United States v. Caetano Oliveira

United States Court of Appeals
For the First Circuit
No. 17-2102
UNITED STATES,
Appellee,
v.
CAETANO OLIVEIRA,
Defendant, Appellant.
APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF MASSACHUSETTS
[Hon. Nathaniel M. Gorton, U.S. District Judge]
Before
Lynch, Thompson, and Kayatta,
Circuit Judges.
Samia Hossain, Assistant Federal Public Defender, with whom
Jessica P. Thrall, Assistant Federal Public Defender, was on brief
for appellant.
Alexia Rhae De Vincentis, Assistant United States Attorney,
with whom Caitlin E. Keiper, Special Assistant United States
Attorney, and Andrew E. Lelling, United States Attorney, were on
brief for appellee.
October 24, 2018

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LYNCH, Circuit Judge. Brockton, Massachusetts police
arrested Caetano Oliveira in August 2016 while executing a search
warrant on an apartment in which drugs, drug paraphernalia, guns,
and ammunition were found. Following a federal indictment,
Oliveira pleaded guilty to being a felon in possession of a
handgun, a pistol, and twenty rounds of ammunition in violation of
18 U.S.C. § 922(g)(1). His prior state convictions included drug
distribution and assault with a dangerous weapon ("ADW").
Oliveira requested a sentence of forty-eight months.
The government recommended 100 months, a sentence at the bottom of
the 100- to 120-month range calculated in the presentence report
("PSR"). The district court sentenced Oliveira to eighty-six
months, fourteen months below the government recommendation. The
district court could have reached the same sentence within the
guideline range, but calculated the sentence on the basis of an
enhancement.
Appealing this sentence, Oliveira first disputes the
district court's determination that his prior Massachusetts ADW
conviction qualifies as a "crime of violence" under the United
States Sentencing Guidelines ("the Guidelines"). Second, he
challenges the district court's application of a sentencing
enhancement for possession "in connection with" another felony.
See U.S.S.G. § 2K2.1(b)(6)(B). We affirm.

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In the summer of 2016, Brockton police had been
investigating a heroin dealer, Sariah Lynn Miranda, who lived in
the apartment where Oliveira was arrested. After buying heroin on
multiple occasions from Miranda through a confidential informant,
police obtained a search warrant for Miranda's apartment. Once
inside, police found five grams of heroin, cash, a scale, and drug
packaging materials in the bedroom occupied by Miranda. As Miranda
attempted to leave -- with three more grams of heroin in hand --
police arrested her.
In the apartment's second bedroom, police encountered
Oliveira, whose girlfriend, Saneta Gomes, was an occupant of the
apartment and Miranda's sister. There, police found, at the end
of the bed, a shoe box containing $160 in cash and 7.6 grams of
marijuana packaged into three separate sandwich bags. A digital
scale was perched on a shoe rack. And a box of empty sandwich
bags was visible on top of the dresser.
Inside that dresser were two loaded weapons -- a 9mm
handgun and a .40 caliber pistol. There were eight rounds of 9mm
ammunition and twelve rounds of .40 caliber ammunition. The
handgun, which had been reported stolen, was located on the
dresser's shelf, while the pistol was stashed, with some clothes,
inside an orange clothing cube.

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Atop the dresser, police also spotted a copy of
Oliveira's resume. Clothing and mail belonging to Oliveira were
also found around the room. Although the resume and mail listed
addresses for Oliveira other than the apartment, Gomes, who lived
in the room, told police, "he stays here a lot."
Oliveira and Gomes were arrested, and Oliveira admitted
that the guns were his. Asked later by a detective why he had the
guns, the defendant answered, "I still have people on the street
that don't like me."
At the time of his arrest, Oliveira was out on bail,
awaiting trial in Massachusetts on charges of ordering an associate
to shoot at two undercover police officers who were talking to an
informant. During the trial on those charges, in September 2016,
Oliveira pleaded guilty to ADW. This was his third state
conviction. Oliveira's first two state convictions were in 2011
for illegal gun possession and distribution of crack cocaine. 1
After Oliveira's guilty plea to the federal charges, the
Probation Office prepared a PSR, which recommended a base offense
level ("BOL") of 24 based on Oliveira's prior "two felony
convictions for either a crime of violence or a controlled
substance offense." U.S.S.G. § 2K2.1(a)(2). In 2016, the First
1 Another charge for possession with intent to distribute
while carrying a loaded firearm was vacated in 2017 due to
misconduct at the state drug lab.

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Circuit had held in United States v. Fields, 823 F.3d 20, 34-35
(1st Cir. 2016), that Massachusetts ADW is a "crime of violence"
under the Guidelines.
The PSR also recommended several adjustments to this
BOL. Relevant is a four-level increase under U.S.S.G.
§ 2K2.1(b)(6)(B) for "possess[ion] . . . in connection with another
felony offense," which applied based on the evidence in the bedroom
of possession with intent to distribute marijuana. In the end, a
total offense level ("TOL") of 27 was calculated.
In calculating Oliveira's criminal history category
("CHC") of IV, the PSR considered the past convictions for gun
possession, crack cocaine distribution, and for assaulting the
police officers. Also relevant was Oliveira's past membership in
the Ames Street/Flameville Legend Boys gang in Brockton.
At the sentencing hearing on October 25, 2017, the
district court considered Oliveira's objections to the PSR.
Oliveira first argued that Massachusetts ADW is not a "crime of
violence" under the Guidelines and that therefore his BOL and CHC
should be lower. The district court overruled the objection,
"follow[ing] the First Circuit," where that crime "is considered
a crime of violence."
As to the enhancement under U.S.S.G. § 2K2.1(b)(6)(B),
Oliveira contended that no "felony" had occurred. He asserted
that the marijuana, bags, and scale were for Gomes's personal use,

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not for distribution. In his sentencing memorandum, Oliveira had
noted that the state had charged Gomes, not Oliveira, with
possession with intent to distribute. After that charge was
reduced to simple possession, a civil infraction, she admitted
responsibility and paid a fine. In any event, Oliveira continued,
the connection between the alleged drug trafficking and the guns
was too remote to permit application of the enhancement.
The district court found there was "ample evidence to
show that the Defendant was fully involved with this potential
distribution of marijuana." And it determined that the enhancement
was appropriate because "a firearm [was] found in close proximity
to drugs, drug-manufacturing materials or drug paraphernalia."
As mentioned, the district court sentenced Oliveira to
eighty-six months in prison and to three years of supervised
release during which he is not to enter Brockton and not to
associate with members of the Flameville Legend Boys/Ames Street
gang. Oliveira's involvement in multiple gang-related shootings
was discussed at the sentencing hearing. In one incident, Oliveira
had been the target but his sixteen-year-old girlfriend, who was
standing next to him, was killed. Just months before this
incident, Oliveira had been shot in the head, suffering permanent
hearing damage. At the sentencing, the defendant acknowledged, "I
need to leave Brockton. . . . My problems are in Brockton." The
district court "imposed a sentence 15% below the low end of the

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Guideline range to reflect defendant's effort to improve his
situation and willingness to comply with the geographic and
associational restrictions imposed."
We examine the two issues on appeal, in turn.
First, questions of Guidelines interpretation --
including what counts as a "crime of violence" -- are reviewed de
novo. See United States v. Cannon, 589 F.3d 514, 516-17 (1st Cir.
2009). As the district court noted, it is settled First Circuit
law that Massachusetts ADW is a "crime of violence" under the
Guidelines. In United States v. Whindleton, 797 F.3d 105, 115-16
(1st Cir. 2015), we held that the offense categorically qualifies
as a "violent felony" under the force clause of the Armed Career
Criminal Act. And because the definition of "violent felony"
"mirrors" the definition of "crime of violence" in the Guidelines,
United States v. Montoya, 844 F.3d 63, 73 (1st Cir. 2016), we held
in Fields that Massachusetts ADW is a "crime of violence" under
the Guidelines, 823 F.3d at 34-35. Fields remains good law. 2
Second, Oliveira challenges on several grounds the
enhancement for possession "in connection" with another felony
under U.S.S.G. § 2K2.1(b)(6)(B). A district court must find that
2 Indeed, Oliveira acknowledges that precedent forecloses
his objection, but "raises the argument to preserve it for further
review on certiorari to the Supreme Court."

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a preponderance of the evidence supports the enhancement to apply
it. United States v. Paneto, 661 F.3d 709, 715 (1st Cir. 2011).
We then review the district court's underlying findings of fact
for clear error and its application of the Guidelines to those
facts on a "sliding scale." United States v. Matthews, 749 F.3d
99, 105 (1st Cir. 2014); see also Cannon, 589 F.3d at 516-17.
That standard of review decides this issue. We cannot
say that the district court clearly erred. As we will detail, the
district court applied the enhancement based on a chain of
inferences, including that there was distribution of the drugs
found in the bedrooms along with drug paraphernalia, that Oliveira
knew of and participated in this, and that illegal guns and
ammunition were connected to the distribution. That chain may be
tenuous. But, under the clear error standard, as long as these
inferences were "rational," and we believe that they were, we
cannot reverse. A "sentencing court's choice among rational but
competing inferences cannot be clearly erroneous." Matthews, 749
F.3d at 105; see also Cannon, 589 F.3d at 517. Admittedly, some
of those factual inferences were built on thin evidence. Yet the
clear error standard means that we "will not reverse" factual
findings "absent 'a strong, unyielding belief that a mistake has
been made.'" United States v. Gómez-Encarnación, 885 F.3d 52, 56
(1st Cir. 2018) (quoting United States v. Torres-Velazquez, 480

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F.3d 100, 103 (1st Cir. 2007)). As we will explain, we lack that
strong, unyielding belief here.
The district court found felony distribution, by a
preponderance of the evidence, based on the totality of the
evidence in the bedroom: the 7.6 grams of marijuana split across
three bags, in addition to the empty sandwich bags, the cash, the
scale, and the two illegal guns. These markers are "probative of
the intent to distribute narcotics." United States v. Ford, 22
F.3d 374, 383 (1st Cir. 1994). That is especially so when found
together. See Matthews, 749 F.3d at 105 (explaining that we look
at evidence of intent to distribute "in its totality"). Finally,
Miranda's heroin dealing in the other bedroom of the small
apartment buttresses the inference that the marijuana, scale,
cash, bags, and guns were possessed for distribution. In the end,
we cannot say -- with the strong, unyielding belief required of
clear error review -- that the district court made a clear error
in inferring distribution from this evidence.
We also see no clear error in the district court's choice
not to accept Oliveira's claim that the marijuana was intended
exclusively for Gomes's personal use. Gomes made no such statement
to the Probation Office. Rather, Oliveira urges that this is a
necessary implication of the plea deal Gomes struck with the state,
under which her distribution charge was reduced to simple
possession. The scale and baggies, he says, are also consistent

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with possession for personal use. Oliveira emphasizes that "the
Commonwealth [of Massachusetts] has . . . de-criminalized the
possession of less than one ounce of marijuana." 3 As a result, he
says, "it is unreasonable to automatically assume that digital
scales, cash, and sandwich bags are distribution paraphernalia."
For example, the scale could have helped Gomes "ensure [she was]
purchasing amounts [of marijuana] within the confines of the law."
None of that means there was clear error. It is not at
all obvious (and Oliveira supplied no evidence of a reason) why
Oliveira or Gomes would have kept the marijuana in numerous baggies
if it were for personal use. While plastic bags and scales have
other uses, there is neither evidence nor an assertion by Oliveira
that the bags and scale were used for, say, food preparation (and,
remember, they were found in the bedroom, not in the kitchen), or
for any other reason. Finally, near the drugs and classic drug
distribution paraphernalia, Oliveira possessed two illegal guns.
Guns are "tools of" the drug trafficking trade. See Ford, 22 F.3d
at 383. And Oliveira was a convicted practitioner of that trade
who had recently targeted undercover officers. At most, Oliveira's
theory shows that the district court chose between two possible
interpretations of the facts. What Oliveira fails to show is that
3 Under Massachusetts law, "a person 21 years of age or
older" cannot face criminal penalties for "using, purchasing,
processing or manufacturing 1 ounce or less of marijuana." Mass.
Gen. Laws ch. 94G, § 7.

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the district court's inference that the marijuana was for
distribution was irrational. We cannot say there was clear error.
The district court also did not clearly err in finding
"ample evidence" of Oliveira's involvement with the drug
distribution. Oliveira stayed in the apartment "a lot" and his
personal items -- his guns and ammunition, resume, mail, and
clothing -- were found there. Further, Oliveira was actually there
at the time of the police search, at the time the officers found
plastic bags, the digital scale, and three bags of marijuana in
one bedroom and heroin for distribution in another. Based on this,
we cannot say that the district court clearly erred in finding
that Oliveira was involved.
Oliveira's argument that this finding was improper
because neither the marijuana nor the bedroom were his misses the
mark. The bedroom, drugs, and paraphernalia need not have belonged
to Oliveira. The enhancement applies where the defendant has
access to the drugs and where his knowledge of drug distribution
can be inferred. See Cannon, 589 F.3d at 519. Oliveira's frequent
overnight stays in the room and the presence of his belongings
there indicate sufficient access. See United States v. Zavala
Maldonado, 23 F.3d 4, 7 (1st Cir. 1994) (defining constructive
possession in part as location of the object in a "domain specially
accessible to the defendant"). As to his knowledge, Oliveira
claims ignorance of the marijuana inside the shoe box and the scale

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on the shoe rack and maintains that his knowledge cannot be
inferred from awareness of the sandwich bags alone. The marijuana
and cash were found in a box at the end of the bed often shared by
Gomes and Oliveira. The particular usefulness of plastic bags and
small digi-scales for packaging drugs for resale is well known,
especially among those who, like Oliveira, have experience with
drug distribution. See Cannon, 589 F.3d at 515-19 (finding
knowledge based in part on defendant's "history of drug
distribution"). In the end, Oliveira had the requisite knowledge.
Oliveira's final argument is that the district court
erred in applying the enhancement because the guns and ammunition
were possessed for his own protection and not "in connection with"
drug trafficking. In applying the § 2K2.1(b)(6)(B) enhancement,
the district court relied on Guidelines Application Note
14(B)(ii), which states that the enhancement applies "in the case
of a drug trafficking offense in which a firearm is found in close
proximity to drugs, drug-manufacturing materials, or drug
paraphernalia." Based on this Note, we have held that the
enhancement attaches where firearms near drugs "ha[ve] the
potential of facilitating" drug trafficking. Paneto, 661 F.3d at
717 (emphasis added). Applying the enhancement was not
inappropriate, then, in light of the facts: Oliveira's firearms
were loaded and next to extra ammunition in a bedroom containing
drugs and drug trafficking materials. See id. (firearm and cocaine

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in "same small single-floor apartment"); United States v.
Sturtevant, 62 F.3d 33, 34 (1st Cir. 1995) (per curiam) ("[T]he
presence of a readily available weapon in a location containing
drugs is enough.") Oliveira's statement that he possessed the
guns for his own protection does not change this, for the simple
reason that guns can be possessed for more than one purpose.
We affirm the defendant's sentence.
-Concurring Opinion Follows-

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THOMPSON, Circuit Judge, concurring. I write separately
to draw the attention of bench and bar to the only truly troubling
aspect of this appeal — namely, the district judge's use of
inference-drawing to find felony drug distribution by a
preponderance of the evidence, thus triggering a major sentencing
enhancement for Oliveira.
I know, as the lead opinion notes, that the Federal
Reporter is teeming with First-Circuit cases letting factfinders
infer a defendant's distributive intent from the drug amounts
possessed, as well as from the possession of drug-trade
accoutrements like digital scales, baggies, cash, and guns. See
United States v. Cortés–Cabán, 691 F.3d 1, 35-36 & nn. 37, 39-41,
43, 45 (1st Cir. 2012) (citing a host of cases); see also United
States v. Matthews, 749 F.3d 99, 105 (1st Cir. 2014). And I also
know that the standard of review for assessing sentencing
enhancements — clear error — often determines the issue's outcome.
That's so because, as the lead opinion also notes, clear-error
review is incredibly deferential, requiring us to accept the
judge's fact findings absent a strong and abiding belief that he
slipped up — all while being mindful that the judge's choice
between two plausible but differing fact inferences can't be
clearly erroneous. See, e.g., Matthews, 749 F.3d at 105; Cumpiano
v. Banco Santander P.R., 902 F.2d 148, 152 (1st Cir. 1990). Which
makes showing clear error a hard task for any appellant, see, e.g.,

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Matthews, 749 F.3d at 105 — a task Oliveira has not accomplished
here.
Now here's the problem. Times have changed since we
first approved the sort of inference-drawing I just described.
Oliveira was charged federally, to be sure. But there's a
"growing" trend at the state level toward legalizing or at least
decriminalizing marijuana. See DeBartolo v. United States, 790
F.3d 775, 779 (7th Cir. 2015) (Posner, J.). Take, for example,
some of the jurisdictions in our circuit, whose relevant laws I
discuss next (without delving into every last legal detail).
Massachusetts, for example, has legalized recreational
marijuana. As the lead opinion states, a Massachusetts statute —
titled "Personal use of marijuana" — says that persons "21 years
old or older" can't be punished criminally for "using, purchasing,
processing or manufacturing 1 ounce or less of marijuana," see
Mass. Gen. Laws. Ch. 94G, § 7; Oliveira's 7.6 grams of marijuana
is less than 1 ounce (for anyone unfamiliar with the metric system,
1 ounce equals 28.3495 grams). Nor can persons 21 years old or
older be on the hook criminally "for . . . giving away . . . up to
1 ounce of marijuana . . . to a person 21 years of age or older,
as long as the transfer is not advertised or promoted to the
public." See id. And because of these developments,
Massachusetts's top court — known colloquially as the "SJC" (short
for the "Supreme Judicial Court") — has held that the mere smell

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of marijuana is "not sufficient to support a reasonable suspicion
of criminal activity." See Commonwealth v. Villagran, 81 N.E.3d
310, 317 (Mass. 2017) (citing Commonwealth v. Rodriguez, 37 N.E.3d
611, 618 (Mass. 2015)). What's more, persons 21 years old or older
can't be punished criminally in the Commonwealth "for possessing,
purchasing, or otherwise obtaining or manufacturing marijuana
accessories or for selling or otherwise transferring marijuana
accessories to a person who is 21 years of age or older . . . ."
See Mass. Gen. Laws. Ch. 94G, § 8. That statute defines "marijuana
accessories" as "equipment, products, devices or materials of any
kind that are intended or designed for . . . preparing, . . .
packaging, repackaging, [or] storing," id. — a definition
seemingly broad enough to cover digital scales and baggies, for
instance. And speaking of scales, when it comes to medical
marijuana — which Massachusetts legalized years ago — the SJC has
held that qualifying "patients may need use of a scale to weigh
the marijuana they grow, so as to ensure they do not exceed" the
amount they're legally permitted to cultivate. See Commonwealth
v. Richardson, 94 N.E.3d 819, 835 n.23 (Mass. 2018).
Rounding out the picture, Maine has also legalized
recreational marijuana. A Maine law — called "Personal adult use
of marijuana and marijuana products" — says that "person[s] 21
years of age or older" can "[u]se, possess or transport marijuana
paraphernalia" and "[u]se, possess or transport at any one time up

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to 2½ ounces of marijuana . . . ." See Me. Rev. Stat. tit. 28-B,
§ 1501. The Maine law also lets persons 21 years old or older
"[t]ransfer or furnish, without remuneration, to a person 21 years
of age or older up to 2½ ounces of marijuana . . . ." Id. New
Hampshire and Rhode Island have decriminalized marijuana,
eliminating (for the most part) the possibility of jail time for
possessing small amounts of marijuana for personal use. See
respectively N.H. Rev. Stat. Ann. § 318-B:2-c; R.I. Gen. Laws Ann.
§ 21-28-4.01. And Maine, New Hampshire, Puerto Rico, and Rhode
Island permit marijuana use for medicinal purposes. See
respectively Me. Rev. Stat. tit. 22, § 2423-A (Lexis 2018)
(effective July 9, 2018); N.H. Rev. Stat. Ann. § 126-X:2; P.R.
Laws Ann. tit. 24, § 2623b; R.I. Gen. Laws § 21-28.6-4.
Which gets me to my point. Given these recent legal
changes (with more likely on the way), perhaps someday we as a
court will have to reconsider whether a factfinder can reasonably
infer felonious intent to distribute in part from a defendant's
lawful possession — under state law, anyway — of both personal-
use marijuana and marijuana-related paraphernalia. But today is
not that day.
And having said my piece, I join my colleagues in
affirming Oliveira's sentence.

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