary test to isolate and measure. There is, we

stress, no claim of such misconduct here.11

As to 2D1.11(c)’s cross-reference to section 2D1.1,

Application Note 1 to section 2D1.1 makes clear that although the

district court should use the total weight of any mixture

containing a detectable amount of a controlled substance, U.S.

Sentencing Guidelines Manual § 2D1.1 n.A (2004), the appropriate

drug weight for sentencing purposes excludes “materials that must

be separated from the controlled substance before the controlled

substance can be used.” As a result, the burden is on the

government to demonstrate that no part of a mixture is a substance

that must be separated before the substance may be used. If the

mixture does contain such substances, and they can be separated,

the government has the burden of proving the actual weight of the

11
The prosecution informed us at oral argument that it is
atypical for the district court to be faced with a mixture
containing methamphetamine precursors that have not been isolated
and weighed. This situation, the government represented, arose
because a state government crime lab performed the chemical
analysis before the case was referred for federal prosecution.
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usable part of the mixture. If the non-usable substances cannot be

segregated, the court may make a reasonable approximation of the

usable substances, as provided in Application Note 1.

III. Conclusion

In sum, we conclude that Goodhue’s arguments as to the

district court’s errors in calculating his Base Offense Level fail

to satisfy plain error review. We therefore remand this case for

the limited purpose of recalculating the sentence under the correct

Criminal History Category. Upon remand, the district court may

reconsider the entire sentence in light of this opinion.

The decision of the district court is vacated and the

case remanded for resentencing.

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