Boston, MA - Criminal defense lawyer represented defendant with illegally distributing marijuana and of trafficking OxyContin charges.
This case concerns the
interpretation of a statutory bar in 8 U.S.C. § 1326(d) precluding
certain collateral attacks in criminal proceedings. Appellant
Jesus Leonardo Castillo-Martinez falls within the ambit of those
limitations for the reasons stated below. We affirm the district
court's denial of his motion to dismiss the criminal proceedings
Castillo-Martinez was removed to the Dominican Republic
in April 2013 after he was convicted in Massachusetts state court
of illegally distributing marijuana and in New Hampshire state
court of trafficking OxyContin. He illegally returned to the
United States and was arrested on August 20, 2016, on a Florida
fugitive warrant for a new controlled substances offense committed
in Florida. He was removed again on November 1, 2016.
On June 23, 2018, after illegally reentering the United
States again, he was arrested in Massachusetts once more on state
heroin trafficking charges. He was then federally indicted for
unlawfully reentering the United States in violation of 8 U.S.C.
§ 1326(a), which provides that "any alien who (1) has been . . .
deported, or removed or has departed the United States while an
order of exclusion, deportation, or removal is outstanding and
thereafter (2) enters, attempts to enter, or is at any time found
in, the United States . . . shall be fined under Title 18, or
imprisoned not more than 2 years, or both."
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Castillo-Martinez moved to dismiss the indictment under
8 U.S.C. § 1326(d), making two arguments that the element of
unlawful reentry was not satisfied because his original removal
order was not valid. First, he argued that his original removal
order in 2012 was defective because the Notice to Appear ("NTA")
he received did not include the time and place of his hearing.
Second, he argued that his removal order in 2012 was based on the
classification of his marijuana conviction as an aggravated
felony, a classification to which he said his immigration counsel
provided ineffective assistance by not objecting. He then argued
that the classification was improper under the Supreme Court's
later decision in Moncrieffe v. Holder, 569 U.S. 184 (2013), issued
after his removal order. As a result, he argued, the original
removal order must be declared invalid, and the criminal charges
for illegal reentry must be dismissed. The district court denied
Castillo-Martinez's motion. United States v. Castillo-Martinez,
378 F. Supp. 3d 46, 55 (D. Mass. 2019).
Castillo-Martinez was born in the Dominican Republic in
1973 and was admitted to the United States as a lawful permanent
resident in 1981. In 1996, he was convicted of violating Mass.
Gen. Laws ch. 94C, § 32C by "knowingly or intentionally
manufactur[ing], distribut[ing], dispens[ing] or cultivat[ing]"
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marijuana, a Class D substance under Massachusetts law. For this
crime, he received a suspended sentence and probation. See id.
§§ 31, 32C. He remained in the United States.
In February 2011, Castillo-Martinez was indicted by a
New Hampshire grand jury for conspiring to sell 15,000 tablets of
OxyContin for approximately $272,000 in violation of N.H. Rev.
Stat. Ann. § 318-B:2(I). While he was awaiting trial, U.S.
Immigration and Customs Enforcement ("ICE") lodged a detainer
against him. He was later convicted of the conspiracy charge in
June 2012 and received a suspended sentence and probation.1
Shortly after Castillo-Martinez's OxyContin conviction,
the Department of Homeland Security ("DHS") served him with an NTA
alleging that he was removable from the United States pursuant to
8 U.S.C. § 1227(a)(2)(A)(iii) because he had been convicted of an
aggravated felony. The NTA was based on Castillo-Martinez's 1996
marijuana conviction and did not state his OxyContin conviction as
its basis. The NTA did not state a specific date or time for
Castillo-Martinez's hearing and noted that they were "to be set."
Castillo-Martinez, acting through counsel, conceded
removability as alleged in the NTA under the law of the First
Circuit, which held that his marijuana conviction was an aggravated
1 Castillo-Martinez received a 576-day credit toward his
sentence for time served. That 576-day portion of his sentence
was not suspended.
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felony. Castillo-Martinez made the counseled choice to apply for
deferral of removal under the Convention Against Torture ("CAT").
He submitted affidavits in support of his CAT petition and
testified at an immigration hearing. On November 1, 2012, an
immigration judge ("IJ") denied him CAT relief and ordered that he
be removed to the Dominican Republic.2 Castillo-Martinez
unsuccessfully appealed this decision to the Board of Immigration
Appeals ("BIA") on March 13, 2013, and was removed to the Dominican
Republic on April 16, 2013. He did not challenge the BIA's
decision by seeking a petition for review.
Castillo-Martinez returned to the United States at some
point before April 28, 2016, when he was arrested in Florida on
another controlled substance charge. He fled Florida, and was
arrested on August 20, 2016, in Massachusetts pursuant to a
"Fugitive from Justice" warrant from Florida and was taken into
administrative custody by ICE. His removal order was reinstated,
and, on November 1, 2016, he was removed to the Dominican Republic.
2 The IJ issued a removal order for Castillo-Martinez,
which resulted in the execution of a "warrant of
removal/deportation." "We use the terms 'removal' and
'deportation' interchangeably in this opinion." United States v.
Luna, 436 F.3d 312, 314 n.1 (1st Cir. 2006). While 8 U.S.C.
§ 1326(d) refers to deportation orders, it encompasses the change
in name to removal orders. See United States v. Palomar-Santiago,
141 S. Ct. 1615, 1619 (2021) (applying 8 U.S.C. § 1326(d) to a
removal order); Padilla v. Kentucky, 559 U.S. 356, 364 n.6 (2010)
("The changes to our immigration law have also involved a change
in nomenclature; the statutory text now uses the term 'removal'
rather than 'deportation.'").
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Castillo-Martinez returned to the United States again.
On June 23, 2018, he was arrested in Massachusetts and charged
with trafficking heroin. On August 2, 2018, he was federally
indicted for unlawfully reentering the United States in violation
of 8 U.S.C. § 1326(a).
In February 2019, Castillo-Martinez moved to dismiss the
unlawful reentry charge. He made two arguments that the unlawful
reentry element of 8 U.S.C. § 1326(a) was not met because there
was no valid prior removal order. His first argument was that
there was no valid prior removal order because under the Supreme
Court's decision in Pereira v. Sessions, 138 S. Ct. 2105 (2018),
the fact that the NTA did not include a specific date or time
deprived the immigration court of jurisdiction and prevented it
from ordering his removal. His second argument was that there was
no valid prior removal order based on the Supreme Court's divided
decision in Moncrieffe, issued shortly after his removal. He
argued that under Moncrieffe, his marijuana conviction could not
serve as the basis for his 2012 removal order because that
conviction was not an aggravated felony, and further that his
counsel's failure to object on this basis amounted to ineffective
The government responded to Castillo-Martinez's two
arguments. As to the second argument, the government relied on
the statutory limitations on collateral attacks set forth in 8
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U.S.C. § 1326(d) and specifically argued that he did not fall
within any of the narrow exceptions that would have permitted a
collateral attack. Subsection 1326(d) states that in a criminal
proceeding under 8 U.S.C. § 1326(a), "an alien may not challenge
the validity of [a] deportation order . . . unless" the alien makes
three showings: (1) "the alien exhausted any administrative
remedies that may have been available to seek relief against the
order"; (2) "the deportation proceedings at which the order was
issued improperly deprived the alien of the opportunity for
judicial review"; and (3) "the entry of the order was fundamentally
unfair." 8 U.S.C. § 1326(d). The government argued that CastilloMartinez failed to exhaust his administrative remedies, that he
was not denied the opportunity for judicial review, and that the
removal proceedings were not fundamentally unfair.
The district court denied the motion. As to CastilloMartinez's first argument, relying on case law from other courts
of appeals, it held that the IJ had jurisdiction to issue a removal
order "[b]ecause Castillo-Martinez was served with an NTA
containing all of the required information and was presumably
served a separate Notice of Hearing informing him of the time and
place of his removal hearing (given that he actually appeared at
that hearing)." Castillo-Martinez, 378 F. Supp. 3d at 53; see
also Santos-Santos v. Barr, 917 F.3d 486, 490 (6th Cir. 2019);
Karingithi v. Whitaker, 913 F.3d 1158, 1162 (9th Cir. 2019).
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As to his second argument, the district court held that
Castillo-Martinez had not made the required showings necessary
under 8 U.S.C. § 1326(d) to collaterally attack the validity of
his original removal order. Castillo-Martinez, 378 F. Supp. 3d at
54. First, because Castillo-Martinez "concede[d] that he failed
to exhaust his administrative remedies and was not denied an
opportunity for judicial review," the court held that he had not
satisfied the first two § 1326(d) requirements. See id.; 8 U.S.C.
§ 1326(d)(1)-(2). Next, the court held that even if CastilloMartinez could be excused from meeting some of § 1326(d)'s
requirements if he could show his counsel had been ineffective, he
still could not prevail because he had not shown that his counsel's
performance was deficient or that he was prejudiced by either his
counsel's actions or the deportation order. Castillo-Martinez,
378 F. Supp. 3d at 54-55; see also 8 U.S.C. § 1326(d)(3) (requiring
a showing that "the entry of the [deportation] order was
fundamentally unfair" to collaterally attack it in a criminal
Castillo-Martinez pleaded guilty to the unlawful reentry
charge. He was sentenced to time served and a three-year term of
supervised release. He reserved the right to appeal the court's
denial of his motion to dismiss and timely exercised that right.
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We review de novo the legal conclusions underlying the
district court's denial of Castillo-Martinez's motion to dismiss.
See United States v. Mendoza, 963 F.3d 158, 161 (1st Cir. 2020),
cert. denied sub nom. Mendoza-Sanchez v. United States, 141 S. Ct.
834 (2020). We review its factual findings for clear error and
its "ultimate ruling" for abuse of discretion. See id. (quoting
United States v. Doe, 741 F.3d 217, 226 (1st Cir. 2013)). On
appeal, Castillo-Martinez renews the two main arguments he made to
the district court.
Castillo-Martinez's first argument, based on Pereira,
has already been considered and rejected by the First Circuit since
the district court's ruling. See Mendoza, 963 F.3d at 161 ("We
have already squarely rejected the contention that the omission of
the initial hearing date and time in a notice to appear deprives
the immigration court of jurisdiction over a removal
proceeding."); Goncalves Pontes v. Barr, 938 F.3d 1, 6-7 (1st Cir.
2019).3 It fails for this reason.
3 Castillo-Martinez submitted a Rule 28(j) letter saying
that the Supreme Court's recent decision in Niz-Chavez v. Garland,
141 S. Ct. 1474 (2021), supported his argument. Niz-Chavez dealt
with whether an NTA that did not include certain information
triggered the Illegal Immigration Reform and Immigrant
Responsibility Act's stop-time rule. See id. at 1479. The Court
described a "notice to appear" in a removal proceeding as a single
"case-initiating document," id. at 1482, but it did not suggest
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Castillo-Martinez's second argument is based on
Moncrieffe and his contention that he satisfies the conditions
under § 1326(d), which would permit him to collaterally attack his
prior removal. Subsection 1326(d) starts with a prohibition on
such collateral attacks, stating that in a § 1326(a) criminal
proceeding, "an alien may not challenge the validity of [a]
deportation order." The subsection then sets forth an exception
in an "unless" clause, providing that an alien may not bring a
collateral attack unless the alien satisfies three conditions:
(1) "the alien exhausted any administrative remedies that may have
been available to seek relief against the order"; (2) "the
deportation proceedings at which the order was issued improperly
deprived the alien of the opportunity for judicial review"; and
(3) "the entry of the order was fundamentally unfair." 8 U.S.C.
that a single-document NTA is also required to establish
jurisdiction. Thus, we remain bound by our holding in Mendoza
that "jurisdiction of an immigration court is governed by agency
regulation, not by [statute]. . . ." 963 F.3d at 161 (internal
citations omitted); see Maniar v. Garland, 998 F.3d 235, 242 & n.2
(5th Cir. 2021) (explaining that Niz-Chavez does not affect its
prior holding that an immigration court's jurisdiction is governed
by federal regulations and that an NTA without date or time
information is sufficient to confer jurisdiction).
4 Congress passed § 1326(d) with the intent of insulating
removal orders against collateral attacks in criminal proceedings,
emphasizing the importance of finality and deference to
immigration agency determinations while guaranteeing minimal due
process. See 140 Cong. Rec. S28440-41 (daily ed. Oct. 6, 1994)
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The district court was correct that Castillo-Martinez
has not met any of the three statutory requirements. He has not
exhausted the administrative remedies for his newly raised
ineffective assistance claim. Judicial review was plainly
available. The 2012 removal proceeding was not fundamentally
Castillo-Martinez fails to satisfy the first two
statutory requirements of § 1326(d). He neither exhausted his
administrative remedies nor was he deprived of an opportunity for
judicial review. As the Supreme Court recently emphasized, "each
of the statutory requirements of § 1326(d) is mandatory." United
States v. Palomar-Santiago, 141 S. Ct. 1615, 1622 (2021).
(statement of Sen. Smith) (stating that the language of § 1326(d)
"which is taken directly from the U.S. Supreme Court case of United
States v. Mendoza-Lopez, 481 U.S. 828 (1987), is intended to ensure
that minimum due process is followed in the original deportation
proceeding while preventing wholesale, time-consuming attack on
underlying deportation orders.").
In civil proceedings, a noncitizen who reenters the
United States illegally after having previously been ordered
removed may not challenge the original removal order at all if
that original order is reinstated. 8 U.S.C. § 1231(a)(5).
Subsection 1231(a)(5) provides that the reinstated order "is not
subject to being reopened or reviewed," and the noncitizen "is not
eligible and may not apply for any relief" from the order. Id.
Subsection 1231(a)(5) underscores the importance of the finality
of a removal order once entered. There is no reason to think that
Congress intended a lesser degree of finality in criminal cases
than in civil cases.
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We may affirm a district court's decision based on any
independent ground supported by the record, even if the district
court did not reach the issue. See United States v. Cabrera-Polo,
376 F.3d 29, 31 (1st Cir. 2004) ("We are not committed to the
district court's reasoning, but, rather, may affirm its order on
any independent ground made apparent by the record."); see also
Dimott v. United States, 881 F.3d 232, 238-40 (1st Cir. 2018).
Castillo-Martinez conceded that he has not met the first
two § 1326(d) requirements in the traditional sense. See CastilloMartinez, 378 F. Supp. 3d at 54. The Supreme Court issued its
decision in Moncrieffe on April 23, 2013, shortly after CastilloMartinez's first removal. Between April 2013 and February 2019,
when he moved to dismiss the unlawful reentry charge, CastilloMartinez never once filed a motion to reopen his 2012 removal
proceedings based on ineffective assistance of counsel in light of
Moncrieffe. See 8 U.S.C. § 1229a(c)(7).5
We have long recognized the exhaustion requirement as an
important element of the § 1326(d) requirements for an alien to
collaterally attack a removal order. See United States v. Luna,
436 F.3d 312, 317 (1st Cir. 2006). This exhaustion requirement is
5 Motions to reopen removal hearings are disfavored
because of "the compelling public interests in finality and the
expeditious processing of proceedings." Muyubisnay-Cungachi v.
Holder, 734 F.3d 66, 71 (1st Cir. 2013) (quoting Raza v. Gonzales,
484 F.3d 125, 127 (1st Cir. 2007)).
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consistent with the congressional intent underlying § 1326(d) to
defer to agency determinations and restrict collateral attacks on
those agency determinations.
Castillo-Martinez nevertheless argues that if he can
show that his counsel was ineffective, we should excuse his failure
even where he failed to exhaust his ineffective assistance claim
before the BIA. We do not accept his proposition, though we
acknowledge that some circuits adopted this approach before the
Supreme Court's recent decision in Palomar-Santiago. See United
States v. Lopez-Chavez, 757 F.3d 1033, 1044 (9th Cir. 2014)
(holding that the first two § 1326(d) requirements were satisfied
because "counsel's ineffectiveness . . . caused [defendant's]
failure to exhaust administrative remedies and deprived him of his
opportunity for judicial review"); United States v. Cerna, 603
F.3d 32, 40 (2d Cir. 2010) (holding that ineffective assistance of
counsel may be grounds to excuse § 1326(d)(2)'s requirement).
The text of § 1326(d) and the Supreme Court's decision
in Palomar-Santiago do not support excusing Castillo-Martinez's
failure to satisfy the statutory requirements. In PalomarSantiago, the unanimous Court answered the statutory question
before it by holding that the "first two procedural requirements
are not satisfied just because a noncitizen was removed for an
offense that did not in fact render him removable." PalomarSantiago, 141 S. Ct. at 1621. The Ninth Circuit's contrary holding
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was "incompatible with the text of § 1326(d)." Id. at 1620. The
Court held that "[w]hen Congress uses 'mandatory language' in an
administrative exhaustion provision, 'a court may not excuse a
failure to exhaust.'" Id. at 1621 (quoting Ross v. Blake, 136 S.
Ct. 1850, 1857 (2016)) (emphasis added). That is exactly what
Castillo-Martinez asks us to do. He concedes that he has not met
the first two § 1326(d) requirements but asks us to excuse those
failures. See Ross, 136 S. Ct. at 1856 (holding that, other than
the requirement that a remedy be "available," the text of the
Prison Litigation Reform Act ("PLRA") "suggests no limits on an
inmate's obligation to exhaust -- irrespective of any 'special
The Supreme Court rejected Palomar-Santiago's
counterargument that he should be excused from showing the first
two procedural requirements of § 1326(d) because further
administrative review of a removal was not "available" when the IJ
erroneously informed him that his prior conviction rendered him
removable. Palomar-Santiago, 141 S. Ct. at 1621 ("Noncitizens,
the argument goes, cannot be expected to know that the immigration
judge might be wrong."). The Court found that administrative
review and judicial review of the removal were not "unavailable."
Id. The Court reasoned that "[a]dministrative review of removal
orders exists precisely so noncitizens can challenge the substance
of immigration judges' decisions." Id. The Court further stated
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that "[t]he immigration judge's error on the merits does not excuse
the noncitizen's failure to comply with a mandatory exhaustion
requirement if further administrative review, and then judicial
review if necessary, could fix that very error." Id.
This reasoning applies equally to Castillo-Martinez.
The BIA "provides a process for adjudicating ineffective
assistance of counsel claims through a motion to reopen."
Gicharu v. Carr, 983 F.3d 13, 17 (1st Cir. 2020). CastilloMartinez does not explain why he never moved to reopen his removal
proceedings after Moncrieffe. The ninety-day deadline for filing
such a motion, see 8 C.F.R. § 1003.23(b)(1), does not render relief
via a motion to reopen unavailable. As this court has previously
explained, "[t]he BIA . . . entertains claims for equitable tolling
of the filing deadline for motions to reopen where it is alleged
that ineffective assistance of counsel caused the motion to be
untimely." Gicharu, 983 F.3d at 17 (citing Pineda v. Whitaker,
908 F.3d 836, 840-41 (1st Cir. 2018)). Even if "the standard for
establishing equitable tolling is daunting, it does not render
review by the BIA . . . unavailable." Id. at 18 (internal citation
omitted); cf. Ross, 136 S. Ct. at 1858 (explaining that the PLRA's
exhaustion requirement "hinges on the 'availab[ility]' of
administrative remedies" because "[a]n inmate . . . must exhaust
available remedies but need not exhaust unavailable ones").
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Ordinarily, an alien raising an ineffective assistance
of counsel claim through a motion to reopen must comply with the
procedural requirements set forth in the leading BIA case Matter
of Lozada, 19 I. & N. Dec. 637 (BIA 1988):
(1) an affidavit explaining the petitioner's
agreement with counsel regarding legal
representation; (2) evidence that counsel has
been informed of the allegations of
ineffective assistance and has had an
opportunity to respond; and (3) if it is
asserted that counsel's handling of the case
involved a violation of ethical or legal
responsibilities, a complaint against the
attorney filed with disciplinary authorities
or, in the alternative, an explanation for why
such a complaint has not been filed.
Ferreira v. Barr, 939 F.3d 44, 46 (1st Cir. 2019) (quoting Pineda,
908 F.3d at 839 n.2); see Lozada, 19 I. & N. Dec. at 639; see also
Pineda, 908 F.3d at 839 n.2 ("The BIA's decision in Lozada is
widely recognized as a leading case with respect to claims of
ineffective assistance of counsel in the immigration context.").
We have recognized that the Lozada requirements are "designed to
give the BIA sufficient information to inform its decision without
resorting to an evidentiary hearing." Ferreira, 939 F.3d at 46.
In the BIA's view, false claims of ineffective assistance can be
identified by a counsel's response to the notification or the
alien's insufficiently explained refusal to file a formal
complaint against that counsel. Saakian v. INS, 252 F.3d 21, 26
(1st Cir. 2001). These requirements lessen the chances of
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meritless claims and make it easier for the BIA to act on
meritorious claims of ineffective assistance. Id.
Once the procedural requirements are satisfied, the BIA
reviews ineffective assistance claims for two substantive
requirements: (1) immigration counsel's performance was deficient;
and (2) immigration counsel's performance caused prejudice to the
client. See Matter of Melgar, 28 I. & N. Dec. 169, 171 (BIA 2020);
Lozada, 19 I. & N. Dec. at 638.
After the BIA issues its decision, an alien may then
file a petition for review with our court. When reviewing the
BIA's decisions, we uphold findings of fact about ineffective
assistance "as long as they are supported by substantial evidence
on the record as a whole." Ferreira, 939 F.3d at 45. We review
the BIA's denial of a motion to reopen for ineffective assistance
for abuse of discretion. Muyubisnay-Cungachi v. Holder, 734 F.3d
66, 70 (1st Cir. 2013).
Castillo-Martinez and the dissent would have us bypass
this process entirely and in doing so, alter our standard of review
from the substantial evidence standard to de novo review of
fundamental fairness concerns. The dissent's approach would have
us decide de novo, without record support, whether counsel's
conduct constituted ineffective assistance. Subsection 1326(d)
does not allow for this. The ability to assert an ineffective
assistance of counsel claim to the BIA was available to Castillo-
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Martinez well before his February 2019 motion to dismiss his
unlawful reentry charge. He failed to exhaust any such claim
before the agency.
Even assuming dubitante that Castillo-Martinez can
satisfy § 1326(d)'s first two requirements despite his failure to
move to reopen his removal proceedings or assert an ineffective
assistance claim to the agency, he has not shown that "the entry
of the order was fundamentally unfair." 8 U.S.C. § 1326(d)(3).
Castillo-Martinez argues that he can satisfy this third
requirement of § 1326(d) by demonstrating ineffective assistance
of counsel, but he has not met his burden of showing that his
immigration counsel was ineffective on the record before us.
Aliens in removal proceedings are not defendants in
criminal proceedings. The same rules do not apply. See Ferreira,
939 F.3d at 46 n.1. For example, aliens in removal proceedings
have no Sixth Amendment right to counsel. See id.; Saakian, 252
F.3d at 24. In his removal proceeding, Castillo-Martinez sought
a benefit from the government: to remain in the country. The
proceeding was not to determine whether his liberty would be
involuntarily restrained; indeed, he remained free to depart on
his own at any time. It is true that under Reno v. Flores, removal
proceedings must comport with the fundamental requirements of the
Due Process Clause under the Fifth Amendment. 507 U.S. 292, 306
- 19 -
(1993). Accordingly, his burden of showing ineffective assistance
of counsel in his removal proceeding is different than the burden
put on criminal defendants under Strickland. Cf. Strickland v.
Washington, 466 U.S. 668, 687 (1984). We have held that
"[i]neffective assistance of counsel in a deportation proceeding
is a denial of due process under the Fifth Amendment if the
proceeding was so fundamentally unfair that the alien was prevented
from reasonably presenting his case." Fustaguio Do Nascimento v.
Mukasey, 549 F.3d 12, 17 (1st Cir. 2008) (quoting Rodríguez–
Lariz v. INS, 282 F.3d 1218, 1226 (9th Cir. 2002)). To establish
that a proceeding was fundamentally unfair because of ineffective
assistance of immigration counsel, an alien must show " a
deficient performance by counsel and  'a reasonable probability
of prejudice resulting from [his] former representation.'"
Muyubisnay-Cungachi, 734 F.3d at 72 (quoting Zeru v. Gonzales, 503
F.3d 59, 72 (1st Cir. 2007)).
Castillo-Martinez cannot meet that standard before the
BIA, nor can he meet that standard before this court.
Even on review of the record before us, CastilloMartinez has not shown that his counsel at the removal proceeding
was deficient. Castillo-Martinez argues that his counsel "was
ineffective in conceding that Castillo-Martinez's marijuana
offense qualified as an aggravated felony." His counsel's
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strategic concession was based on longstanding and controlling
First Circuit precedent. See Julce v. Mukasey, 530 F.3d 30, 35
(1st Cir. 2008), abrogated by Moncrieffe, 569 U.S. at 187. Absent
"unusual circumstances," "the case law is clear that an attorney's
assistance is not rendered ineffective because he failed to
anticipate a new rule of law." Powell v. United States, 430 F.3d
490, 491 (1st Cir. 2005) (quoting Kornahrens v. Evatt, 66 F.3d
1350, 1360 (4th Cir. 1995)).
Any ineffective assistance of counsel claim is also
defeated by the fact that Castillo-Martinez's counsel had
strategic reasons for conceding removability. In addition to the
marijuana conviction, Castillo-Martinez was convicted of
conspiracy to sell OxyContin under N.H. Rev. Stat. Ann. § 318-
B:2(I) before the government sent him an NTA. This conviction
qualifies as an aggravated felony and would have provided a
standalone basis for mandatory removal. See 8 U.S.C. § 1227(a);
id. § 1227(a)(2)(A)(iii).6 Castillo-Martinez's counsel may have
6 To decide if a state conviction qualifies as an
aggravated felony under the Immigration and Nationality Act
("INA"), we "employ a 'categorical approach' to determine whether
the state offense is comparable to an offense listed in the INA."
Moncrieffe, 569 U.S. at 190. Under this approach, we determine if
"'the state statute defining the crime of conviction'
categorically fits within the 'generic' federal definition of a
corresponding aggravated felony." Id. at 190 (quoting Gonzales v.
Duenas-Alvarez, 549 U.S. 183, 186 (2007)).
Under the INA, an aggravated felony includes "illicit
trafficking in a controlled substance (as defined in [21 U.S.C. §
802]), including a drug trafficking crime (as defined in [18 U.S.C.
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correctly concluded that even after predicting the Supreme Court
would overturn controlling First Circuit precedent in Moncrieffe,
any objection on this basis would be futile given Castillo-
§ 924(c)]." 8 U.S.C. § 1101(a)(43)(B). A drug trafficking crime
is "any felony punishable under the Controlled Substances Act
[("CSA")]." 18 U.S.C. § 924(c)(2). Under the CSA, it is a felony
"to manufacture, distribute, or dispense, or possess with intent
to manufacture, distribute, or dispense, a controlled substance,"
21 U.S.C. § 841(a)(1), if the "maximum term of imprisonment
authorized" is more than one year, 18 U.S.C. § 3559(a)(5); see
Moncrieffe, 569 U.S. at 188.
In United States v. Burghardt, 939 F.3d 397, 406-09 (1st
Cir. 2019), applying the categorical approach, this court held
that because the elements of selling a controlled substance under
N.H. Rev. Stat. Ann. § 318-B:2(I) were not broader than the
elements of the generic "serious drug offense" defined in the Armed
Career Criminal Act, a § 318-B:2(I) conviction for selling drugs
is a "serious drug offense." Id. A "serious drug offense"
includes "an offense under State law, involving manufacturing,
distributing, or possessing with intent to manufacture or
distribute, a controlled substance (as defined in [21 U.S.C.
§ 802]), for which a maximum term of imprisonment of ten years or
more is prescribed by law." 18 U.S.C. § 924(e)(2)(A)(ii).
As is clear from their respective definitions, serious
drug offenses under 18 U.S.C. § 924(e)(2)(A)(ii) are a subset of
drug trafficking crimes as defined by 18 U.S.C. § 924(c). This
means that a serious drug offense is necessarily a drug trafficking
crime, and a drug trafficking crime is necessarily an aggravated
felony. It follows that Castillo-Martinez's § 318-B:2(I)
conviction is an aggravated felony under the INA and would have
precluded him from receiving various types of discretionary relief
from the removal order. See United States v. Hercules, 947 F.3d
3, 8 (1st Cir. 2020) (stating that "appellant's aggravated felony
convictions render him ineligible for various forms of relief from
removal," including cancellation of removal, 8 U.S.C.
§ 1229b(a)(3), and asylum, id. § 1158(b)(2)(A)(ii), (B)(i)).
Castillo-Martinez was convicted of conspiracy to sell OxyContin,
but "conspiracy to commit an offense described in [8 U.S.C. §
1101(a)(43)]" is also an aggravated felony. 8 U.S.C. §
- 22 -
Martinez's other drug conviction. See Knowles v. Mirzayance, 556
U.S. 111, 126-27 (2009).
That counsel was making a strategic choice is shown by
the fact that Castillo-Martinez applied for deferral of removal
under the CAT and submitted affidavits and testimony from himself
and his sister in support. Castillo-Martinez's counsel was not
deficient because he elected to focus on one defense to removal
rather than another defense that he reasonably perceived as weak.
This is not a case where counsel gave up "the only defense
available." Knowles, 556 U.S. at 126-27 ("Counsel also is not
required to have a tactical reason . . . for recommending that a
weak claim be dropped altogether.").7
7 There was a second strategic choice involved. An alien
previously ordered removed because of an aggravated felony
conviction is not eligible to seek readmission for 20 years. See
8 U.S.C. § 1182(a)(9)(A)(i); 8 C.F.R. § 212.2(a). Prior to the
completion of the 20-year absence, an alien may apply for a
discretionary I-212 waiver, or "permission to reapply." See 8
U.S.C. § 1182(d)(3); 8 C.F.R. §§ 212.2(a), 212.4. Counsel could
have easily concluded that Castillo-Martinez would be removed
based on either drug conviction. Had counsel objected to the
marijuana conviction as the basis for the removal order or
requested a stay pending the Supreme Court's decision in
Moncrieffe, this would have only prolonged the removal
proceedings. Counsel did not know when the Supreme Court would
issue its decision in Moncrieffe, and the government could have
amended the NTA to include the Oxycontin conviction, thus
prolonging the removal proceedings further. See 8 C.F.R.
§ 1240.10(e). Any delay in removal would also delay the running
of Castillo-Martinez's 20-year absence requirement.
- 23 -
Castillo-Martinez also cannot show prejudice resulting
from his immigration counsel's actions. See Muyubisnay-Cungachi,
734 F.3d at 72.
Even if Castillo-Martinez's marijuana conviction had not
been classified as an aggravated felony, he has failed to show
that there is a reasonable probability he would not have been
removed because of that conviction. As a controlled substance
offender under 8 U.S.C. § 1227(a)(2)(B)(i), he would have had to
apply for and receive discretionary relief to avoid deportation.
See Moncrieffe, 569 U.S. at 204 (2013) ("Escaping aggravated felony
treatment does not mean escaping deportation . . . It means only
avoiding mandatory removal."); United States v. Soto-Mateo, 799
F.3d 117, 123 (1st Cir. 2015) (explaining that "even if the
appellant's prior convictions did not comprise aggravated
felonies, he would not have been entitled as of right to remain in
the United States" and holding that there is no "constitutional
right to be . . . considered for . . . discretionary relief"); 8
U.S.C. § 1229b(a). Castillo-Martinez has made no argument that he
would have applied for such discretionary relief, let alone has he
offered any affirmative reasons why that relief would have been
warranted. His drug convictions prior to the entry of his
deportation order and "the relative lack of positive equities
- 24 -
eliminate any reasonable likelihood that he would have received a
grant of relief." Luna, 436 F.3d at 323.
Castillo-Martinez also has not shown that he would not
have been subject to mandatory removal because of his separate
OxyContin conviction. Even if he had successfully challenged the
earlier aggravated felony classification for his Massachusetts
offense, the government could have freely amended the NTA to
include other grounds for removal. Federal regulations say that
"[a]t any time during the proceeding" the government may lodge
"additional or substituted charges of inadmissibility and/or
deportability and/or factual allegations." 8 C.F.R. § 1240.10(e).
"[T]here is no requirement that the [government] advance every
conceivable basis for deportability" in the original NTA.
Magasouba v. Mukasey, 543 F.3d 13, 16 (1st Cir. 2008) (per curiam)
(second alteration in original) (quoting De Faria v. INS, 13 F.3d
422, 424 (1st Cir. 1993) (per curiam)). The government is also
allowed to replace all of the original charges in the NTA with new
ones, see Cheung v. Holder, 678 F.3d 66, 70 n.6, 70-71 (1st Cir.
2012), and "reopen . . . deportation proceedings to consider . . .
substitute charges" against an alien if the convictions underlying
the original charges have been vacated, De Faria, 13 F.3d at 424.
Castillo-Martinez fails to satisfy the distinct
statutory prejudice requirement under § 1326(d)(3), which
- 25 -
separately requires a "showing of prejudice." Soto-Mateo, 799
F.3d at 124. "[S]uch a showing entails 'a reasonable likelihood
that the result would have been different if the error in the
deportation proceeding had not occurred.'" Id. (quoting Luna, 436
F.3d at 321).
Castillo-Martinez argues that the district court's
prejudice analysis is incorrect because we must focus only on the
basis for removal cited in his original NTA for his 2012 removal
order. He says that because his NTA included only his marijuana
conviction and specifically said it was an aggravated felony under
8 U.S.C. § 1227(a)(2)(A)(iii), "[o]ther grounds for removal are
not relevant to the instant question of prejudice."8
We review whether entry of the removal order was
fundamentally unfair. See United States v. Martinez-Hernandez,
8 In support of this argument, Castillo-Martinez cites
SEC v. Chenery Corp., 332 U.S. 194, 196 (1947), which says we are
"powerless to affirm the administrative action by substituting
what [we] consider to be a more adequate or proper basis." He
also cites cases from the Ninth Circuit supporting his
understanding of the prejudice analysis. See, e.g., United
States v. Camacho-Lopez, 450 F.3d 928, 930 (9th Cir. 2006)
("[Defendant's] Notice to Appear charged him as removable only for
having committed an aggravated felony . . . [because his] prior
conviction did not fit that definition[, he] was removed when he
should not have been and clearly suffered prejudice.").
Chenery is inapposite because we are not affirming his
removal order or the basis for its entry. We are reviewing the
district court's rejection of his collateral attack on the order
and considering whether entry of the deportation order was
fundamentally unfair. See United States v. Martinez-Hernandez,
932 F.3d 1198, 1204 (9th Cir. 2019).
- 26 -
932 F.3d 1198, 1204 (9th Cir. 2019). In doing so, we must consider
other grounds available to the government that would also have
supported entry of the removal order. We assess then the chances
of Castillo-Martinez receiving relief from removal. See United
States v. Almanza-Vigil, 912 F.3d 1310, 1323 n.10 (10th Cir. 2019)
(explaining that 8 U.S.C. § 1326(d)(3) "prohibits us from
addressing the removal order itself unless [the defendant] can
establish that the order's entry was fundamentally unfair," and
"the fundamental-unfairness inquiry hinges on [the defendant's]
chances of receiving relief from removal"). We assess CastilloMartinez's chances of relief from removal as a key part of the due
process fundamental unfairness inquiry embodied in the statutory
bar to such collateral attacks. Here, Castillo-Martinez's chances
of relief from removal were nonexistent. His outstanding New
Hampshire Oxycontin conviction was not a small offense. He
conspired to distribute more than 15,000 OxyContin tablets for
over $270,000. He was a dealer of a drug plaguing New Hampshire.
It is inconceivable that the government would not have amended his
removal order to add the more serious OxyContin conviction if the
marijuana conviction could not serve as a basis for removal.
We respond below in greater detail to the dissent.9
9 We note at the outset that the government did not waive
its arguments as to whether Castillo-Martinez satisfied the first
- 27 -
The dissent objects to our consideration that CastilloMartinez's counsel made a strategic choice not to object and to
instead apply for deferral of removal under the CAT. The dissent
states that Castillo-Martinez "was not apprised at any prior point
in the litigation that [this ground] was even in dispute." But it
is Castillo-Martinez who bears the burden of demonstrating that
his immigration counsel provided assistance so ineffective as to
violate the Constitution. He has the burden as to the totality of
two statutory requirements of § 1326(d). In the district court,
the government argued that Castillo-Martinez both failed to
exhaust his administrative remedies and that he was not denied the
opportunity for judicial review. On appeal, the government
maintains the same position and argues that our circuit has not
recognized an exception to the statutory exhaustion requirement
and need not do so in this case. The government's brief continues
with language that deliberately does not concede these arguments:
"Even assuming such an exception exists, Castillo-Martinez has not
established that he would be entitled to it." An "assuming
arguendo" statement is not a concession and not a waiver.
Waiver is "treated as an 'intentional,' and therefore
permanent, abandonment of a position." United States v. TorresRosario, 658 F.3d 110, 115 (1st Cir. 2011) (quoting United
States v. Walker, 538 F.3d 21, 22 (1st Cir. 2008)). There was no
intentional abandonment by the government here. As such, there
was no waiver.
Further, even if there had been a waiver, we do not
"'religiously' hold waiver against the Government" where the
government focuses its argument on one procedural bar rather than
another. Dimott, 881 F.3d at 238-40 (holding that federal courts
may raise sua sponte procedural arguments not raised by the
government). "[W]e have discretion to overlook waiver by the
government in a criminal case when circumstances justify us in
doing so." United States v. Carrasco-De-Jesús, 589 F.3d 22, 26
n.1 (1st Cir. 2009); see United States v. Borrero-Acevedo, 533
F.3d 11, 15 n.3 (1st Cir. 2008) ("This court is not bound by a
- 28 -
his counsel's actions in the immigration proceedings. See
Muyubisnay-Cungachi, 734 F.3d at 72. Castillo-Martinez had
numerous opportunities to address this ground, including by
raising the issue of ineffective assistance before the
administrative agency, which he failed to do.
The dissent also misunderstands the scope of our review
under 8 U.S.C. § 1326(d). Congress did not adopt the dissent's
reading of United States v. Mendoza-Lopez, 481 U.S. 828 (1987), in
passing § 1326(d). Rather, § 1326(d) makes clear that CastilloMartinez "may not challenge the validity of the deportation order"
unless he first demonstrates that "the entry of the order was
fundamentally unfair." 8 U.S.C. § 1326(d). When Congress used
the phrase "fundamentally unfair" in § 1326(d)(3), it meant that
aliens must show that they have been denied due process under the
Fifth Amendment. See United States v. Torres, 383 F.3d 92, 103
(3d Cir. 2004) (collecting cases and noting that "[i]n measuring
whether an alien's removal proceeding was 'fundamentally unfair,'
most circuits ask whether the alien was denied due process"). To
establish a due process violation, an alien must show both
procedural error and prejudice.10 See Luna, 436 F.3d at 319
10 We have recognized that "[t]here may be some cases where
the agency's violation of a petitioner's rights was 'so flagrant,
and the difficulty of proving prejudice so great' that prejudice
may be presumed." Luna, 436 F.3d at 321 n.14 (quoting United
States v. Loaisiga, 104 F.3d 484, 488 (1st Cir. 1997)). Those
circumstances would be akin to structural errors in the criminal
- 29 -
("[C]ourts uniformly require a showing of procedural error and
prejudice" under §1326(d)(3)); cf. United States v. Marcus, 560
U.S. 258, 264-5 (2010) (explaining in the criminal context that
the Court has "insisted upon a showing of individual prejudice"
for a claim of non-structural error under the Due Process Clause);
Strickland, 466 U.S. at 696 (stating that ineffective assistance
claims under the Sixth Amendment require a showing of deficient
performance and prejudice and that "the ultimate focus of inquiry
must be on the fundamental fairness of the proceeding whose result
is being challenged."). Interpreting § 1326(d)'s "fundamentally
unfair" language to require a due process violation is consistent
with Congress's goal of making it more difficult for aliens to
collaterally attack their removal orders. See H.R. Rep. No. 104-
22, at 16 (1995) (noting that the Criminal Alien Deportation
Improvements Act "amends the INA to provide that the alien charged
with [illegal reentry] may only challenge the validity of the
original deportation order" if § 1326(d)'s conditions are met).
The dissent misreads the significance of the definite
article "the" and in doing so, renders the two separate prejudice
requirements, under the ineffective assistance standard and the
§ 1326(d) fundamental unfairness standard, meaningless. Under the
context. See Weaver v. Massachusetts, 137 S. Ct. 1899, 1905 (2017)
(describing a "structural error" as "an error entitling the
defendant to automatic reversal without any inquiry into
prejudice"). That is not this case.
- 30 -
dissent's approach, we would be limited to looking at the basis of
the original order and not any other grounds for removal that would
have supported entry of the removal order.11 This interpretation
of § 1326(d) could be satisfied by the showing of any error in the
original order, thereby reading out both prejudice requirements
The dissent's prejudice conclusion also improperly
focuses on the specific ground for the removal order rather than
looking at the entire context of the removal proceeding. In
criminal proceedings, the prejudice analysis requires that a
defendant show that "[i]t must be reasonably likely that the result
of the criminal proceeding would have been different if counsel
had performed as the defendant asserts he should have." Rivera11 Even if we were limited to Castillo-Martinez's original
removal order, the IJ acknowledged Castillo-Martinez's Oxycontin
conviction and recognized that it would serve as a basis for
mandatory removal. The IJ wrote in that removal order:
The Respondent has criminal convictions from
1996 for the Manufacture, Distribution, and
Cultivation of Marijuana, for which he
received a sentence of two years in a house of
corrections. This is an aggravated felony,
which comprises the basis for removal. In
addition, more recently, the Respondent was
convicted this year for a 2010 violation in
Rockingham, New Hampshire, for Possession and
Sale of a Narcotic Drug and the Conspiracy
Thereof, for which he received again a two
year suspended sentence. This, too, is a drug
trafficking offense constituting an
- 31 -
Rivera v. United States, 827 F.3d 184, 187 (1st Cir. 2016)
(quotations omitted). "[T]hat likelihood 'must be substantial,
not just conceivable.'" Hensley v. Roden, 755 F.3d 724, 736 (1st
Cir. 2014) (quoting Harrington v. Richter, 562 U.S. 86, 112
(2011)). Here, Castillo-Martinez has not shown that there is a
substantial likelihood that the result of the removal proceeding
would have been different. The IJ in Castillo-Martinez's original
removal order specifically acknowledged that the OxyContin
conviction "too, is a drug trafficking offense constituting an
aggravated felony." Even if Castillo-Martinez's marijuana
conviction had not been classified as an aggravated felony, the
result of the proceeding would have been the same -- a removal
order -- even if the ground supporting the entry of that removal
order may have been different.
Our holding in Williams v. United States, 858 F.3d 708,
716 (1st Cir. 2017), is instructive as to the scope of the
applicable prejudice analysis. In that case, Williams was charged
in New Hampshire under 18 U.S.C. § 1542 for committing passport
fraud. New Hampshire was an improper venue for this charge but a
proper venue for the related, uncharged offense of making a
material false statement in violation of 18 U.S.C. § 1001.
Williams told his counsel that he "wanted the case to be dismissed"
because venue was improper. Id. at 712. Instead, his counsel
consented to the government's filing of a superseding indictment
- 32 -
replacing the § 1542 charge with a charge under § 1001. Williams
eventually pleaded guilty to the § 1001 charge in New Hampshire,
but he argued that, but-for his counsel's concession, the
government would have had to bring a new charge and he could have
transferred the case to his hometown in New York instead of being
forced to defend it in New Hampshire. Id. at 716. Specifically,
he argued that "the initial result of the proceeding would have
been different because the § 1542 charge for passport fraud would
have been dismissed." Id.
In conducting the prejudice analysis, we did not focus
narrowly on whether the original charge against Williams would
have been dismissed (as Castillo-Martinez would have us do here).
Instead, we focused more broadly on the likely result of the
proceeding, holding that it "would have been no different had his
counsel not agreed with the government's wish to file a superseding
indictment" because he would have eventually been charged and
convicted under § 1001 in either New Hampshire or New York, even
if the government would have had to file new charges in a new
indictment. Id. So too here: Castillo-Martinez cannot show
prejudice because, regardless of whether his counsel had asked the
court to delay the proceedings pending Moncrieffe, it is likely a
removal order would have been entered against him.
The dissent, in several ways, is inconsistent with the
congressional intent underlying § 1326(d). First, the dissent's
- 33 -
reading eliminates the exhaustion requirement, including the BIA's
Lozada requirements. The ineffective assistance claim must first
be presented to the BIA. Second, the dissent would eliminate the
first prong of the BIA's judicially approved ineffective
assistance standard requiring a showing of deficient performance.
Third, the dissent alters the standard of judicial review from
whether the BIA had substantial evidence on which to find deficient
performance and instead would substitute a new standard of review
in the guise of de novo review of fundamental fairness concerns.
Nothing in Congress's choice to use the word "the" in any way
negates or weakens the other explicit requirements in the statutory
bar to such collateral attacks.
The dissent's interpretation of § 1326(d) would also
multiply litigation and stress the already burdened federal
immigration agencies. The dissent's rule would create a
requirement that the government advance every conceivable basis
for removal in the original NTA and litigate each basis in an
immigration hearing, even where one ground for removal would
suffice. Cf. Magasouba, 543 F.3d at 16. If not, as is the case
for Castillo-Martinez, the government would have to re-notice and
redo the original immigration hearing, even though no party
disputes that Castillo-Martinez would likely be subject to
mandatory removal again.