United States v. Rodriguez-Monserrate ( 2021 )

United States Court of Appeals
For the First Circuit
Nos. 20-1905, 20-1907
UNITED STATES OF AMERICA,
Appellee,
v.
HERMIN RODRIGUEZ-MONSERRATE, a/k/a Cano, a/k/a Canito.
Defendant, Appellant.
APPEALS FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF PUERTO RICO
[Hon. Francisco A. Besosa, U.S. District Judge]
Before
Thompson, Kayatta, and Barron,
Circuit Judges.
Arza Feldman, with whom Feldman and Feldman was on brief, for
appellant.
Robert P. Coleman III, Assistant United States Attorney, with
whom W. Stephen Muldrow, United States Attorney, and Mariana E.
Bauzá-Almonte, Assistant United States Attorney, were on brief,
for appellee.
December 30, 2021
KAYATTA, Circuit Judge. In this consolidated appeal,
Hermin Rodriguez-Monserrate raises a host of procedural and
substantive challenges to two sentences he received at hearings
conducted via videoconference during the COVID-19 pandemic. We
find that all but one of his challenges are waived or otherwise
without merit and that his remaining challenge is not yet ripe for
review. Our reasoning follows.
I.
This case arises out of the following events. In 2019,
law enforcement agents saw a gun and magazines on a ledge near a
window to the apartment occupied by Rodriguez's romantic partner.
The partner allowed agents to search her apartment while Rodriguez
was present. During the search, agents found ammunition,
marijuana, face masks, a radio scanner, and various gun holsters.
Rodriguez was arrested and admitted that most of these items were
his, though he denied owning the gun and associated magazines found
on the ledge.1 Rodriguez further admitted that, at the time of
his arrest, he had been convicted of a felony and was serving a
term of supervised release.
Rodriguez's arrest led to two actions against him.
First, the government charged him with committing a new crime:
1 Rodriguez's partner told the agents the gun belonged to
Rodriguez. Neither party contends that this factual dispute is
salient to the issues on appeal.
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possessing ammunition as a convicted felon in violation of 18
U.S.C. § 922(g)(1). Second, the government sought revocation of
his supervised release.
At an in-person hearing in February 2020, Rodriguez
pleaded guilty to the section 922(g)(1) charge pursuant to a plea
agreement in which the parties agreed to seek a prison term of
30 months. The agreement specified that Rodriguez waived his
"right to appeal any aspect of [the] case's judgment and sentence,
including but not limited to the term of imprisonment . . . and
conditions of supervised release" so long as his sentence did not
exceed 37 months.
Rodriguez's sentencing hearing on the section 922(g)(1)
conviction was scheduled to be held on the same day as the hearing
on the government's request to revoke his supervised release. By
the time those hearings were to occur, in August 2020, the COVID-
19 pandemic had caused the United States District Court for the
District of Puerto Rico to continue all in-person proceedings until
October 2020. See Third Am. Order Continuing Civil & Criminal
Proceedings, Misc. No. 20-0088 (GAG) (Aug. 25, 2020), ECF No. 21.2
Accordingly, the district court sought Rodriguez's consent to
proceed via videoconference. The court obtained that consent in
2 Both hearings had already been continued once before due
to the COVID-19 pandemic; they were previously scheduled to occur
on May 27, 2020.
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two ways. First, Rodriguez filed a motion "respectfully
request[ing] th[e] court to take note of his consent and to hold
the [sentencing] hearing via videoconference." Second, at the
start of the August 2020 proceedings, the court orally confirmed
on the record that Rodriguez's "appear[ance] by video" was
"voluntary" and that he "[did] not have to appear by video." The
court told Rodriguez that he could consent to appear by video for
both his sentencing and revocation hearings. Rodriguez consented
to conducting both hearings by videoconference.
The court sentenced Rodriguez on the section 922(g)(1)
conviction to 37 months -- the upper bound of the guideline range.
The district court also imposed as one of several conditions of
supervised release a requirement that Rodriguez "shall complete
his high school education."
The court conducted Rodriguez's revocation hearing
during the same videoconference pursuant to Rodriguez's earlier
consent. The government sought a 10-month revocation sentence
based on an estimated guideline range of 4–10 months, but the
probation officer calculated the range to be 12–18 months. The
court agreed with the probation officer and imposed an 18-month
revocation sentence, to be served consecutive to the 37-month
sentence for the section 922(g)(1) conviction.
During each hearing, Rodriguez asked the court to
reconsider the pertinent sentence. The court denied each request.
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Rodriguez now brings an array of challenges to both of
his sentences.
II.
We begin with the revocation hearing and sentence.
Unimpeded by his appeal waiver, which applies only to his sentence
for the section 922(g)(1) conviction, Rodriguez raises two types
of challenges to his revocation hearing and sentence. First, he
argues that, notwithstanding his consent to proceed by
videoconference, the district court erred in conducting the
revocation hearing in that manner. Second, he argues that his
revocation sentence was procedurally and substantively
unreasonable. For the following reasons, both claims fail.
A.
Rodriguez argues that the district court erred in
conducting his revocation hearing via videoconference because
doing so was impermissible under both Federal Rule of Criminal
Procedure 32.1 and the Coronavirus Aid, Relief, and Economic
Security (CARES) Act, Pub. L. No. 116-136, 134 Stat. 281 (2020).
Rodriguez did not raise these arguments below; rather, he consented
to proceeding via videoconference, telling the district court that
he "want[ed] to appear here and now." Hence, Rodriguez is at best
entitled to plain error review. See United States v. Delgado-
Sánchez, 849 F.3d 1, 6 (1st Cir. 2017). In his opening brief on
appeal, Rodriguez makes no attempt to satisfy that standard as to
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his arguments based on either Rule 32.1 or the CARES Act. Those
arguments are therefore waived. United States v. Pabon, 819 F.3d
26, 33–34 (1st Cir. 2016) (failure to address plain error standard
waives challenge); Waste Mgmt. Holdings, Inc. v. Mowbray, 208 F.3d
288, 299 (1st Cir. 2000) ("[I]ssues advanced for the first time in
an appellant's reply brief are deemed waived.").
Rodriguez also briefly asserts that proceeding by
videoconference "impacted his right to the effective and
meaningful assistance of counsel." Again, though, he made no claim
below that the particular video format employed by the court
impaired his ability to consult confidentially with his lawyer.
Indeed, he does not dispute that the district court explained, "If
you want to speak with your lawyer before I sentence you, or before
I make a decision on your revocation, please let us know, and we
will make arrangements for both of you to have a confidential
communication." Nor does Rodriguez develop on appeal any argument
as to how the format plainly impaired his ability to receive the
assistance of counsel. This argument is therefore both forfeited
and waived. See United States v. Zannino, 895 F.2d 1, 17 (1st
Cir. 1990) ("[I]ssues adverted to in a perfunctory manner,
unaccompanied by some effort at developed argumentation, are
deemed waived."); Pabon, 819 F.3d at 33–34.
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B.
Rodriguez next attacks his revocation sentence on
procedural and substantive grounds. These challenges also fail.
We begin with procedural reasonableness. Rodriguez does
not direct our attention to any objection below that was
"sufficiently specific to call the district court's attention to
the asserted [procedural] error," as required to preserve for
appellate review an argument that a sentence is procedurally
unreasonable. United States v. Soto-Soto, 855 F.3d 445, 448 n.1
(1st Cir. 2017). We must therefore conclude that the argument was
not preserved, and is subject to plain error review. Because
Rodriguez does not attempt to satisfy that standard of review, his
procedural reasonableness argument is waived on appeal. Pabon,
819 F.3d at 33–34.3
In contrast, Rodriguez preserved his substantive
reasonableness challenge below by "advocat[ing] for a sentence
shorter than the one ultimately imposed." United States v. García-
Mojica, 955 F.3d 187, 194 (1st Cir. 2020) (quoting Holguin-
Hernandez v. United States, 140 S. Ct. 762, 766 (2020)). We
3 The crux of Rodriguez's procedural reasonableness claim
seems to be that the sentencing court disregarded his arguments
for leniency. We shortly return to -- and reject -- this
contention. Thus, even if Rodriguez had preserved his procedural
reasonableness claim before the sentencing court and had not waived
it on appeal, it would fail for the reasons discussed below.
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therefore review for abuse of discretion the substantive
reasonableness of the sentence. Id.A sentence is substantively reasonable if it rests on "a
plausible sentencing rationale" and reaches "a defensible result."
United States v. Cox, 851 F.3d 113, 120 (1st Cir. 2017) (quoting
United States v. Martin, 520 F.3d 87, 96 (1st Cir. 2008)). The
"universe of reasonable sentences" is "expansive." Id. (quoting
United States v. King, 741 F.3d 305, 308 (1st Cir. 2014)). And
"[w]e have repeatedly emphasized that '[a] challenge to the
substantive reasonableness of a sentence is particularly
unpromising when the sentence imposed comes within the confines of
a properly calculated [guideline range].'" Id. at 126 (second
alteration in original) (quoting United States v. Demers, 842 F.3d
8, 15 (1st Cir. 2016)).
Rodriguez's revocation sentence is substantively
reasonable. The district court imposed a sentence within (albeit
at the high end of) the probation officer's proffered guideline
range, and Rodriguez does not argue that the range was improperly
calculated. The district court also provided a plausible rationale
for the sentence when it explained that Rodriguez's "new criminal
conduct . . . has shown his serious disrespect for the law and his
lack of commitment to make changes towards a pro-social
reintegration into society." The court determined "that a sentence
at the high end of the guidelines [was] sufficient but not greater
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than necessary in this case" given Rodriguez's "noncompliance
history and characteristics."
On appeal, Rodriguez focuses on the district court's
failure to address potentially mitigating evidence, including his
"extremely difficult childhood," his learning disability, and his
responsibilities caring for his ailing mother. But this court
"do[es] not require an express weighing of mitigating and
aggravating factors or that each factor be individually
mentioned." United States v. Lozada-Aponte, 689 F.3d 791, 793
(1st Cir. 2012). We have upheld sentences imposed after the
district court "ha[s] read the defense's sentencing memo and ha[s]
heard the defense's leniency plea." United States v. Dávila-
Bonilla, 968 F.3d 1, 12 (1st Cir. 2020). That is precisely what
happened here. Further, the presentence investigation report --
which the court referenced before the revocation hearing --
described Rodriguez's childhood, his learning disability, and his
mother's ill health/medical needs. So the fact "that the district
court did not explicitly mention [mitigating factors] during the
sentencing hearing suggests they were unconvincing, not ignored."
Lozada-Aponte, 689 F.3d at 793.
III.
Rodriguez also raises a host of challenges to his
sentence on the section 922(g)(1) conviction for possessing
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ammunition. We begin with the question whether Rodriguez
effectively waived his right to appeal that sentence.
A.
Rodriguez's plea deal contained the following provision:
Defendant knowingly and voluntarily agrees
that, if the total term of imprisonment
imposed by the Court is 37 months or less, the
defendant waives the right to appeal any
aspect of this case's judgment and sentence,
including but not limited to the term of
imprisonment or probation, restitution,
fines, forfeiture, and the term and conditions
of supervised release.
Rodriguez signed the document containing this provision and, after
consulting with his lawyer off the record, confirmed he understood
that if the district court "sentence[d] [him] according to the
terms, conditions, and recommendations contained in [his] plea
agreement, [he] waive[d] and g[a]ve up [his] right to appeal [the]
sentence and the judgment in the case."
Rodriguez challenges his waiver as inadequate under
Federal Rule of Criminal Procedure 11(b)(1)(N), which requires a
district court to "inform the defendant of, and determine that the
defendant understands . . . the terms of any plea-agreement
provision waiving the right to appeal or to collaterally attack
the sentence." Because Rodriguez did not preserve any purported
Rule 11(b)(1)(N) error below, we consider his argument only on
plain error review. United States v. Morillo, 910 F.3d 1, 3 (1st
Cir. 2018). To satisfy that stringent standard, Rodriguez must
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demonstrate "(1) error, (2) that is plain, and (3) that affects
substantial rights." United States v. Borrero-Acevedo, 533 F.3d
11, 15 (1st Cir. 2008) (cleaned up) (quoting Johnson v. United
States, 520 U.S. 461, 467 (1997)). To satisfy the third prong of
this test, Rodriguez must "show a reasonable probability that, but
for the [Rule 11] error, he would not have entered the plea." Id.
at 16 (alteration in original) (quoting United States v. Dominguez
Benitez, 542 U.S. 74, 76 (2004)). If Rodriguez clears each of
these hurdles, we "may then exercise [our] discretion to notice
[the] forfeited error, but only if" the Rule 11 error "seriously
affect[s] the fairness, integrity, or public reputation of
judicial proceedings." Id. at 15 (third alteration in original)
(internal quotation marks omitted) (quoting Johnson, 520 U.S. at
467).
Rodriguez alleges that the district court failed to
confirm that he "freely, knowingly and intelligently waived his
right to appeal." Rodriguez claims "eight discrete" errors with
the court's inquiry: He argues that the court did not "explain
the [waiver's] ramifications"; explain its meaning "in plain
English"; explain that "the length of the sentence would be firm
and final"; "question[] the defendant about his understanding of
the waiver"; "ask[] the defendant if he had any questions about
the waiver"; "ask[] the defendant if anyone had forced or coerced
him to waive his right to appeal"; "advise[] the defendant
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that . . . he would be statutorily entitled to free counsel" if he
proceeded to trial and appeal; or "specifically ask[] [Rodriguez]
if he had discussed the appellate waiver with counsel."
Through his objections, Rodriguez effectively describes
his ideal plea colloquy. But while he is correct that
Rule 11(b)(1)(N) requires a district court to ascertain that a
defendant understands and freely accepts his plea waiver, we have
"refrain[ed] from prescribing any mandatory language for such an
inquiry" so long as "the court's interrogation [is] specific enough
to confirm the defendant's understanding of the waiver and [his]
acquiescence in the relinquishment of rights that it betokens."
United States v. Teeter, 257 F.3d 14, 24 n.7 (1st Cir. 2001).
None of Rodriguez's complaints about this colloquy rises
to the level of establishing error, plain or otherwise.
Rodriguez's colloquy was quite similar to the one we upheld under
a less deferential standard of review in United States v. De-La-
Cruz Castro, 299 F.3d 5 (1st Cir. 2002). In that case, the court
"asked Cruz Castro and his counsel if he knew 'that by entering
into this plea agreement and entering a plea of guilty [he] would
have waived or given up [his] right to appeal all or part of [his]
sentence,'" and "Cruz Castro answered, 'Yes, sir.'" Id. at 12(alterations in original). "The district court also determined
that Cruz Castro's counsel had 'explained this agreement to Cruz
Castro in Spanish and [was] satisfied that he [understood] it.'"
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Id. (alterations in original). We upheld the waiver in that case
despite the district court's "indicat[ion] that [the defendant]
could appeal 'in some circumstances,'" id. -- a potentially
confusing qualification not given here.
At Rodriguez's in-person change-of-plea hearing, the
prosecutor explained the plea agreement, including its "waiver of
appeal which indicates that the Defendant knowingly and
voluntarily agrees that if the total term of imprisonment is
37 months or less, the Defendant waives his right to appeal this
case's judgment." The court asked Rodriguez if he "agreed with
the [prosecutor's] summary" of the agreement, and Rodriguez said
"Yes." The court then confirmed that Rodriguez's counsel had
"explain[ed] the plea agreement" to Rodriguez "[w]ord for word"
"in Spanish," and that counsel was "satisfied that [Rodriguez]
underst[ood] it." Rodriguez then confirmed that he understood the
plea agreement's terms.
The court then asked Rodriguez whether he understood the
appellate waiver specifically. Rodriguez initially professed some
uncertainty and was permitted to consult with counsel off the
record. Afterward, Rodriguez confirmed that he understood that he
would "waive and give up [his] right to appeal [the] sentence and
the judgment in the case" if the judge sentenced him "according to
the terms, conditions, and recommendations contained in [the] plea
agreement." The court then ascertained that no one had "made any
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promise or assurance to . . . induce" Rodriguez to sign the plea
agreement, that no one had "attempted in any way to force" him to
do so, and that he was "pleading guilty of [his] own free will."
Most of Rodriguez's numerous challenges to the colloquy
boil down to one broad contention: that the court should have done
more to "explain to him, in plain English, what [the] waiver meant,
namely, the loss of appellate rights." But the court asked
Rodriguez: "[D]o you understand that if I sentence you according
to the terms, conditions, and recommendations contained in your
plea agreement, you waive and give up your right to appeal your
sentence and the judgment in the case?" We think this language is
sufficiently clear -- indeed, it is perhaps clearer than language
we have upheld in other cases. See, e.g., United States v.
González-Colón, 582 F.3d 124, 127 (1st Cir. 2009) ("Do you
understand that by pleading guilty, you will be held accountable
to the waiver of appeal clause that appears in your respective
plea agreements?"); United States v. Gil-Quezada, 445 F.3d 33, 37
(1st Cir. 2006) ("Do you understand that by entering into this
plea agreement you may have waived or given up your right to appeal
or collaterally attack all or part of the sentence?").
Beyond that, the court ensured that Rodriguez and his
counsel had reviewed the plea agreement "[w]ord for word" "in
Spanish" before Rodriguez signed it, and that Rodriguez had freely
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consented to the agreement. In short, we are satisfied that the
court did not plainly err in conducting its 11(b)(1)(N) inquiry.
B.
Finding that the district court did not plainly err in
performing its duties under Rule 11(b)(1)(N) does not quite end
our analysis. A valid appeal waiver does not necessarily prevent
us from averting a miscarriage of justice. Morillo, 910 F.3d at
3–4. And we have explained that, "[a]s a subset of this premise,"
we may "refuse to honor" a valid appeal waiver "when the district
court plainly errs in sentencing." Teeter, 257 F.3d at 25. So we
turn to the substance of Rodriguez's complaints about his
sentencing. We do so not to search again for error per se, but to
make sure that there is no error so "egregious" as to warrant
setting aside the valid appeal waiver. United States v. Goodman,
971 F.3d 16, 21 (1st Cir. 2020) (quoting United States v. Villodas-
Rosario, 901 F.3d 10, 18 (2018)).
Rodriguez argues that conducting his sentencing hearing
via videoconference was impermissible under Federal Rule of
Criminal Procedure 43 and the CARES Act notwithstanding his
consent.4 For the following reasons, we see no egregious error
here rising to the level of a miscarriage of justice.
Rodriguez also gestures at an ineffective assistance of
4
counsel claim, largely reprising the sparse argument discussed
above. It fails for the reasons already described.
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We begin with Rule 43. Federal Rule of Criminal
Procedure 43(c) provides that a defendant "who ha[s] pleaded
guilty . . . waives the right to be present" at sentencing when he
"is voluntarily absent during sentencing" "in a noncapital case."
A fortiori, it is by no means clear that a defendant could not opt
to appear by videoconference, rather than not at all as permitted
by the rule. In resisting this conclusion, Rodriguez points to
cases in which several of our sister circuits concluded that
Rule 43 does not permit sentencing via videoconference where the
defendant has not affirmatively consented to that format. See
United States v. Williams, 641 F.3d 758, 763–65 (6th Cir. 2011);
United States v. Torres-Palma, 290 F.3d 1244, 1245 (10th Cir.
2002); United States v. Lawrence, 248 F.3d 300, 302–05 (4th Cir.
2001); United States v. Navarro, 169 F.3d 228, 235 (5th Cir. 1999).
Because Rodriguez did affirmatively consent to videoconferencing,
those cases are inapposite. Also distinguishable is the Seventh
Circuit's decision United States v. Bethea, 888 F.3d 864 (7th Cir.
2018). In that case, the defendant argued that questions of
consent (or waiver) were irrelevant. See id. at 866. However, he
had not previously entered his plea in person, which the Seventh
Circuit determined was required under Rule 43. Id. at 867. Here,
Rodriguez entered his plea in person several months before his
sentencing videoconference. As a result, the Seventh Circuit's
reasoning in Bethea does not apply.
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Of course, even if videoconferencing were permissible
under Rule 43, it is possible that the CARES Act's apparently more
robust requirements for remote sentencing should govern. The CARES
Act permits sentencing via videoconference under certain public
health conditions related to COVID-19. § 15002(a)–(b), 134 Stat.
at 527–30. Even then, videoconferencing is permissible only if
the defendant consents "after consultation with counsel" and "the
district judge in a particular case finds for specific reasons
that the plea or sentencing in that case cannot be further delayed
without serious harm to the interests of justice." Id.
§ 15002(b)(2)(A), (4), 134 Stat. at 528–29. On appeal, Rodriguez
faults the district court for failing to conduct the interests-
of-justice analysis and for "failing to ask [him] if he had
conferred with counsel about his decision to waive his physical
presence."
As to the first contention, the parties agree that the
court did not (as required by the Act) offer any "specific reasons
that" Rodriguez's sentencing hearing could not "be further delayed
without serious harm to the interests of justice." CARES Act
§ 15002(b)(2)(A), 134 Stat. at 528–29.
As to the second contention, Rodriguez stops short of
claiming that he did not, in fact, confer with counsel prior to
waiving his right to appear in person -- rather, he complains that
"there is no proof he waived his physical presence at sentence
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only after conferring with counsel." Yet this claim is directly
contradicted by the pre-hearing filing in which Rodriguez
confirmed that he was consenting to videoconference "[a]fter
thorough discussion with his attorney." The court again addressed
the issue during the August 2020 proceedings. Shortly before
asking whether Rodriguez "wish[ed] to waive [his] right to appear
in person . . . and to appear instead by video," the district court
confirmed that Rodriguez understood he had "a right to consult
with [his] lawyer" before the sentencing and revocation hearings.
The court then asked Rodriguez's attorney if there was "any reason
why [it] should not accept" Rodriguez's waiver, and counsel said
he knew of none. The district court concluded that Rodriguez had
"knowingly and voluntarily waived his right to appear physically"
"after consulting with his attorney."
How to ultimately reconcile Rule 43 with the CARES Act,
we need not decide. Even if there was error here because the
district court failed to strictly comply with the CARES Act, such
error would not come close to making this an "egregious case[]"
triggering the miscarriage-of-justice exception to plain error
forfeiture. On these facts, neither the error nor its impact on
Rodriguez would be "grav[e]." González-Colón, 582 F.3d at 128(quoting Gil-Quezada, 445 F.3d at 37).
Nor does Rodriguez's use of the phrase "structural
defect" to describe this rather prosaic and relatively
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inconsequential procedural error change the equation. Structural
errors comprise a "tiny class," which "includes only the most
pervasive and debilitating errors" that "infect '[t]he entire
conduct of [a] trial from beginning to end.'" United States v.
Padilla, 415 F.3d 211, 219 (1st Cir. 2005) (en banc) (first
alteration in original) (quoting Arizona v. Fulminante, 499 U.S.
279, 309 (1991)). Here, proving structural error is an especially
daunting task: Because Rodriguez did not raise his claim below,
plain error review applies. United States v. Lara, 970 F.3d 68,
86 (1st Cir. 2020) ("The plain error standard of review
applies . . . even to challenges to structural errors if they were
not raised below." (citing Johnson, 520 U.S. at 466)), cert. denied
sub nom. Williams v. United States, 141 S. Ct. 2821 (2021).
Perhaps Rodriguez believes that the district court would
have been more receptive to his entreaties for leniency had he
appeared in person. But while we do not doubt the value of in-
person sentencing as a general matter, Rodriguez has failed to
persuade us that proceeding via videoconference during a global
pandemic with the express consent of a criminal defendant
constitutes error sufficiently grave to warrant setting aside an
otherwise valid appeal waiver.
C.
As to his sentence on the section 922(g)(1) conviction,
Rodriguez argues that the district court erred when it "failed to
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either explicitly or implicitly rule on appellant's motion for a
downward departure due to extraordinary family circumstances."
For its part, the government maintains that Rodriguez never made
such a motion.
Even assuming arguendo that Rodriguez's requests for
leniency constituted a motion for a downward departure, this
challenge fails. Rodriguez does not attempt to show that
sustaining the sentence would work a miscarriage of justice. As
a result, his claim cannot survive his valid appeal waiver.
D.
Rodriguez also alleges that his within-guideline-range
sentence was substantively unreasonable. But, once again,
Rodriguez fails to argue that sustaining the sentence would work
a miscarriage of justice. So his valid appeal waiver dooms this
claim as well.
E.
Finally, Rodriguez argues that the district court erred
by ordering him to "complete his high school education" as a
condition of supervised release included in his sentence on the
section 922(g)(1) conviction. Rodriguez's valid appeal wavier
covers conditions of supervised release, so we again consider
whether Rodriguez has demonstrated a miscarriage of justice.
Because we have suggested that plain sentencing error is "a subset"
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of the miscarriage-of-justice exception, Teeter, 257 F.3d at 25,
we use the two standards interchangeably in this analysis.
Rodriguez concedes that "[d]istrict courts have
significant flexibility to impose special conditions of supervised
release." United States v. Garrasteguy, 559 F.3d 34, 41 (1st Cir.
2009). Accordingly, he does not argue that a district court is
without authority to impose educational conditions of supervised
release. Nor does he dispute that educational opportunities can
"benefit [a] defendant so that . . . he's better equipped to not
re-commit crimes." Rather, he asserts that on the "unusual facts"
of his particular case, imposing a mandatory educational condition
was plain error. Rodriguez has a documented learning disability
and failed to complete the fourth grade on four separate occasions.
We are sympathetic to Rodriguez's claim that his liberty
should not be curtailed if he fails to "complete his high school
education" after a good-faith effort.5 And, given Rodriguez's
educational history, he may not be an ideal candidate for the sort
of mandatory educational requirement the district court imposed.
Cf. United States v. McKissic, 428 F.3d 719, 724 (7th Cir. 2005)
(opining that a requirement to complete high school was "especially
5 Rodriguez's stated "inten[tion] to use the [Bureau of
Prisons] to complete his education" and his request to serve his
sentence in a facility where he could pursue a GED suggest he will
make such a good-faith effort.
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suited to" the defendant, who had "nearly completed his high school
education"). That being said, Rodriguez expressed a desire to
continue his education while incarcerated, and nothing in the
record conclusively illustrates that he cannot find a way to
satisfy the court-imposed condition.
On the whole, we think it too soon to say more about
this issue given the limitations of our review. Rodriguez has
more than three years of his prison term yet to serve. Certainly
Rodriguez need try to complete a high school education. If he
succeeds, the better for everyone, and the issue disappears.
Conversely, should he fail, he can ask the district court to modify
the mandatory educational condition under Federal Rule of Criminal
Procedure 32.1(c).6 Should the district court deny his request,
Rodriguez can appeal that denial, and his challenge will be ripe
for our review. Cf. United States v. Davis, 242 F.3d 49, 51 (1st
Cir. 2001) (per curiam) (challenge was ripe where petitioner's
"term of supervised release [would] commence in less than two
months"); United States v. Medina, 779 F.3d 55, 67 (1st Cir. 2015)
(challenge was ripe where petitioner "could be subject to the
6 We have previously noted that "[t]he showing required for
a defendant to obtain a modification of a condition of supervised
release pursuant to [18 U.S.C. § 3583(e)] is an open question in
this circuit." Garrasteguy, 559 F.3d at 43 n.12. Whatever the
appropriate standard, we feel confident that it is less stringent
than the miscarriage-of-justice standard that governs our own
review in this appeal. See id. (comparing standards adopted by
two of our sister circuits).
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condition he challenges in the near term"). And the record at
that time will contain much more information, facilitating a more
informed evaluation of the condition's validity, likely under a
different standard than the one that controls our review of this
direct appeal of the imposition of the condition.
IV.
For the foregoing reasons, we affirm Rodriguez's
sentences.
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