Court Opinion

ID: 4195626
Source: CourtListenerOpinion
Date Created: 2017-08-14 19:00:37.942152+00
Date Added: 2024-06-11T09:37:37.281959
License: Public Domain

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

                                    - 5 -
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

                                 - 10 -
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

                                       - 11 -
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).

                                  - 13 -
           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."

                                      - 14 -
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,

                                        - 15 -
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.

                                       - 16 -
            "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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