United States of America v. Jesus Leonardo Castillo-Martinez

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

against him.

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).

We affirm.

I.

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

assistance.

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

proceeding).

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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II.

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.

A.

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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B.

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.

§ 1326(d).4

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

unfair.

1.

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

circumstances'").

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.

2.

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

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(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 "[1] a

deficient performance by counsel and [2] '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.

i.

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. §

1101(a)(43)(U).

- 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 -

ii.

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.

iii.

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.

3.

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

party's concessions.").

- 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

entirely.

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

aggravated felony.

- 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.

Affirmed.