F OR P UBLICATION



### UNIT E D ST AT E S CO URT O F APPE AL S FO R T H E NINT H CIRCUIT

U N I T E D S T A T E S O F A M E R I C A , Plaintiff-Appellee
,

v

.

M A T T H E W S T E W

A R T , Defendant-Appellant

. N o. 13-10048

D.C. No. 2:10-cr-00564- L DG-VCF

- 1

OPI NI ON

A ppeal from the United States District Court for the District of Nevada L loy d D. Georg e, District J udg e , Presiding

Arg ued and Submitted March 11, 2014—San F rancisco, California

F iled J uly 31, 2014

B efore: Sidney

R. Thomas, Ray

mond C. F isher and Marsha S. B erz on, Circuit J udg es.

O pinion by

J udg e F isherU N I T E D S T A T E S V

. S T E W A R T 2

SUMMARY *

Crim inal Law

Affirming a sentence for distributing a controlle d substance, the panel r eaffirmed t h is court’s holding that because 18 U.S.C. § 944(h) does no t l imit career offender
status under the Sentencing Guidelines to defendants with
t w o p r e d i c a t e f

e d e r a l c o n v i c t i o n s , t h e S e n t en c i n g Commission d id not ex ceed the scop e o f its deleg ated authority by including p rior state convictions as an additional basis for career offender status.

The panel also held that the distr i c t court was mistaken about the impact of the purity of the controlled substance, but that the defendant’s sentence was noneth e l ess reasonable under the totality

of the circumstances.

COUNSEL

J eremy M. D e l icino, Salt L ake City
, Utah, for D efendantAppellant.

Peter S. L evitt ( arg ued), A ssistant U nited States Attorney
, Eliz abeth O. W hite, A ppellate Chief, Daniel G. B og den, Unite d S tates Attorney
, L as Veg as, Nevada, for PlaintiffAppellee.

* T h is su m m ary co n stitu

tes n o part o f th e o p in io n o f th e co u rt. It h as b een p rep ared b y

co u rt staf

f f o r th e co n v en i en ce o f

th e read er.U N I T E D S T A T E S V

. S T E W A R T 3

OP INION

F I SHER, Circuit J udg e :

Matthew Stewart pled g u ilty to two c ounts of distributing a controlled substance in violation of 21 U.S.C. § 841(a)(1). Be cause he h ad two p rior state felony convictions fo r contro l l e d s u

b s tance o ffenses, the district court sentenced him

as a career offender. See United States Sentencing Guidelines Manual ( U.S.S.G.) § § 4B 1.1, 4B 1.2. Stewart appeals his sentence, arg u ing that the Sentencing Commission ex ceeded its statutory authority under 28 U.S.C. § 994(h) by including
state convic t ions as predicate o ffenses for purposes o f defining a career offender. H e further contends his sentence is substantively

unreasonable b ecause of the very low purity of the controlled substance h e sold and the career o f f e n d e r g uidelines’ over-representation o f his criminal history

. W e

once ag ain hold that the Commission’s career o f f ender
g uidelines are a permissible interpretatio n o f the relevant
statutes. See United States v. Rivera
, 99 6 F .2d 993, 994–97 (9th Cir. 1993). W e further conclude th a t the district court

was mistaken about the impact of the purity of the controlled substance, but that S t ewart’s sentence w as nonetheless reasonable u n der the totality of the c ircumstances. W e therefore affirm.

I

I n J uly 2010, federal Drug Enforcement A g ency (DEA) officers learned from a confidential source that Ste w art was potentially a “ g allon producer” and d istributor of ga mmahy drox y buty ric acid (GHB ). Acting on this tip, the DEA initiated a series of con t r o lled buy s of GHB from Stewart. On three separate occasions over the nex t several mon t h s,U N I T E D S T A T E S V

. S T E W A R T 4

Stewart sold water b o t tles – each containing a detectable
amount of GHB dissolved in water – to an undercover officer:

a sing le w ater bottle f

or $ 160; eig ht water bottles for $1,700; and 16 water bottles c ontaining approx imately two g allons o f total liquid for an unkno wn price. Ag e nts arrested Stewart and conducted a search o f h is residence, where they s e i z e d additional water bottles containing liquid with a detectable
amount of GHB

. L aboratory testing on all o f the seiz ed bottles confi rmed the presence of GHB in 11,359 milliliters of total liquid, or about three g allons.

Stewart pled g uilty to two counts o f distributing a controlled substance u n d e r 21 U.S.C § 841(a)(1). Absent application o f the c areer offender g u idelines, Stewart would have h ad a criminal history c ateg o r y o f I I I

. B u t because Stewart had two prior state f e l ony convictions for d

rug distribution, he qualified as a c ar e e r offender w ith an automatic criminal history categ ory o f VI

. See U.S.S.G. § 4B 1 .1(a)–(b). Stewart’s first c onviction was for the sale o f ecstasy tablets in 2002, and his second w a s f o r the sale o f cocaine in 2 005. B ased on the 20-y ear statut o r y max imum
term of imprisonment f

or the offense t o which Stewart p led
g uilty
, 21 U.S.C. § 841(b)(1)(C), the career offender
g uidelines r eset Stewa r t ’ s offense level to 3 2, see U.S.S.G. § 4B 1.1(b)(3). Apply ing a crimin a l h istory categ ory o f VI and a three-level down w a r d a djustment for acceptance o f responsibility
, the district court c alculated a g uidelines r ang e of 151 to 1 88 months of imprisonment. Althoug h the district
court fou nd that a sentence within this rang e would be appropriate, it nonetheless sentenced Stewart to 120 months’ imprisonment. Stewart timely appealed his sentence.U N I T E D S T A T E S V

. S T E W A R T 5

II

The Sentencing Commission’s authority for t he career offender g u idelines rests on 28 U.S.C. § 994. Section 994(h) directs the Commission to “assure” that the g uidelines specify

a sentence “at or near” the statutory max imum for a defendant who: (1) has been c onvicted o f a crime of violence or a controlled substance offense; a nd (2) has two or more prior felony convictions, each of which is a crime of violence or a controlled substance offense. See 28 U.S.C. § 994(h).

Carry ing o ut this mandate, the Commission promulg ated the career o ffender g uidelines, w h ich categ oriz e an adult defendant as a “career offender” when the d e f endant (1) is convicted of “a f

elony that is either a crime of violence or a controlled substance offense” a n d (2) “has at least two prior felony convictions of either a crime of violence or a controlled substance offense.” U.S.S.G. § 4B 1.1(a); see also United States v. M

itchell
, 624 F

. 3d 102 3
, 1 0 26 (9th Cir. 2010). Th e gu i delines define a “controlled substance offense” as “an offense under federal or stat e law” that “prohibits the manufacture, impo r t, ex port, distribution, o r dispensing o f a controlled substance,” or p ossession of a controlled substance with the intent to do the same. U.S.S.G. § 4B 1.2(b).

Stewart a cknowledg es that he was properly c ateg oriz ed a s

a c a reer offender under the g uidelines, b ased on his federal conviction for distributing GHB and his two prior state d rug distribution convictions. See U.S.S.G. § § 4B 1.1, 4B 1 .2. He
arg ues, however, th a t the career o ffender g uidelines a re invalid because they conflict with the plain lang uag e o f § 9 94(h), which he interprets as requiring a g uidelines
sentence a t o r near the statutory max imum only forU N I T E D S T A T E S V

. S T E W A R T 6

defendants with two prior federal , not state, drug trafficking convictions. His arg ument relies on the lang uag e of § 994(h), which specifies career offender treatment only f or a defendant who has two or more pre v i o u s c onvictions for a controlled substance offense “ descri b e d in” certain federal controlled substances statutes:

The Co m m ission shall a ssure that the guidelines specify a sentence to a term o f imprisonment at or near the max i m um term authoriz ed for categ o ries of defendants in which the d efendant is e ig hteen y ears old o r older and –

(1) has been convicted of a felony that is –

(A) a crime of violence; or

(B ) an offense described in section 401 o f the Controlled Substances Act (21 U.S.C. 841), sections 1002(a), 1005, and 1009 o f the Controlled Substances I mport a nd Ex port Act (21 U. S

. C

. 952(a), 955, a nd 959), and chapter 705 of title 46; and

(2) has previously been convicted of two o r more prior felonies, each of which is –

(A) a crime of violence; or

(B ) an offense described in section 401 o f the Controlled Substances Act (21 U.S.C. 841), sections 1002(a), 1005, and 1009 o f the Controlled Substances I mport a ndU N I T E D S T A T E S V

. S T E W A R T 7

Ex port Act (21 U.S.C. 952(a), 955
, and 959), and chapter 705 of title 46.

28 U.S.C. § 994(h). On the streng th o f this lang uag e, Stewart
arg ues that the Commissi o n ex ceeded its authority when it adopted g u idelines imposing career offender status for previous state controlled substance convictions.

W e rejected this very a

r g ument in United States v. Rivera
, 996 F .2d 993, 994–97 (9th Cir

. 1 9 93), a nd we now reaffirm Rivera ’s c ontinuing validity

. I n Rivera
, we h el d t h at the
g uidelines were a “ sufficiently reasonable ” i nterpretation o f
t h e a mbig uous lang u a g e of § 994(h), because this section is
not limited to p r e d i c a te offenses under federal law but

ex tends to conduct involving controlled substances that could ha v e been charg ed federally

. See id. W e further noted that the career offender g uidelines w ere consistent with Cong ress’ intent to punish repeat drug traffickers reg ardless of whether
t h e i r p r edicate convictions were state or federal. See id. at 996.

Stewart arg ues that Rivera cannot be reconciled with the Supreme Court’s subsequent decision in United States v

. LaBonte
, 5 20 U.S. 751 (1997), because Rivera applied an

erroneous standard of review. W e do n ot ag ree that LaBonte undermines Rivera ’s holding

. LaBonte held that the Commission’s definition of “offense statutory max imum” in § 4B 1.1 was invalid because it wa s “at odds with the plain lang uag e” and “ordinary meaning ” of 2 8 U

. S .C. § 994(h). 520 U.S. at 756, 7 5 7 ( quoting Moskal v. United States
, 498 U.S. 103, 108 ( 1990)) (internal quotation marks omitted). The Court noted that “Cong r ess has dele ga t ed to the Co m mission ‘sig nificant discretion in formulating ’” the sentencing g uidelines, but the Commission’s promulg at i o nsU N I T E D S T A T E S V

. S T E W A R T 8

must nonetheless “bow to the specific direct i v es o f Cong r ess.” Id. a t 757 (quoting Mi s t r e tta v. U nited States
, 488 U .S. 361, 377 (1989)); see also U nited States v. Tercero
, 734 F .3d 979, 982 (9th Cir. 2013) (ex plaining that LaB o nte invalidated a g uidelines provision as being “in direct conflict” with the authoriz ing statute).

Admittedly
, we applied a different standard of review in Rivera
, asking “whether the Sen t encing Guideline [was]

‘ sufficiently reasonable’ in lig ht of the cong ressio n al directive to the Commission,” 996 F .2d at 994, r at h e r than whether there was a direct conflict with the s tatute. Nevertheless, our inquiry was consistent with the analy sis applied in LaBonte because a g uid eline that constitutes a “sufficient l y reasonable” interpretation of the enabling statute cannot be in direct conflict with the statute’s plain mandate.

I n Rivera
, w e first found § 994(h) to be ambig uous, because “it is not a t all clear that C o ng ress intended to exclude state [ controlled substance] c onvictions” as predicate offenses trig g ering c a

reer offender status. 9 9 6 F .2d at 995–96. O nly then d id w e conclude that the Comm i s s i o n ’s interpretation was a sufficien t ly r easonable implementation of cong ressional intent. See id

. Althoug h § 9 94(h) could be interpreted as St ewart prefers – that career offender status does not d e pend on prior state f e lony convictions – there is no direct conflict between the Commission’s c o n t r a ry interpretation and section 9 94(h)’s plain lang uag e. S ee id. at 995; see also United States v. Beasley
, 12 F .3d 280, 283 (1st Cir. 1993) (holding that a “literal reading ” of this section
suppor ts the Commission’s interpretation); United States v

. W hyte , 892 F .2d 1170, 1174 (3d Cir. 1 989) (holding that the Commission’s interpretation “is a utho r i z e d, if not required, by section 9 94(h)”). Because Rivera is n ot “ clearlyU N I T E D S T A T E S V

. S T E W A R T 9

irreconcilable with the reasoning or t h e o r y ” of LaBonte
, we remain bound by its holding

. Miller v. Gamm i e , 3 3 5 F .3d 889, 893 (9th Cir. 2003) (en banc). 1

Even if we were f

ree to r econsider Rivera
, we would reach the same result. As we ex p lained there, “the lang uag e of § 994(h) sug g e sts that the p redicate drug c onvictions need
not be federal as long as they are for conduct that could have been char ge d f

e derally .” 996 F .2d at 996 (citing W hyte
, 892 F .2d at 1174). W e reasoned that:

Section 9 94(h)(2)(B ) p rovides that o ffenses “described in” th e federal statutes listed in that subsection serve a s p r e d icates for career offender status. I f C o n g ress had intended only federal offenses to serve as predicates for

career offender status, it c o uld have done so by providing that only “convictions obta ined under” the federal statutes would be the basis for ca r e er offender status. The fact that Cong r ess used the words “described in” indicates the focus i s n ot upon whether the predicate offense is federal or state; rather, the focus is upon the ty

pe of conduct involved.

1 Sin ce La Bo n t e , w e h av e co n sisten tly u p h eld th e sen ten ces o f d ef en d an t s w

h o w ere classif

ied as career o f

f en d ers b ased o n t h eir p rio r

co n v ictio n s f

o r state f

elo n y co n tro lled su

b stan ce o f

f en ses, w ith o u t

co m m en tin g o n th e v alid ity o f th e g u id elin es. S

ee, e.g

. , Un ited S t

a t es v. Lee
, 7 0 4 F.3 d 7 85
, 7 8 8

– 9 2 (9 th Cir. 2 0 1 2); Mitch ell
, 6 2 4 F .3 d at 1 0 27 ; Un ited S ta tes v. C

h a rles
, 58 1 F .3 d 9 27
, 9 34 (9 t h Cir. 2 0 0 9 ); Un ited S ta tes

v. Cra wfo rd
, 5 2 0 F.3 d 1 0 7 2, 1 0 7 7– 8 0 ( 9 t h C i r

. 2 0 0 8 ); U n ited S ta tes v. S a n d o va l-Ven eg a s , 2 92 F.3 d 11 01
, 1 1 06

– 07 (9 th Cir. 2 0 0 2 ). T h is

co n sisten t en f

o rcem e n t o f t

h e g u id elin es is a f

u rth er in d icatio n th at La Bo n t e did n o t d istu

rb o u r h o ld in g in Rivera

.U N I T E D S T A T E S V

. S T E W A R T 10

Id. 2 Thus, the career o ffender g ui d e lines, w hich include controlled substance offenses under both federal and state law

as qualify ing p redicate offenses, are “consistent with the type of conduct Cong ress intended t o p enaliz e” in § 994(h). Id. (emphasis added). Every ot h e r c ircuit to consider this question a g rees. See U

nited States v. Jemine
, 555 F

. App’x 624, 625 (7th Cir. 2014); U nited States v. Najar
, 2 25 F .3d 660, 2000 WL 799331, at *3 (6th Cir. 2000) ( u n p u b lished table d ecisio n ) ; United States v. Gonsalves
, 121 F .3d 1416, 1417–19 (11th Cir. 1997); Uni t e d States v. B rown , 23 F .3d 839, 840–41 (4th Cir. 1994), abrogated on other g rounds by Koon v

. United States
, 518 U.S. 81 (1996); United States v

. Consuegra
, 22 F .3d 78 8
, 7 8 9

– 90 (8th Cir. 1994); Beasley
, 12 F .3d at 282–84; W

hyte
, 892 F .2d at 1174.

Our post- Rivera decision in United States v. H eim
, 15 F .3d 830 (9th Cir. 1994), offe r s a further reason for rejecting Stewart’s challeng e. W e stated there that Cong ress did not intend § 994(h) to establish “an ex haustive list

. . . o f [ the] ty p es of cases in which terms at or close t o a u t horiz ed

max ima should be specified.” I d. at 8 32 (quoting S. Rep. No. 98-225 (1983)) (internal quotation m arks omitted). On the contrary , § 994(h) establishes only “the minimum oblig ation

o f the Commission,” U

nited S tates v. Damerville
, 27 F

. 3 d 254, 257 (7th Cir. 1994), or “the i rreducible minimum that the Commission must do by way of a career o f fe n der
g uideline,” United States v. Piper
, 35 F

. 3d 611, 618 (1st Cir.

2 Sectio n 9 9 4 (h ) “ p ro v id es a n arro w list o f d ru g o f f en ses t h at req u ire th e

‘ at o r n ear th e m ax im

u m ’ career o f

f en d er t reatm en t, in clu d in g distrib u tio n

u n d er [2 1 U.S.C.] § 8 4 1
, im po rtatio n o f certain co n tro lled su b stan ces

u n d er 2 1 U.S.C. § 9 5 2 (a), an d m an u f actu rin g an d d istrib u

tin g o n b o ard

v essels u n d er 4 6 U.S.C. § 7 05 0 3 .” Un i ted S ta tes v. Kn o x , 5 73 F.3 d 4 4 1
, 4 4 8 (7 t h Cir. 2 0 0 9 ).U N I T E D S T A T E S V

. S T E W A R T 11

1994). Under its ex tensive statutory authority to develop the
g uidelines, see 28 U.S.C. § 994(a)–(f); Unit ed States v

. Mendoza-Figueroa
, 65 F .3d 6 91, 692 (8th Cir

. 1 9 95) (en banc), the C o m m i ssion may g o bey ond the minimum requirements of § 994(h), so long as the resulting g uidelines do not c onflict with a n y “specific d irectives of Cong ress,” LaBonte
, 520 U.S. at 7 57. T h us, because section 994(h) does
not limit career offender status to defend a n t s with two predicate federal convictions, the Commission did n ot ex c eed the scope of its deleg ated authority by including prior s t a te convictions as a n additional basis for career offender status. Cf. Heim , 15 F .3d at 832.

III

Stewart also c halleng e s the substantive reasonableness o f his 120-month sentence. Neither party c halleng es the district court’s sentencing procedure, so we evaluate the substantive reasonableness of Stewart’s sentence under an a b u s e o f discretion standard. S

ee U nited States v. Edwards
, 595 F .3d 1004, 1014 (9th Cir. 2010). We c onsi d e r t h e t otality o f the circumstances, including the deg r e e of the c ourt’s variance from the g u idelines sentencing range a n d its discretionary weig hing of the factors set forth in 1 8 U.S.C. § 3553(a). See United States v. Carty
, 520 F .3d 984, 993 (9th Cir. 2008) (en banc). “[ A] lthoug h the ‘Guideli n e s s h ould be the starting point a n d t he initial benchmark,’ district courts may impose

se n t ences within statutory limits based on appropriate consideration of all of the f actors listed in § 3553(a), subject
to appellate review for ‘reasonableness.’” Pepper v

. U n ited States
, 131 S. Ct. 1229, 1241 (2011) (quoting United States

v. Gall
, 552 U.S. 38, 4 9 –51 (2007)). “[ W ] e may reverse if,
upon reviewing the record, we have a definite and f irm conviction t hat the d istrict court committed a clear error o fU N I T E D S T A T E S V

. S T E W A R T 12

judg men t i n the conclusion it r eached upon weig hing the relevant factors.” U

nited S tates v

. Ressam
, 679 F .3d 1069, 1087 (9th Cir. 2012) (en banc) ( quoting United States v

. Amezcua-Vasquez
, 567 F

. 3d 1 0 5 0
, 1055 (9th Cir. 2009)) (internal quotation marks omitted).

There is no dispute that Stewart’s third drug distribution conviction qualified him as a c areer offen d e r under the
g uidelines. As a career offender, Stewart’s offense level was set by reference to the 20-y e a r statutory max imum penalty for distributing GHB
, a penalty that applies reg ardless of the quantit y o r p urity of GHB involved in the offense. See U.S.S.G. § 4 B 1.1(b)(3); 21 U.S.C. § 8 41(b)(1)(C). 3 B a sed on this offense level and the criminal h istory c ateg ory of VI imposed b y the career o f

f e n der g uidelines, the district court correctly c alculated Stewart’s g uidelines rang e as 151 to 188 months’ i mprisonment, after a three-level d ownward adjustment for acceptance of responsibility

. Acknowledg ing its authority to depart belo w this

recomme n d e d sentencing rang e, the c o urt imposed a 120- month sentence, 31 months below t h e low end of the applicable career o ffender g uidelines rang e. Stewart

3 In th is resp ect, GHB is d if f eren t f ro m oth er co n tro lled su

b stan ces. Fo r

m a n y c o n t r o l l e d s u b s t a n c e s , i n c l u d i n g m a r i j u a n a , c o c a i n e , m eth am ph etam in e an d h ero in
, th e s tatu to ry m ax im u m is t ied to th e q u an tity o f d ru g s in v o l v e d i n th e o f f en se. S

ee 2 1 U.S.C. § 8 4 1 (b )(1 )(A )– (B ), (D). A s a co n seq u en ce, th e o f f en se l ev el u n d er th e

career of f en d er g u id elin es f

o r o f f en ses in v o lv i n g th ese d ru g s m ay in crease

as d ru g q u an t ity in creases. See U.S.S.G. § 4 B1 .1 (b ). Fo r GHB
, h o w ev er, th ere is a sin g le s tatu to ry m ax i m u m o f 2 0 y ears reg ard less o f th e qu an tity

o f GHB in v o lv ed

. T h u s, f o r p u rp o ses o f d eterm in in g Stew art’ s o f f en s e lev el u n der th e career o f

f en d er g u id elin es, th e q u an tity o f GHB in v o lv ed in h is o f f en se is im m aterial.U N I T E D S T A T E S V

. S T E W A R T 13

nevertheless arg ues that his sentence is unreasonable because of (1) the very low purity of the GHB mix ture involved in the

o f f e n s e; (2) the c areer offender g u idelines’ ov e r

representation of the seriousness of h i s c r iminal history a nd risk of recidivism; and (3) the sy stemic shortcoming s of t he

career offender provisions as applied in any case, i n c luding his.

The district cour t ex plicitly considered and rejected Stewart’s arg uments in lig ht of the g u i delines and the § 3 553(a) factors, making an “individualiz ed a ssessment based on the facts pre s e n t e d.” Gall
, 552 U.S. a t 50. As we shall ex plain, th e district court was likely mistaken in its assumption a b o u t the sig nificance of the GHB mix ture’s purity u nder the non-career offender g uidelines. Nonetheless,

we affirm the reasonableness of Stewart’s sentence u nder the totality of the circumstances. Stewart was indisputably a

career o ffender, and the d istrict c ourt c orrectly calculated his applicable g uidelines rang e and otherwise evaluated the relevant factors in sentencing him to a be l o w-g uidelines
sentence.

A. P urity or Concentration of G HB Mixture

St e wart contends that the ex tremely low purity of the GHB mix ture warranted a sig n ificant variance from the career offender g uidelines, and that e ven a below-g uideline, 120- month sentence w as unreasonable. A ccording to laboratory testing
, o ne s am p l e of the liquid Stewart sold contained 0.055% pure GHB

. A n o ther sample c ontained just 0 .046% GHB

. W hen used f

or a p p ro v ed therapeutic purposes, GHB is d istributed in a solution of 50% purity – over 900 times

more conc e n t rated than the most concentrated mix ture Stewart sold to the unde r c o v e r ag ent. Stated a nother way ,U N I T E D S T A T E S V

. S T E W A R T 14

Stewart sold about three g allons of water that contained
roug h ly five to six total g r ams of dissolved GHB

. This is the equivalent of only a sing le prescribed dose of GHB
, or a

max imum of six “doses” for illicit purposes. 4

The district court accepted Stewart’s evide n c e o f low purity but rejected h is arg ument for a variance. Agr e eing with the present e n ce report (PSR), it concluded that absent the career offender provisions, Stewart would be s e n t enced based on the e n t i r e 11 liters of the GHB mix ture he sold without reg ard to p urity , y ielding a g uidelines rang e of 46 to 57 months. 5 B ecause the d istrict court view e d purity a s irrelevant for determining d rug quantity under the g uidelines, it f ound that the very l ow p urity of the GHB mix ture was irrelevant to any variance from the career offender provisions.

W e disag ree with the district court’ s c o n clusion that Stewart’s non-career-offender sentenc i n g rang e would have been based on 11 liters of GHB . F irst, purity or dilution is a relevant consideration for c rafting a sentence that is “sufficient, but not g r eater than necessary ,” u nder § 3553(a). J ust as an upward variance or departure may be j u stified

4 See U.S. Dep ’ t o f J u stice, Dru g En f orcem en t A d m in
., Dru g s o f A b u se: A DEA Reso u rce G u i d e 5 4 ( 20 1 1 ed .) (statin g th at th e av erag e d o s e of GHB w h en illicitly u sed is ap p ro x im ately o n e t o f iv e g ram s), a va ila b le a t h ttp ://w w w .j u stice. g o v / d e a / p r/m

u ltim ed ia- lib rary /p u

b licatio n s/d ru g

_ of

_ ab u se.p d f

.

5 Un d er th e g u id elin es, o n e m i lliliter o r g ram o f GHB is th e eq u iv alen t

o f 8 .8 g ram s o f m arij u an a f or p u rp oses o f calcu l atin g a b ase o f f en se l ev el. S ee U.S.S.G. § 2 D1 .1 cm

t. n .8 (D). T h u s, w ith o u t acco u n tin g f o r p u rity
, th e 1 1 ,3 5 9 m i l liliters o f t h e GHB m ix tu r e Stew art d istrib u ted y i eld s an

o f f en se lev el o f 2 4
, an d af

ter a red u ctio n f

o r accep tan ce o f resp o n sib ility
, a g u id elin es ran g e o f 46 to 5 7 m o n th s ’ im p riso n m en t b ased o n h is categ o ry III crim in al h isto ry

.U N I T E D S T A T E S V

. S T E W A R T 15

b a s e d o n the unusually h ig h purity of a drug
, see U.S.S.G

. § 2D1.1 cmt. n.26(C), a downward variance for a mix ture o f unusually low purity may be justified in ap propriate circumstances to better reflect the n a t u re and seriousness o f the offense, see 18 U.S.C. § 3553(a)(1)–(2).

S e c o nd, the district court was likely mistaken in it s assumption about the sign i f i cance of the GHB mix ture’s purity under the non-career offender gu i d e lines. Ty p ically
, drug quantity under the g uidelines includes the entire w eig ht

or volume of any

mix ture containing a detectable amount o f

c o n t ro l l e d substance, w ithout r e ga r d t o p u r i t y o r concentratio n. See U.S.S.G. § 2 D1.1(c) n.(A). F or the weig ht or volume of a mix ture to be c onsidered in its entirety
, however, it first must be useable as an illicit drug

. See United States v. Sprague
, 135 F .3d 1301, 1305 (9th Cir. 1 998) (holding that under the “marketable material approach,” “the weig ht o f an unusable material mix ed with a controlled substance should not be included in the weig ht for sentencing ”). Therefore, a d efendant’s drug quantity “does
not include materia ls that must be separated from the controlled substance before the c o n trolled substance c an be used,” whether or n ot the m a t e r i a ls can in fact be separated. U.S.S.G. § 2D1.1 cmt. n.1; see also U nited States v. B

y field
, 391 F .3d 277, 280 ( D.C. Cir. 2004) (“[ U] sability [ is] essential for calculating the weig ht of a drug quantity f o r § 2 D1.1 sentencing purposes.”); United S t ates v. Stewart
, 361 F .3d 37 3
, 377 ( 7th Cir. 2 004) (“[ O] nly usable or consumable

m i x t u res or substances are included in the drug quantity f o r sentencing purposes.”).

W e h ave e x p lained that “packag ing material” and “t h e weig ht of waste washing s in a mix ture containing only trace amounts of a controlled substance” are two e x a m p les o fU N I T E D S T A T E S V

. S T E W A R T 16

substan c es that must “be separated from the [ controlled substance] before it could b e used.” Sprague
, 135 F .3d at 1305–06. “On the other hand, the w eig ht of a c o n s u m able cutting or diluting ag ent u sed to increase the total amount of

a marketable controlled substance would not be ex cluded as it need not be separate d t o r e nder the drug useable.” I d. at 1305 (emphasis added).

Althoug h we h ave not located any case s p ec ifically addressing hig hly diluted GHB
, courts have addressed analog ous circumstances for other controlled substances. I n Unit e d S t a t e s v. Robins
, 967 F .2d 1387 (9th Cir. 1992), for

ex a mple, we h e l d t hat the weig ht of cornmeal mix ed with cocaine should not be used in determining th e base offense level, because the 2,779 g rams o f cornmeal at issue “ h a d to be separated from the [ one-tenth of a g ram of] cocaine before the cocaine could be effectively used.” Id. at 1388–89. The cornmeal was “the functional equivalent o f packag ing material,” because the cornmeal-cocaine mix ture c ould n ot be used without separating out the drug first. Id. at 1389. A s did Stewart here, the defendant in Robins attempted to defraud an undercover ag ent by masking the very small quant i t y of a controlled substance actually being sold. Id. at 1388.

W h en confronted w ith a n unuseable or unmarketable mix ture, “ra t h e r than w eig hing every thing
, [ a district court should]

. . . include only the amount of usable or consumable substances, or the a mount of d r u g that the defendant could have ex tracted from something that is unusable at the time o f arrest.” Stewart
, 361 F .3d a t 378–79 (internal citations omitte d )

. T his log ic has been applied to an “unmarketable”

m i x ture containing over 1000 g rams of sug a r a nd only 1 0
g rams of cocaine, see United States v

. J ackson
, 115 F .3d 843, 8 4 8

– 4 9 ( 1 1 t h C i r

. 1 9 9 7 ) ; a m i x t u r e c o n t a i n i n gU N I T E D S T A T E S V

. S T E W A R T 17

methamphetamine and other substances that had to be evaporated or filtered out b efore the drug could be used, see Sprague
, 135 F .3d at 1306; a solution o f wa ste water

c o n t a ining a trace amount o f cocaine, see United State s v. Johnson , 999 F .2d 1192, 1196–97 (7th Cir. 1993); and larg e quantities o f cocaine diluted in wine or liqueur, se e U n ited States v. Palacios-Molina
, 7 F.3d 4 9, 54 (5th Cir. 1 993); United States v. Acosta
, 963 F .2d 551, 554–56 (2d Cir. 1992). But see United States v. Berroa

- M e d r ano , 303 F .3d 277, 283–84 (3d Cir. 2 0 02) (holding that a defendant who ag reed
to sell a packag e containing one kilog r am of common heroin cutting ag ents and only a trace a m o u n t of heroin is accountable for the entire weig ht of the packag e). This is in
contrast to t hose cases where, d e spite dilution o r contamination, the controlled substance mix t u re “was ready f o r sale and f

or use as it was.” U

nited States v

. C o l e m a n , 166 F .3d 428, 432 (2d Cir. 1999) (emphasis omitted).

Thus
, w h e n GHB is dissolved in water at a useable concentration, the entire v olume o f the GHB mix ture must be considered in determining drug quanti ty , because the water

serves only as a d ilutant of the GHB, f acilitating its use a

nd distribution. See Sprague
, 1 35 F .3d at 1305. On the other hand, when reliable scientific evidence sho w s t hat GHB is diluted p ast the point of usability
, the drug quantity should be based on an approx imation of the amount of usable GHB mix ture dissolved in the total liquid. See U.S.S.G. § 2 D1.1

cm t

. n

. 1

. The water is not merely a dilutant in this latter circumstance
, b u t a “material[ ] that must be separated from the [GHB ] before the [ G HB ] can be used.” Id

. An unuseable GHB mix ture “[ does] not constitute ‘a drug product moving throug h the chain of d istribution in the manner envisioned b y Cong r ess.’” Robins
, 9 67 F .2d a t 1390 (quoting United States v. Chan Y u-Chong , 920 F .2d 594, 597 (9th Cir. 1990)).U N I T E D S T A T E S V

. S T E W A R T 18

T he district court understandably did n ot analy z e t h e usability of Stewart’s GHB mix ture because Stewart did not raise the issue of usability in the dis t r i c t c ourt. W e strong ly suspect, however, that the GHB mix ture was unusable, which would have a sig nificant ef fe c t on Stewart’s non-career offender g u idelines rang e. At the concentration Stewart sold the mix ture (0.00055 g rams of GHB per milliliter of water),

o ne would have to consume about a half-gallon o f l i q u i d t o obtain a s i ng le “usable” dose of GHB
, even assuming that GHB this dilute would h ave any effect at all. I f the GHB was in fact unusabl e, the relevant b enchmark for p urposes o f sentencing would be an a pprox imation of the a m o unt o f usable mix ture he d istributed, that is, a use a ble solution containi n g s ix g rams of dissolved GHB

. See Stewart
, 361 F .3d at 378–79 (holding that a court must determine “the
amount of drug that the defendant could have ex tracted from something that is unusable at the time of arrest ”); Acosta
, 963 F .2d at 555 (holding that a sentence should “be based on the amount of the usable mix ture – not the p u re cocaine, but the cocaine mix ed with the ing estible cutting ag ents” (citing United S tates v. Rolande-Gabriel
, 9 38 F .2d 1231, 1237 (11th Cir. 1991)). 6
, 7

6 Here, f o r ex am p l e, th e d ru g q u an tity

m ig h t b e o n e liter o r less, b ased

o n th e to t al v o lu m e o f liq u i d i n w h i ch six g ram s o f p u re GHB co u ld b e d ilu ted to p ro d u ce a u s ab le p ro d u ct.

7 T h e d i s trict co u rt also reaso n e d t h a t n o v arian ce w as w arran ted b eca us e , g iv en th e p rice S tew art ch arg ed f or th e GHB
, h e “ in ten d ed h is b u y ers to b eliev e th at h is pro du ct w as o f a su f f icien t p u rity to p ro d u ce an in ten d ed ef

f ect.” In th ese circu m stan ces, th e co u rt co n clu d ed th at Stew art

w o u ld b e h eld a c c o u n t a b le f o r th e en t ire v o lu m e o f th e GHB m ix tu re

u n d er th e n o n

- career o f

f en d er g u id el i n e s , w h eth er o r n o t th e GHB w as

u sab le. W e ag ain d isag ree. A def en d an t w h o ag rees t o sell a sp e c i fi ed
q u an tity of a co n tr o l led su b stan ce is ty

p ically h eld acco u n tab le f o r th e ag reed

- u p on qu an tity
, “ u n less th e sale is co m p leted an d t

h e am o u n tU N I T E D S T A T E S V

. S T E W A R T 19

According ly
, Stewart’s non-career offender g uidelin e s rang e likely would h ave been far lower than t he 46 to 57 months calculated by the district court, based o n a much smaller volume of usable GHB mix ture. Moreover, whether

or not the district court miscalculated Stewart’s non-car e er offender rang e, the purity or diluteness of a drug mix ture can be a relevant f

actor for determining whether a sent e n ce is “sufficie n t , but not g reater than necessary ” under § 3553(a). The district court was incorrect to presume otherwise.

B. Career Of

f ender G uidelines

Stewart also arg ues that his sentence is unreasonable because the c areer offender g uide lines over-represent the seriousness of his criminal history and risk of recidivism, a nd that the these p r o visions are inherently f lawed as applied in
any c ase. He contends he was a l o w -level dealer selling drug s to support his own addiction, and his two past d rug distribution crimes were only minor offens e s

. The district
court rejected his arg uments, althoug h it nonetheless varied downward, and its reasoning is supported by

the record.

The court properly r ecog n iz ed that it could g ive less deference to or depart f

rom the ca r e er offender provisions based on either Stewart’s individual circumstances or a g eneral policy disag reement with the provisions, see United States v. Henderson
, 6 49 F

. 3 d 955, 964 (9th Cir. 2 011);

d eliv ered m o re accu rately ref lects t h e s cale o f th e o f

f en se.” U.S.S.G. § 2 D 1 .1 cm

t. n .5 (em p h asis ad ded ). Here, Stew art m ay h av e ag reed to sell
g allo n s of u sab le GHB to th e ag en t , b u t h e d eliv ered a larg e am o u n t o f an ap p aren t ly

u n u sab le p ro d u ct. P ro perly tak i n g u sab i lity in to acco u n t, th e

am o u n t of u sab le d ru g p ro d u ct Stew art d eliv ered w o u ld “ m o re accu rately ref l ect[] th e scale o f

[h is] o f f en se.” Id

.U N I T E D S T A T E S V

. S T E W A R T 20

United States v. Mitchell
, 6 24 F

. 3d 1023, 1027–30 (9th Cir. 2010), but it found that application of these provisions would
not “result[ ] in a sentence g reater than necessary ” in this c ase. I n the court’s view, Stewart had “demonstrated a willing n ess to eng ag e in criminal conduct,” and it accurately observed that “both o f his prior convicti o n s a s with the present conviction concern not o nly a series o f e scalating transactions but a demonstrated willing ness

. . . to eng ag e in s a l es o f
g reater amounts of the controlled substances.” The court’s determination that “[ d] espite two prior convictions, each with increasing ly severe sentences, [ Stewart] has demonstrated th a t he will not b e deterred f rom further criminal a ction,” is
suppo r t e d b y the r ecord. The district court therefore reasonably concluded that the substantial increase in sentence called for by the c are e r offender provision was not “unwarranted or g reater than necessary in the circumstances of this case,” because it would serve “to protect the public from further criminal action by [ Stewart] .”

Stewart h as a different view of the seriousness of his past offenses than the district court, b ut t h e district court’s interpretation o f Stewart’s criminal history and potential for recidivism was not “illog ical, implausible, or without support in inferences that may be drawn f rom the facts in the record.” United S tates v. Treadwell
, 593 F .3d 990, 999 (9th Cir. 2 010) (quoting United States v. Hinkson
, 585 F .3d 1 247, 1263 (9th C ir.2009) ( en banc)) (internal quotation marks omitted). I t s finding s also accord with the policy behind the career offender g u idelines, w hich focuses on enhanci n g t h e penalties of r ecidivist distributors of controlled substances. S ee Rivera
, 996 F .2d at 996; United S tates v. Sanchez
, 517 F .3d 6 51, 668 (2d Cir. 2 008) (“[ Section] 994(h) reflects C o n g ress’s p olicy judg ment that

. . . drug trafficking f elonies g e nerally warrant

more severe sentences w hen co m m itted by recidivists thanU N I T E D S T A T E S V

. S T E W A R T 21

w h e n committed by first- or second-time offenders.”). Th e district c ourt c ould h ave disag r eed with the p o licy behind the

career o ffender g uidelines a nd sentenced Ste w a

r t a c c o r d i n g ly
, bu t i t w a s not required to do so. See Mitchell
, 624 F .3d at 1030.

C. Totality of

the Circum stances

Considering the totality of the circumstances, the district
court did not a

buse its discretion in sentencing Stewart to 120 months’ imprisonment. As ex plained, the district c ourt relied

on a mistaken assumption w hen it declined to v ary from the

career offender g uidelines based o n the purity of the GHB

m i x ture. B ut we are not persuaded the mistake affected t h e court’s choice o f sentence or the o verall reasonableness of the
sentence it chose. The purity and usability of a drug mix ture

are but a few of the many relevant factor s t h a t w eig h into imposition of a

n individualiz ed sentence under § 3553(a). Cf. Treadwell
, 593 F .3d at 1012. F u ndamen tally
, the district
court based Stewart’s sentence on its ag re e m ent with the sentencing rang e provided by the career offender g uidelines,

a rang e that does not depend on the quantity o f GHB – usable or otherwise – involved in an offense. The court reasonably

e x p lained why no v ariance from these provisions would b e justified b ased on Stewart’s criminal h istory

. I t then varied downward by 31 months from the low end of Stewart’s career offender g uidelines rang e with t he h ope that Stewart would rehabilita t e h imself while incarcerated. W e afford “due deference to the D istrict Court’s reasoned and r e a sonable decision that the § 3553(a) factors, on the whole, justified the sentence.” G all
, 552 U.S. at 59–60. Althoug h w e may “think

a different sentence is a p p ro p r iate,” Carty
, 5 20 F .3d at 993, the district cour t did not make “a clear error of judg ment in the conclusion it r eached u pon weig hing the relevant factors,”U N I T E D S T A T E S V

. S T E W A R T 22

Ressam
, 679 F .3d at 1087 (quoting Amezcua-Vasquez
, 567 F .3d at 1055) (internal quotation marks omitted).

IV

F or the foreg oing reasons, we affirm Stewart’s sentence.

AF F IRMED.