United States v. Giggey

United States Court of Appeals
For the First Circuit
No. 16-2391
UNITED STATES OF AMERICA,
Appellee,
v.
LEDA GIGGEY,
Defendant, Appellant.
APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF MAINE
[Hon. John A. Woodcock, Jr., U.S. District Judge]
Before
Kayatta, Selya and Barron,
Circuit Judges.
Matthew S. Erickson on brief for appellant.
Richard W. Murphy, Acting United States Attorney, Renée M.
Bunker, Assistant United States Attorney, Appellate Chief, and
Benjamin M. Block, Assistant United States Attorney, on brief for
appellee.
August 14, 2017
SELYA, Circuit Judge. Controlled substances continue to
cast a dark shadow over a large segment of American society. That
situation is made even worse by the proliferation of new
permutations of such substances. Synthetic cathinones,
colloquially known as bath salts, represent one of these
permutations, and we recently had occasion to warn that their
illegal use was becoming a mounting problem in the District of
Maine. See United States v. Coombs, 857 F.3d 439, 443 & n.1 (1st
Cir. 2017).
When drug offenses involve drugs not listed in the
relevant tables incorporated in the sentencing guidelines, those
drugs are converted into their marijuana equivalent for sentencing
purposes. See USSG §2D1.1, cmt. nn.6 & 8. This appeal requires
us, for the first time, to pass upon the method and manner in which
that conversion is effected with respect to synthetic cathinones.
The court below used a conversion metric grounded in its finding
that methcathinone is the drug referenced in the sentencing
guidelines that is most closely related to the synthetic cathinone
alpha-pyrrolidinopentiophenone (alpha-PVP). Using this metric,
the court sentenced defendant-appellant Leda Giggey to a 72-month
term of immurement. Discerning no clear error, we affirm.
I. BACKGROUND
We briefly rehearse the facts and travel of the case,
drawing upon the plea agreement, the uncontested portions of the
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presentence investigation report, and the transcript of the
disposition hearing. See United States v. Del Valle-Rodríguez,
761 F.3d 171, 173 (1st Cir. 2014); United States v. Dietz, 950
F.2d 50, 51 (1st Cir. 1991). Between 2012 and 2015, the defendant
procured 2,120.75 grams — more than 21,000 individual doses — of
synthetic cathinones, some from local suppliers and some from
China. During this period, she became one of the foremost dealers
of bath salts in Aroostock County, Maine. After some time had
gone by, law enforcement officers threw a monkey wrench into her
drug-distribution business: they executed a search warrant at her
residence and found 1.07 grams of alpha-PVP, a drug ledger, two
digital scales, and a cellular telephone replete with
incriminating text messages. The defendant's arrest followed
apace.
In due course, the defendant pleaded guilty to
conspiracy to distribute and possession with intent to distribute
controlled and analogue substances. See 21 U.S.C. §§ 813,
841(a)(1), 846. Federal drug laws classify proscribed drugs in
five separate schedules, which are updated on an annual basis.
See id. § 812(a). Because alpha-PVP was not listed on any of these
schedules until March of 2014, see Schedules of Controlled
Substances: Temporary Placement of 10 Synthetic Cathinones into
Schedule I, 79 Fed. Reg. 12,938, 12,941 (Mar. 7, 2014) (codified
at 21 C.F.R. § 1308.11), the government prosecuted the defendant
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under the Controlled Substance Analogue Enforcement Act of 1986
(Analogue Act), Pub. L. No. 99-570, §§ 1201-1204, 100 Stat. 3207-
13, 3207-13 to -14 (codified at 21 U.S.C. §§ 802(32), 813). The
Analogue Act facilitates the regulation of new drugs which, though
not currently outlawed, exhibit substantial similarities to a
controlled substance found in either Schedule I or II.1 See 21
U.S.C. § 802(32)(A). The Analogue Act defines a "controlled
substance analogue" as:
[A] substance (i) the chemical structure of
which is substantially similar to the chemical
structure of a controlled substance in
schedule I or II; (ii) which has a stimulant,
depressant, or hallucinogenic effect on the
central nervous system that is substantially
similar to or greater than the stimulant,
depressant, or hallucinogenic effect on the
central nervous system of a controlled
substance in schedule I or II; or (iii) with
respect to a particular person, which such
person represents or intends to have a
stimulant, depressant, or hallucinogenic
effect on the central nervous system that is
substantially similar to or greater than the
stimulant, depressant, or hallucinogenic
effect on the central nervous system of a
controlled substance in schedule I or II.
Id.
1Schedule I is reserved for drugs with "no currently accepted
medical use." 21 U.S.C. § 812(b)(1). Schedule II covers drugs
which, although they may have an accepted medical use, are such
that "[a]buse of the drug . . . may lead to severe psychological
or physical dependence." Id. § 812(b)(2). Schedules III, IV, and
V cover drugs of decreasing levels of potential abuse and
dependence. See id. § 812(b)(3)-(5).
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Drug quantity is an important integer in the sentencing
calculus for most controlled substance offenses. See United States
v. Dunston, 851 F.3d 91, 94 (1st Cir. 2017). The sentencing
guidelines implement this concept through, inter alia, the use of
a Drug Quantity Table, see USSG §2D1.1(c), and Drug Equivalency
Tables, see id. §2D1.1, cmt. n.8(D).
As a practical matter, less commonly used drugs and new
drugs are frequently not referenced in these tables. In such
cases, the drug must be converted into the marijuana equivalent
quantity of the most closely related controlled substance listed
in the guidelines. Here, the government argued that methcathinone
(a Schedule I controlled substance) was the appropriate comparator
for alpha-PVP. The defendant countered that pyrovalerone (a
Schedule V controlled substance) was more closely related to alpha-
PVP than methcathinone and, therefore, was the appropriate
comparator. The defendant's sentence turned, to a large extent,
on the outcome of this dispute: if methcathinone was deemed to be
the proper comparator, the defendant's guideline sentencing range
(GSR) promised to be appreciably higher.
The district court convened the disposition hearing on
November 8, 2016. Drug quantity was hotly contested in motion
papers filed prior to the hearing. As matters turned out, the
district court had confronted this same quandary in an earlier
case. See United States v. Brewer, No. 1:15-cr-00003, 2016 WL
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3580614 (D. Me. June 28, 2016). Rather than reinventing the wheel,
the court opted to incorporate by reference its previous analysis,
which found methcathinone to be the most closely related controlled
substance to alpha-PVP for sentencing purposes.2 On that basis,
the court found the defendant responsible for the equivalent of
805.89 kilograms of marijuana.3
With this finding as the linchpin, the court made certain
offense-level adjustments (not relevant here), calculated the
defendant's total offense level (30), and placed her in criminal
history category I. These subsidiary findings yielded a GSR of
97-121 months. After considering the factors limned in 18 U.S.C.
§ 3553(a), the court imposed a downwardly variant sentence of 72
months' imprisonment. This timely appeal ensued.4
2 Neither party has objected to the district court's reliance
upon Brewer, and the defendant has raised no arguments other than
those raised in Brewer. Because the district court relied on
Brewer without making any new findings or adding any new analysis,
our references to the district court's decision in this case
necessarily refer to its findings and analysis in Brewer.
3 The court also found the defendant responsible for an
additional drug quantity after converting certain opioids into
their marijuana equivalent. This incremental increase in overall
drug quantity has no bearing on the issues before us.
4 The plea agreement contains a waiver of the defendant's
right to appeal from any sentence of 57 months or less. Given the
length of the sentence imposed, this waiver has no effect on the
defendant's appeal.
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II. ANALYSIS
At the outset, we pause to review the methodology used
to determine drug quantity for crimes involving prohibited drugs
not specifically referenced in the sentencing guidelines. To
begin, the guidelines provide a series of base offense levels for
controlled substance offenses. See USSG §2D1.1. The most common
controlled substances (for example, heroin, cocaine, marijuana,
and the like) appear in the Drug Quantity Table, which specifies
particular base offense levels depending upon the drug type and
quantity involved in a given offense. See id. §2D1.1(c). Many
less common drugs are assigned ratios in the Drug Equivalency
Tables, which permit conversion of a given quantity of any of these
controlled substances into its "equivalent quantity of
mari[j]uana." Id. §2D1.1, cmt. n.8(A)(i); see United States v.
Demers, 842 F.3d 8, 12 (1st Cir. 2016). In such instances,
sentencing courts "[u]se the offense level that corresponds to the
equivalent quantity of mari[j]uana [in the Drug Quantity Table] as
the base offense level for the [actual drug] involved in the
offense." USSG §2D1.1, cmt. n.8(A)(iii); see United States v.
Hurley, 842 F.3d 170, 171-72 (1st Cir. 2016).
Although the Drug Quantity Table and the Drug
Equivalency Tables together cover a broad array of controlled
substances, these tables do not exhaust the universe of prohibited
drugs. When either a controlled substance or a controlled
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substance analogue does not appear in either of the tables, the
sentencing court must calculate the offender's base offense level
using the marijuana equivalent of "the most closely related
controlled substance" that is referenced in the tables. USSG
§2D1.1, cmt. n.6; see Hurley, 842 F.3d at 171-72. To determine
which drug is most closely related, three factors must be
considered. They include
(1) whether the unreferenced controlled
substance has a chemical structure that is
substantially similar to a controlled
substance referenced in the guidelines;
(2) whether the unreferenced controlled
substance has a stimulant, depressant, or
hallucinogenic effect on the central nervous
system that is substantially similar to the
stimulant, depressant, or hallucinogenic
effect of a controlled substance referenced in
the guidelines;
(3) whether a lesser or greater quantity of
the unreferenced controlled substance is
needed to produce a substantially similar
effect on the central nervous system as a
controlled substance referenced in the
guidelines.
See USSG §2D1.1, cmt. n.6.
Once the proper comparator has been identified, the
court calculates the unreferenced drug's marijuana equivalent
using the marijuana equivalent value assigned to the comparator in
the Drug Equivalency Tables. See id. §2D1.1, cmt. nn.6 & 8. The
offender's base offense level is then established by comparing
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this deduced marijuana equivalent quantity to the appropriate tier
in the Drug Quantity Table. See id. §2D1.1(c) & cmt. nn.6 & 8.
In the case at hand, the defendant challenges the
district court's selection of methcathinone as the appropriate
comparator for alpha-PVP on two distinct grounds. First, she
asserts that the district court erred by restricting its search
for a comparator drug to Schedule I and II controlled substances.
Second, she asserts that the court erred in finding that
methcathinone was more closely related to alpha-PVP than
pyrovalerone. We evaluate these claims of error separately.
A.
The defendant's first claim of error posits that the
sentencing court impermissibly limited its search for an alpha-
PVP comparator to the universe of Schedule I and II controlled
substances. As a result, the defendant says, the court excluded
her preferred comparator, pyrovalerone, which is a Schedule V
controlled substance. This amounts to a challenge to the district
court's application of the sentencing guidelines, and we review
the sentencing "court's interpretation and application of the
sentencing guidelines de novo." United States v. Walker, 665 F.3d
212, 232 (1st Cir. 2011).
In this case, the district court, adopting its findings
in Brewer, 2016 WL 3580614, at *11, concluded that, as a matter of
law, only a Schedule I or Schedule II controlled substance can be
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considered the most closely related drug to a controlled substance
analogue not referenced in the sentencing guidelines. The plain
language of the sentencing guidelines supports the conclusion that
an analogue comparator must be a controlled substance selected
from either Schedule I or II. The commentary to the relevant
sentencing guideline states, in an application note, that "[f]or
purposes of this guideline 'analogue' has the meaning given the
term 'controlled substance analogue' in 21 U.S.C. § 802(32)." USSG
§2D1.1, cmt. n.6. The statute, in turn, defines a controlled
substance analogue as a substance that is "substantially similar"
in chemical structure, pharmacological effect, and intended effect
to "a controlled substance in schedule I or II." 21 U.S.C.
§ 802(32)(A) (emphasis added); see McFadden v. United States, 135
S. Ct. 2298, 2303-05 (2015).
It is a familiar tenet that the text of a statute
"furnishes the most reliable guide to its interpretation." United
States v. Suárez-Gonzáles, 760 F.3d 96, 99 (1st Cir. 2014). The
same respect is accorded to the text of the sentencing guidelines.
See id. Here, the plain language of both the statute and the
application note indicate that the proper comparator for an
unreferenced controlled substance analogue must be drawn from
Schedule I or II. See 21 U.S.C. § 802(32)(A); USSG §2D1.1, cmt.
n.6; see also United States v. Emerson, No. 2:15-cr-17, 2016 WL
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1047006, at *5 (D. Vt. Mar. 10, 2016) (terming any other result
"absurd").
But there is more to the story. Here, the district court
— after stating that the controlled substance analogue must be
chosen from the ranks of Schedules I and II — prudently assumed,
favorably to the defendant, that pyrovalerone (the Schedule V
controlled substance identified by the defendant) was eligible for
consideration in the search for a suitable comparator to
alpha-PVP. The court then proceeded to examine both methcathinone
(the Schedule I controlled substance identified by the government)
and pyrovalerone in order to determine which drug was most closely
related to alpha-PVP. It was only after this detailed examination
of the competing candidates proposed by the parties that the court
concluded that methcathinone was the proper comparator.
That ends this aspect of the matter. As we recently
explained, "courts should not rush to decide unsettled issues when
the exigencies of a particular case do not require such definitive
measures." Privitera v. Curran (In re Curran), 855 F.3d 19, 22
(1st Cir. 2017). So it is here: the sentencing court's
prophylactic approach obviates the need for us to make a definitive
holding as to whether the proper comparator for a controlled
substance analogue can be chosen only from the possibilities
presented by Schedules I and II. Because the sentencing court
went the extra mile and thoroughly considered the Schedule V drug
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proposed by the defendant in its search for the proper comparator,
it would be gratuitous to decide whether the court's search should
have been limited to Schedules I and II. Given the breadth of the
inquiry actually undertaken by the court, any error in stating
that the search should be restricted to Schedules I and II was
manifestly harmless. See, e.g., United States v. Alphas, 785 F.3d
775, 780 (1st Cir. 2015) (explaining that "an appellate court may
deem such an [alleged] error harmless if, after reviewing the
entire record, it is sure that the error did not affect the
sentence imposed").
B.
This brings us to the defendant's plaint that the
sentencing court erred in determining that methcathinone was the
controlled substance referenced in the sentencing guidelines that
corresponds most closely to alpha-PVP. Typically, findings of
fact at sentencing are reviewed for clear error. See, e.g.,
Walker, 665 F.3d at 232. It is an open question in this circuit,
though, whether a district court's selection of the most closely
related controlled substance is a factual or a legal determination.
Withal, we do not write on a pristine page. Several of
our sister circuits have held that such a determination is a
factual matter and, thus, engenders review only for clear error.
See, e.g., United States v. Novak, 841 F.3d 721, 730 (7th Cir.
2016); United States v. Malone, 828 F.3d 331, 337 (5th Cir. 2016);
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United States v. Ramos, 814 F.3d 910, 918 (8th Cir. 2016); United
States v. Chowdhury, 639 F.3d 583, 585-86 (2d Cir. 2011) (per
curiam). We share this view, and we proceed to assay the district
court's "comparator" finding for clear error.5 That standard of
review is deferential: it requires that we accept findings of fact
and inferences drawn therefrom unless, "on the whole of the record,
we form a strong, unyielding belief that a mistake has been made."
Demers, 842 F.3d at 12 (quoting Cumpiano v. Banco Santander P.R.,
902 F.2d 148, 152 (1st Cir. 1990)).
Here, the district court did not clearly err. The court
methodically subjected the two proposed comparators
— methcathinone and pyrovalerone — to the prescribed tripartite
test: it inspected and contrasted the chemical structure,
pharmacological effect, and potency of each drug. What is more,
the court painstakingly conducted this inquiry through the prism
of competing expert testimony and evidentiary proffers purporting
to show which drug should be deemed more closely related to
alpha-PVP.
5 While we review the district court's factfinding on the
designated factors only for clear error, we reserve the right, in
an appropriate case, to review the net result of that combined
factfinding on a less deferential standard. Cf. Ornelas v. United
States, 517 U.S. 690, 691, 699 (1996) (explaining that factual
findings underlying probable cause determinations are reviewed for
clear error but determination of "ultimate question[]" as to
whether probable cause exists is reviewed de novo).
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In its analysis, the court determined that both
methcathinone and pyrovalerone were substantially similar in
chemical structure to alpha-PVP (even though pyrovalerone was
somewhat "more similar . . . in its chemical structure"). The
court next determined, based principally on the proffered expert
testimony, that both drugs were substantially similar in
pharmacological effect to alpha-PVP. Last — but far from least —
the court determined that methcathinone more closely resembled
alpha-PVP in potency. In this regard, the court stated that
"[a]lpha-PVP is more potent than methamphetamine, and thus is at
least as potent as methcathinone."6 The court found that the
defendant had not proven pyrovalerone to be as potent.
After a thorough review of the record, we conclude that
the district court did not clearly err in finding that
methcathinone is the drug referenced in the sentencing guidelines
that is most closely related to alpha-PVP. The district court
found the government's expert evidence more persuasive, and we
have said that "[w]hen dueling experts have each rendered a
coherent and facially plausible opinion, the trial court's
decision to adopt one and reject the other cannot be clearly
6This finding is of a piece with the defendant's admission
at sentencing that alpha-PVP "is a powerful, highly addictive
poisonous chemical that left me with a mind riddled with poor
judgment."
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erroneous." United States v. Jordan, 813 F.3d 442, 447 (1st Cir.
2016). That is precisely the situation here.
In an effort to undermine the district court's
factfinding, the defendant emphasizes that pyrovalerone was found
to be closer in chemical structure. This emphasis, however,
ignores the district court's supportable findings regarding the
two remaining guideline factors. When all is said and done, a
sentencing court is not obliged "to match substances under each of
the factors." Chowdhury, 639 F.3d at 586. So, for example, a
substance that is not the best fit in terms of chemical structure
may still be the most appropriate comparator because of
substantially similar pharmacological effect and potency. See
Novak, 841 F.3d at 730.
In this instance, the district court, after taking each
of the three prongs of the test into consideration, found that, on
the whole, methcathinone was the most closely related controlled
substance to alpha-PVP. Pertinently, the district court gave
significant weight to potency, finding that alpha-PVP packed a
punch comparable to methcathinone, and that there was no proof
that pyrovalerone was as powerful. Put simply, the court's
rationale rests heavily (and logically) on the similarity in
potency between methcathinone and alpha-PVP. The plausibility of
this rationale is not weakened simply because the court "did not
weigh the factors as the [defendant] would have liked." Coombs,
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857 F.3d at 452. The short of it is that the court's careful
calibration of the decisional scales gives us confidence that its
analysis was not clearly erroneous. See United States v. Platte,
577 F.3d 387, 394 (1st Cir. 2009) (finding no clear error when
drug quantity determination was "supported by a sensible (though
not inevitable) view of the record").
In all events, the defendant's argument fails on its own
terms. Her factual challenge hinges on the notion that
pyrovalerone would be a better choice as a comparator than
methcathinone, not that methcathinone is an implausible choice (a
point the defendant freely concedes when she states, in her
appellate brief, that "there is ample evidence on the record to
support the sentencing [c]ourt's finding"). This approach runs
headlong into the settled rule that "where there is more than one
plausible view of the circumstances, the sentencing court's choice
among supportable alternatives cannot be clearly erroneous."
United States v. Ruiz, 905 F.2d 499, 508 (1st Cir. 1990).
In a last-ditch effort to turn the tables, the defendant
invokes the rule of lenity. She argues that because both
methcathinone and pyrovalerone could be recognized as comparators,
we should mandate the use of the latter because doing so will
result in a markedly diminished sentence. This argument is
hopeless.
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"The rule of lenity generally applies to criminal
statutes that are subject to more than one plausible interpretation
and demands that the interpretation more favorable to the defendant
prevail." Suárez-Gonzáles, 760 F.3d at 101. When statutory
ambiguity is wholly absent, any "concerns that may be redressed
through an application of the rule of lenity" are also absent.
United States v. Aponte-Guzmán, 696 F.3d 157, 160 (1st Cir. 2012);
see Suárez-González, 760 F.3d at 101. Here, the defendant advances
no claim of statutory ambiguity but, rather, merely reprises her
factbound claim that pyrovalerone is a better comparator to alpha-
PVP than methcathinone. Seen in this light, the defendant's
attempt to embrace the rule of lenity necessarily fails.
III. CONCLUSION
We need go no further. For the reasons elucidated above,
the sentence is
Affirmed.
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