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Date: 11-22-2021

Case Style:

United States of America v. Brent Hercules a/k/a Herc, a/k/a B

Case Number: 18-1965

Judge: Bruce M. Selya

Court: United States Court of Appeals For the First Circuit

Plaintiff's Attorney: Benjamin M. Block, Assistant United States Attorney, with
whom Halsey B. Frank, United States Attorney

Defendant's Attorney:

Boston, MA - Best Criminal Defense Lawyer Directory


Boston, MA - Criminal defense lawyer represented defendant with a transporting drugs into central Maine for distribution charge.

Because this sentencing appeal follows a guilty plea, we
gather the relevant facts from the change-of-plea colloquy, the
undisputed portions of the presentence investigation report (PSI
Report), and the transcript of the disposition hearing. See United
States v. Narváez-Soto, 773 F.3d 282, 284 (1st Cir. 2014).
Beginning in September of 2015, defendant-appellant Brent Hercules
participated in a conspiracy to transport drugs into central Maine
for distribution. During a period of approximately eleven months,
the appellant drove vehicles carrying drugs, drug dealers, and/or
drug proceeds between New York and Maine once or twice each week.
In May of 2017, the hammer fell: a federal grand jury
sitting in the District of Maine charged the appellant with one
count of conspiracy to distribute and possess with intent to
distribute controlled substances, see 21 U.S.C. §§ 841(a)(1), 846,
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and one count of possession with intent to distribute the same,
see id. § 841(a)(1). After some preliminaries, not relevant here,
the appellant pleaded guilty to both counts. When prepared, the
PSI Report revealed that the appellant had been born in the British
Virgin Islands in 1986 and had immigrated to the United States
with his parents when he was three years of age. He became a
lawful permanent resident in July of 1999. By the time of
sentencing, U.S. Immigration and Customs Enforcement (ICE) had
filed a detainer against the appellant with an eye toward
subsequent deportation.
Prior to the disposition hearing, the appellant
submitted a sentencing memorandum in which he asserted that he was
certain to be deported after serving his sentence. He therefore
beseeched the sentencing court, when mulling the factors
delineated in 18 U.S.C. § 3553(a), to consider his future
deportation and the possibility of a downward variance on that
basis.1 The government opposed this entreaty, contending that the
appellant's deportation was not a "foregone conclusion" and that
1 A variance is a non-guidelines sentence that "result[s] from
a court's consideration of the statutory sentencing factors
enumerated in 18 U.S.C. § 3553(a)." United States v. RodríguezReyes, 925 F.3d 558, 567 (1st Cir.) (quoting United States v.
Aponte-Vellón, 754 F.3d 89, 93 (1st Cir. 2014)), cert. denied, 140
S. Ct. 193 (2019); see United States v. Heindenstrom, ___ F.3d
___, ___, No. 18-2187, slip op. 1, 10-11 (1st Cir. 2019).
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a criminal defendant's potential deportation was an inappropriate
ground for imposing a downwardly variant sentence.
The district court addressed this dispute at the outset
of the disposition hearing. The court enumerated three reasons
why it would not take the appellant's potential future deportation
into account either as a sentencing factor or, by extension, as a
basis for lowering the appellant's sentence.
First, the court stated that although there was surely
"a risk" that the appellant would be deported after serving his
sentence, it was "not at all convinced that [he] will, in fact, be
deported." In support, the court noted shifting immigration
enforcement priorities among various presidential administrations,
particularly with respect to "individuals like the [appellant,]
who was brought here as a child." In a similar vein, the court
noted that the appellant had two prior state drug convictions,
neither of which had triggered his deportation.2 Given what it
characterized as the "uncertainty" surrounding the appellant's
deportation, the court expressed discomfort with reducing his
sentence based on a future event that might never occur.
Second, the court explained its view that potential
future deportation qualifies as a "collateral consequence" of
2 The PSI Report indicates that these two state convictions
were misdemeanors, but the district court initially referred to
them as felonies. The court, though, accurately described the
substance of these convictions later in the disposition hearing.
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committing a federal criminal offense. Even though the court
recognized that it was not "forbidden from considering" collateral
consequences, it described such consequences as difficult to
assess inasmuch as every defendant potentially faces wide-ranging
repercussions as a result of a federal criminal conviction
(including difficulty securing employment and strained personal
and familial relationships).
Third, the court highlighted its "greatest concern" with
considering the possibility of future deportation: that placing
such a factor into the mix might lead inexorably to sentencing
disparities between citizen- and noncitizen-defendants. In the
court's judgment, it would be "fundamentally wrong" to reduce a
noncitizen-defendant's sentence because of potential future
deportation when comparable arguments about immigration status
"would not be available" to a similarly situated citizendefendant.
Relying on these reasons, the court determined that it
would not give weight to the appellant's potential deportation
when fashioning the appellant's sentence. Later on, the court
reiterated its view that it had "the discretion to consider
deportation" but that "this is not the right case to do it."
Without objection, the district court proceeded to adopt
the guideline calculations limned in the PSI Report, set the
appellant's total offense level at 29, and placed him in criminal
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history category III. These computations yielded a guideline
sentencing range (GSR) of 108 to 135 months. The government
recommended a bottom-of-the-range sentence (108 months).
Stressing his acceptance of responsibility and his relatively
limited role as a driver for the drug ring, the appellant sought
a downwardly variant 60-month sentence.
After weighing the pertinent section 3553(a) factors,
the district court varied downward (albeit not on the basis of the
appellant's potential deportation) and imposed an 87-month term of
immurement. In explaining its sentencing rationale, the court
acknowledged the large amount of drugs and drug proceeds that the
appellant had transported and found that the appellant had played
a "limited but essential role" in the conspiracy. The court noted,
however, that the appellant had neither performed a managerial
role in the conspiracy nor engaged directly in distribution.
Along with the prison sentence, the district court
imposed a three-year term of supervised release, attaching several
special conditions. These special conditions included a
stipulation that the appellant be surrendered to ICE after serving
his prison sentence and, "[i]f ordered deported," remain outside
the United States during the period of supervised release.
This timely appeal followed.
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When confronted with claims of sentencing error, we
engage in a two-step pavane. See United States v. FloresMachicote, 706 F.3d 16, 20 (1st Cir. 2013). To begin, we inquire
into any alleged procedural errors, such as miscalculating the
GSR, failing to consider the section 3553(a) factors, or basing a
sentence on clearly erroneous facts. See id. If the sentence
proves procedurally sound, we then inquire into its substantive
reasonableness. See id.
At each step of this bifurcated analysis, the abuse-ofdiscretion standard governs our review. See Gall v. United States,
552 U.S. 38, 51 (2007); Narváez-Soto, 773 F.3d at 285. This
standard is not monolithic: under its umbrella, we review findings
of fact for clear error and questions of law (including those
involving the application and interpretation of the sentencing
guidelines) de novo. See Narváez-Soto, 773 F.3d at 285.
The appellant's principal plaint is that the district
court misapprehended the likelihood of his future deportation.
Specifically, he submits that the court erred by deeming his future
deportation merely "possible," when in point of fact "he is subject
to mandatory deportation with no possible relief." In the
appellant's view, this misapprehension infected the district
court's decision not to consider his future deportation when
crafting an appropriate sentence.
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Before grappling with the appellant's arguments, we
pause to locate them within the applicable analytic framework. In
his opening brief, the appellant did not explicitly characterize
his argument about the inevitability of deportation in terms of
either procedural or substantive error. The government, though,
characterized this argument as a claim of procedural and factual
error, and the appellant has not disputed this characterization.
Consequently, we treat the appellant's argument about the
likelihood of his deportation as a claim of procedural (and more
specifically, factual) error.
Against this backdrop, we turn to the district court's
determination that the appellant's future deportation was possible
but not a sure thing. We review this factual determination for
clear error. See United States v. Fields, 858 F.3d 24, 29 (1st
Cir. 2017). Clear error review is deferential and "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.'" Id. (quoting United States v.
Demers, 842 F.3d 8, 12 (1st Cir. 2016)). When a sentencing court
faces "more than one plausible view of the circumstances, [its]
choice among supportable alternatives cannot be clearly
erroneous." Id. at 30 (quoting United States v. Ruiz, 905 F.2d
499, 508 (1st Cir. 1990)).
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Here, it cannot be gainsaid that the appellant is quite
likely to be deported to his homeland (the British Virgin Islands)
once he has served his prison sentence. After all, the appellant's
convictions are for aggravated felonies. See 8 U.S.C.
§ 1101(a)(43)(B) (defining "aggravated felony" to comprise "drug
trafficking crime[s]" under 18 U.S.C. § 924(c)); 18 U.S.C.
§ 924(c)(2) (defining "drug trafficking crime" to include "any
felony punishable under the Controlled Substances Act"). This
status entails wide-ranging consequences. As a general matter,
noncitizens convicted of aggravated felonies are deportable under
federal law.3 See 8 U.S.C. § 1227(a)(2)(A)(iii). In turn,
deportable noncitizens "shall, upon the order of the Attorney
General, be removed" from the United States. Id. § 1227(a). And
the appellant's aggravated felony convictions render him
ineligible for various forms of relief from removal. See id.
§ 1229b(a)(3) (cancellation of removal); id. § 1231(b)(3)(B)(ii)
(withholding of removal); id. § 1158(b)(2)(A)(ii), (B)(i)
(asylum). Theoretically, then, "removal is practically
inevitable" under contemporary law for noncitizens who commit
removable offenses. Padilla v. Kentucky, 559 U.S. 356, 363-64
3 Noncitizens convicted of violations of federal, state, or
foreign laws relating to controlled substances are also deportable
under federal law. See 8 U.S.C. § 1227(a)(2)(B)(i). There is an
exception to this rule. See id. (memorializing "own use" exception
relating to single offense for possession of 30 grams or less of
marijuana). That exception is not relevant here.
- 10 -
(2010). What is more, the Supreme Court has noted that the risk
of removal is especially pronounced for noncitizens convicted of
offenses "related to trafficking in a controlled substance"
because discretionary relief from removal is generally "not
available" for such individuals. Id. at 364.
But despite the high likelihood of the appellant's
eventual deportation under the current statutory scheme,4 we cannot
say that the district court clearly erred by deeming the
appellant's future deportation uncertain. In practice,
enforcement of the immigration laws has not always been a model of
consistency, and the district court plausibly noted that the
immigration enforcement priorities of the Executive Branch "seem
to be in flux," changing with the ebb and flow of political tides.
So, too, the court correctly observed that the appellant had not
been deported in the past notwithstanding two prior convictions
for state drug offenses. See 8 U.S.C. § 1227(a)(2)(B)(i)
(establishing that noncitizens convicted of violations of state
controlled substances offenses are deportable). Relatedly, the
court commented on the appellant's 2007 state felony conviction
for attempted criminal possession of a weapon. Although this
4 We think it worth noting that the appellant did not cite
either the statutory scheme or the Padilla decision before the
sentencing court. Instead, he based his argument about his
virtually certain deportation on the ICE detainer and generic
assertions that, for instance, he would "in all likelihood" be
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conviction almost certainly rendered the appellant deportable, see
id. § 1227(a)(2)(C) (deeming noncitizens convicted under any law
for attempted possession of firearm deportable), the record
contains no evidence that this conviction ever triggered any
proceedings aimed at the appellant's deportation.
Given the substantial possibility of shifting
immigration policies and fluctuating enforcement priorities during
the appellant's lengthy 87-month incarcerative term, the district
court's determination that the appellant's future deportation was
not a matter of absolute certainty was a reasonable assessment of
the appellant's circumstances. Consequently, we hold that the
district court's finding as to the likelihood of the appellant's
future deportation was not clearly erroneous. See Fields, 858
F.3d at 30.
This brings us to the district court's decision not to
consider the appellant's potential deportation when calibrating an
appropriate sentence. Our review is under the abuse-of-discretion
rubric. See id. at 28.
In an earlier case involving a conviction for illegal
reentry under 8 U.S.C. § 1326(a), we rejected a defendant's
argument that the sentencing court should have imposed a nonguidelines sentence on the basis of his "immediate detention and
likely future deportation once released from prison." United
States v. Jiménez-Beltre, 440 F.3d 514, 520 (1st Cir. 2006) (en
- 12 -
banc), abrogated on other grounds by Rita v. United States, 551
U.S. 338 (2007). There, the defendant argued that his potential
future deportation "made a normal guideline sentence unnecessary
for deterrence or public protection and was a pertinent factor
under 18 U.S.C. § 3553(a)(2)." Id. Dismissing these arguments,
we observed that because the "crime in question — re-entry after
deportation — is ordinarily going to be committed by persons who
will be deported after their sentences have been served," the GSR
"was likely predicated on this understanding." Id. We added that
the defendant in that case, who had reentered the United States
after deportation, was "hardly in a good position to argue for a
shorter sentence on the ground that another deportation of him
will protect the public adequately against yet another
repetition." Id.
We have not yet had occasion, though, to explore a
sentencing court's ability to consider a defendant's potential
deportation outside the illegal reentry context. Like several
other courts of appeals, see, e.g., United States v. Flores-Olague,
717 F.3d 526, 535 (7th Cir. 2013) (observing that a "sentencing
court is well within its prerogatives and responsibilities in
discussing a defendant's status as a deportable alien" when
considering a defendant's history); United States v. Petrus, 588
F.3d 347, 356 (6th Cir. 2009) (acknowledging that sentencing court
may consider defendant's "potential deportation" and "immigration
- 13 -
status"), we now hold that a sentencing court has the discretion,
in an appropriate case, to weigh the possibility of future
deportation when mulling the section 3553(a) factors in an effort
to fashion a condign sentence.5
Under appropriate circumstances, a defendant's potential
deportation may properly be considered as part of a broader
assessment of his history and characteristics pursuant to section
3553(a)(1). On the right factual record, a defendant's potential
deportation also may prove relevant to whether a sentence will
adequately "protect the public from further crimes of the
defendant." 18 U.S.C. § 3553(a)(2)(C). Future threats to the
community might conceivably be mitigated in a situation in which,
upon release from imprisonment, the defendant will promptly be
deported. Cf. United States v. Morales-Uribe, 470 F.3d 1282, 1287
(8th Cir. 2006) (making this point but concluding that defendant's
impending deportation "would not support a substantial downward
variance" on this basis since defendant had thrice attempted
unlawful entry).
This is not to say that a sentencing court always must
consider a defendant's potential deportation when fashioning an
5 The out-of-circuit decisions cited in this opinion discuss
potential deportation in a variety of factual contexts. We cite
these opinions to support general legal propositions, without
implying endorsement of each court's specific application of those
- 14 -
appropriate sentence. Moreover, we expect that variances from the
GSR on this basis, although permissible in the right factual
context, will likely prove rare. In the last analysis, though,
"[s]entencing is much more an art than a science," and the weight
to be given relevant data points "is largely within the
[sentencing] court's informed discretion." United States v.
Clogston, 662 F.3d 588, 593 (1st Cir. 2011). We think it follows
that a sentencing court does not perforce abuse its discretion by
declining to speculate on a defendant's potential future
deportation. See United States v. Gomez-Jimenez, 750 F.3d 370,
384 n.8 (4th Cir. 2014). Thus, our holding here simply adds to
the chorus of circuit courts recognizing that, in the relatively
rare circumstances in which potential future deportation is an
arguably appropriate sentencing factor, a district court does not
abuse its discretion either by weighing or declining to weigh that
factor in its sentencing calculus under section 3553(a). See,
e.g., id.; Flores-Olague, 717 F.3d at 535.
In this instance, the district court expressed some
general reservations about taking a defendant's potential future
deportation into account. Withal, the court did not categorically
foreclose the consideration of a defendant's potential deportation
in all cases. To the contrary, the court stated explicitly that
it had the discretion to consider the likelihood of future
deportation in the "right case." Seen in this light, the court
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did not run afoul of the longstanding principle that "generally
courts should not categorically reject a factor as a basis for"
deviating from a guidelines sentence. United States v. Olbres, 99
F.3d 28, 34 (1st Cir. 1996); see Koon v. United States, 518 U.S.
81, 106-07 (1996) ("Congress did not grant federal courts authority
to decide what sorts of sentencing considerations are
inappropriate in every circumstance.").
The record makes manifest that three factors informed
the district court's decision that this was not an appropriate
case in which to take the likelihood of the appellant's future
deportation into account. These factors included the court's
assessment that the appellant's future deportation was
"speculative"; its conclusion that future deportation would be a
"collateral consequence" of committing a federal crime; and its
concern that reducing a noncitizen's sentence because of the
prospect of future deportation could create sentencing disparities
vis-à-vis similarly situated citizen-defendants. Nothing in the
sentencing transcript or elsewhere in the record suggests that the
court gave any one of these variables dispositive weight. Where,
as here, a sentencing court declines to factor into the sentencing
calculus a defendant's potential future deportation because of an
amalgam of appropriate concerns, no abuse of discretion occurs.
In sum, a sentencing court enjoys wide discretion to
"custom-tailor an appropriate sentence" using a "flexible, case-
- 16 -
by-case approach." Flores-Machicote, 706 F.3d at 20-21. The
district court's decision not to consider the appellant's
potential future deportation in the case at hand falls comfortably
within the ambit of this wide discretion. Here, moreover, the
district court did not clearly err by determining that deportation
was not absolutely certain to transpire. And to the extent that
the appellant "seeks to substitute his judgment" about the
relevance of his potential deportation for the contrary judgment
of the district court, "[w]e cannot countenance such a
substitution." Clogston, 662 F.3d at 593.

Outcome: We need go no further.6 For the reasons elucidated
above, the appellant's sentence is

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