US v. Giggey

Filing

OPINION issued by William J. Kayatta , Jr., Appellate Judge; Bruce M. Selya, Appellate Judge and David J. Barron, Appellate Judge. Published. [16-2391]

Case: 16-2391

Document: 00117189055

Page: 1

Date Filed: 08/14/2017

Entry ID: 6112851

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

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SELYA, Circuit Judge.

Date Filed: 08/14/2017

Entry ID: 6112851

Controlled substances continue to

cast a dark shadow over a large segment of American society.
situation

is

permutations
colloquially

made
of
known

even
such
as

worse

by

substances.
bath

salts,

the

proliferation
Synthetic

represent

one

of

That
new

cathinones,
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.
I.

Discerning no clear error, we affirm.

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

disposition hearing.

Page: 3

report,

Date Filed: 08/14/2017

and

the

Entry ID: 6112851

transcript

of

the

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

incriminating text messages.

telephone

replete

with

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

841(a)(1), 846.

analogue

substances.

See

21

U.S.C.

§§

813,

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

March

until

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. 320713, 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
U.S.C. § 802(32)(A).

See 21

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.

1

Schedule 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 alphaPVP

than

methcathinone

comparator.

and,

therefore,

was

the

appropriate

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.
97-121 months.

These subsidiary findings yielded a GSR of

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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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

mari[j]uana."

into

its

"equivalent

quantity

of

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

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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.
§2D1.1, cmt. n.6; see Hurley, 842 F.3d at 171-72.
which

drug

considered.

is

most

closely

related,

three

USSG

To determine

factors

must

be

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.
In

the

case

at

See id. §2D1.1(c) & cmt. nn.6 & 8.
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

more

the

court

closely

erred

related

to

in

finding

that

alpha-PVP

than

methcathinone

was

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 alphaPVP 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
alpha-PVP.

in

the

search

for

a

suitable

comparator

to

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

2017).

Cir.

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.
Walker, 665 F.3d at 232.

See, e.g.,

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.
methodically

subjected

the

two

proposed

The court

comparators

— methcathinone and pyrovalerone — to the prescribed tripartite
test:

it

inspected

and

contrasted

the

chemical

pharmacological effect, and potency of each drug.

structure,

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

methcathinone

and

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analysis,

the

pyrovalerone

Date Filed: 08/14/2017

court
were

determined

Entry ID: 6112851

that

substantially

both

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

pharmacological effect to alpha-PVP.

substantially

similar

in

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

6

This 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."
2016).

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United States v. Jordan, 813 F.3d 442, 447 (1st Cir.

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

substantially similar pharmacological effect and potency.

of
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."

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Coombs,

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857 F.3d at 452.

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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

pyrovalerone

factual
would

be

challenge
a

better

hinges
choice

on
as

the
a

notion

that

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.
hopeless.

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This argument is

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"The

rule

of

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lenity

Date Filed: 08/14/2017

generally

applies

to

Entry ID: 6112851

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 alphaPVP 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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