Pinilla Perez v. Bondi

• Court: Court of Appeals for the Second Circuit
• Decided: February 5, 2026
• Docket: 23-6363
• Status: Published

Opinion

23-6363-ag (L) Pinilla Perez v. Bondi

United States Court of Appeals For the Second Circuit August Term, 2025

(Argued: October 21, 2025 Decided: February 5, 2026)

Docket Nos. 23-6363-ag (L), 24-3151-ag (CON) _____________________________________

LEONEL PINILLA PEREZ,

Petitioner,

v.

PAMELA BONDI, UNITED STATES ATTORNEY GENERAL,

Respondent. _____________________________________ Before:

WESLEY, LOHIER, and MERRIAM, Circuit Judges.

Noncitizens who receive a final order of removal from the Board of Immigration Appeals (“BIA”) have 90 days to file a motion to reopen their removal proceedings. The 90-day deadline for filing the motion may be equitably tolled if extraordinary circumstances prevented timely filing and the party seeking tolling acted with reasonable diligence throughout the tolling period. The question presented on appeal is what constitutes “reasonable diligence” when a petitioner, having been removed from the United States, files a motion to reopen based on a change in law that arguably entitles him to relief from removal. Here, the BIA denied petitioner Leonel Pinilla Perez’s untimely motion to reopen his removal proceedings after concluding that he had failed to act with reasonable diligence. Because we conclude that the BIA provided insufficient reasons for its decision, we GRANT Pinilla’s petition challenging the BIA’s order denying his motion to reopen, No. 23-6363, and we REMAND for further consideration consistent with this opinion. We therefore DISMISS as moot Pinilla’s petition for review challenging the BIA’s denial of his motion to reconsider the original order, No. 24-3151.

SCOTT FOLETTA, JILL APPLEGATE, Neighborhood Defender Service of Harlem, New York, NY, for Petitioner.

MATTHEW B. GEORGE, Office of Immigration Litigation (Brian Boynton, Principal Deputy Assistant Attorney General, Civil Division; Anthony P. Nicastro, Assistant Director, Office of Immigration Litigation; Sheri R. Glaser, Senior Litigation Counsel, Office of Immigration Litigation, on the brief), United States Department of Justice, Washington, DC, for Respondent.

PER CURIAM:

Noncitizens who receive a final order of removal from the Board of

Immigration Appeals (“BIA”) have 90 days to file a motion to reopen their

removal proceedings. 8 U.S.C. § 1229a(c)(7)(C)(i). The 90-day deadline for filing

the motion “may be equitably tolled if the party seeking tolling was prevented

from timely filing in some extraordinary way and passes with reasonable

diligence through the period it seeks to have tolled.” Garcia Pinach v. Bondi, 147

F.4th 117, 135 (2d Cir. 2025) (cleaned up). The question presented on appeal is

what constitutes “reasonable diligence” when a petitioner, having been removed

2 from the United States, files a motion to reopen based on a change in law that

arguably entitles him to relief from removal.

In this case, the BIA denied petitioner Leonel Pinilla Perez’s motion to

reopen his removal proceedings after concluding that he had failed to act with

reasonable diligence in pursuit of his claim and was therefore not entitled to

equitable tolling of the 90-day filing deadline. Because we conclude that the BIA

provided insufficient reasons for its decision, we GRANT Pinilla’s petition

challenging the BIA’s order denying his motion to reopen, No. 23-6363, and we

REMAND for further consideration consistent with this opinion. We therefore

DISMISS as moot the petition for review challenging the BIA’s denial of his

motion to reconsider the original order, No. 24-3151.

I

Pinilla, a Panamanian national, became a lawful permanent resident in the

United States in 1990 but soon afterward ran into trouble with the law. In 1993

he pleaded guilty to attempted sale of cocaine in violation of New York State

law. See N.Y. Penal Law § 220.39(1). Between 2000 and 2009 Pinilla also pleaded

guilty to multiple charges of fifth-degree possession of marijuana, a Class B

misdemeanor under New York State law. See N.Y. Penal Law § 221.10 (2018).

3 Those same convictions later prompted the federal Government to initiate

removal proceedings against him in November 2009. In 2011 Pinilla, who had

largely represented himself during his removal proceedings, was removed to

Panama.

While in Panama, Pinilla received a partial reprieve when, in August 2019,

the state legislature in New York revised the state laws related to the possession

of marijuana and repealed the provision criminalizing fifth-degree marijuana

possession. See N.Y. Crim. Proc. § 160.50(3)(k)(ii). In March 2021 the state

legislature authorized the judicial vacatur of all convictions, including Pinilla’s,

for fifth-degree marijuana possession. See id. § 440.10(1)(k). Pinilla claims that he

first discovered the change in New York law in March 2021 when, by chance, he

spoke with a lawyer with whom he had briefly worked in 2010. He further

claims that, with counsel, he quickly filed a motion to reopen his removal

proceedings and later supplemented the administrative record with the formal

judicial vacaturs of his marijuana convictions. 1

Pinilla made two arguments to the BIA in support of his motion to reopen.

First, he argued that the vacatur of his prior state convictions for marijuana

1 Due to what we conclude is a scrivener’s error, the vacaturs of Pinilla’s convictions refer to N.Y. Crim. Proc. § 440.10(1)(h) rather than § 440.10(1)(k). 4 offenses rendered those convictions an improper basis for removability. Second,

he maintained that intervening Supreme Court and Second Circuit case law had

invalidated his 1993 conviction for attempted sale of cocaine as a categorically

removable offense under federal law. In advancing both arguments Pinilla fully

acknowledged that his motion to reopen was untimely and number-barred

under 8 U.S.C. § 1229a(c)(7) but insisted that his personal circumstances and the

intervening changes in law entitled him to equitable tolling.

The BIA denied Pinilla’s motion to reopen by order dated March 31, 2023.

“After considering the circumstances,” it found that Pinilla was not entitled to

equitable tolling because he “ha[d] not exercised the requisite due diligence in

seeking reopening.” No. 23-6363, Spec. App’x 4. And in any event, the agency

explained, Pinilla’s 1993 conviction for attempted sale of cocaine remained a

categorically removable offense notwithstanding intervening Second Circuit law

suggesting the contrary.

A few months after the BIA’s denial of Pinilla’s motion, this Court

concluded in United States v. Minter, 80 F.4th 406 (2d Cir. 2023), that “New York’s

definition of cocaine is categorically broader than the federal definition” of

cocaine in the Controlled Substances Act. Id. at 411. Citing Minter, Pinilla filed a

5 motion to reconsider, which the BIA also denied by order dated November 6,

2024. Although the agency’s March 2023 order had suggested otherwise, the

November 2024 order reasoned that it had long been true that a cocaine

conviction under New York law did not categorically qualify as a removable

offense under applicable federal law. For that reason, the agency concluded,

Pinilla could and should have raised his argument sooner than he did in order to

meet the standard of reasonable diligence.

Pinilla then petitioned this Court to review both the BIA’s denial of his

motion to reopen and its denial of his motion to reconsider. We consolidated the

two petitions and now turn to the merits. 2

II

The Government concedes that Pinilla’s 1993 conviction for attempted sale

of cocaine would no longer provide a ground for removal if his removal

proceedings were reopened. See Oral Argument Audio Recording at 19:59–

2 We have jurisdiction to review the BIA’s denial of a motion to reopen only for “constitutional claims” and “questions of law.” 8 U.S.C. § 1252(a)(2)(C), (D); see Juras v. Garland, 21 F.4th 53, 61 (2d Cir. 2021) (applying statutory jurisdictional bar to appeal from denial of motion to reopen). The BIA’s decision to deny Pinilla’s request for equitable tolling is a question of law for purposes of section 1252(a)(2)(D). See Guerrero- Lasprilla v. Barr, 589 U.S. 221, 227 (2020). We therefore have jurisdiction to review it.

6 20:09. 3 As the BIA did, we assume without deciding that the same holds true of

Pinilla’s convictions for possession of marijuana. If so, then Pinilla has no

convictions that remain valid for purposes of establishing his removability. The

central question for us, then, is whether the BIA improperly denied Pinilla’s

request for equitable tolling to permit him to move to reopen his removal

proceedings.

A

As noted above, a party has 90 days after the BIA enters a final order of

removal to file a motion to reopen the removal proceedings. 8 U.S.C.

§ 1229a(c)(7)(C)(i). The BIA may thereafter consider the party’s motion only if he

is entitled to equitable tolling of the filing deadline. See Garcia Pinach, 147 F.4th at

135. A petitioner seeking equitable tolling bears the burden of establishing two

elements: (1) that an “extraordinary” circumstance “prevented [him] from timely

filing,” and (2) that he “passe[d] with reasonable diligence through the period

3In view of the Government’s concession, we need not consider Pinilla’s argument that the BIA erred in denying Pinilla discretionary relief from removal under former section 212(c) of the Immigration and Nationality Act, 8 U.S.C. § 1182(c) (repealed 1996). That provision authorizes the Attorney General to grant relief from removal to noncitizens who pleaded guilty to certain removable offenses prior to 1997, see I.N.S. v. St. Cyr, 533 U.S. 289, 293, 326 (2001), but Pinilla would not need this relief if his 1993 conviction is not a removable offense. 7 [he] seeks to have tolled.” Id. (cleaned up); see Clark v. Hanley, 89 F.4th 78, 92 (2d

Cir. 2023); Doe v. United States, 76 F.4th 64, 71 (2d Cir. 2023).

In considering Pinilla’s motion, the BIA did not resolve whether a change

in law can satisfy the “extraordinary circumstance” element of equitable tolling.

Instead, the agency found that Pinilla failed to establish the second element for

tolling—in other words, that he “ha[d] not exercised the requisite due diligence”

in pursuing his rights. No. 23-6363, Spec. App’x 3.

“[W]e review the BIA’s decision not to grant equitable tolling for abuse of

discretion, asking whether there is a reasonable basis for its” decision. Garcia

Pinach, 147 F.4th at 135 (quotation marks omitted). Because a “denial of

immigration relief stands or falls on the reasons given by the I[mmigration]

J[udge] or BIA,” Castellanos-Ventura v. Garland, 118 F.4th 250, 254 (2d Cir. 2024)

(quotation marks omitted), we address only whether the BIA abused its

discretion when it denied Pinilla’s request for equitable tolling based on a lack of

diligence. We do not address whether a change in law can qualify as an

extraordinary circumstance for purposes of tolling.

8 B

The party seeking tolling must “pass with reasonable diligence through

the period it seeks to have tolled.” Garcia Pinach, 147 F.4th at 135 (cleaned up).

In determining the “period” through which Pinilla must demonstrate that he

exercised diligence, we turn to our decision in Rashid v. Mukasey, 533 F.3d 127 (2d

Cir. 2008). There we held that “in order to equitably toll the filing deadline for a

motion to reopen based on ineffective assistance of counsel, an alien must

demonstrate that he or she has exercised due diligence during the entire period

he or she seeks to toll.” Id. at 132. “This includes both the period of time before

the ineffective assistance of counsel was or should have been discovered and the

period from that point until the motion to reopen is filed.” Id. The requirement

that the petitioner act diligently during “the entire period he seeks to toll,” id.

(emphasis added), also applies outside the context of ineffective assistance

claims. We apply it, for example, to assess whether a motion to reopen merits

equitable tolling based on the discovery of new medical evidence, see Garcia

Pinach, 147 F.4th at 135–36, and we apply it today to Pinilla’s motion to reopen

based on an intervening change in law.

We recognize that Rashid could be read to require a petitioner to

9 demonstrate that he took steps to file a motion to reopen before any change in law

took place (that is, before he became entitled to relief). But no one seriously

argues that Rashid goes that far. Nor does equity permit such a requirement.

“[E]quitable tolling asks whether a petitioner has been pursuing his rights

diligently.” Williams v. Garland, 59 F.4th 620, 641 (4th Cir. 2023) (quoting Holland

v. Florida, 560 U.S. 631, 649 (2010)). But petitioners whose claims for relief are

barred by law “ha[ve] no ‘rights’ to pursue” until the law changes to entitle them

to relief. Id. Because a petitioner cannot reasonably be expected to act on a

change in law that has yet to happen, we hold that the reasonable diligence

standard does not oblige a petitioner who has been removed from the United

States to take steps to file a motion to reopen based on an intervening change in

law before the change takes place.

C

Familiar principles of equity also inform our analysis of the diligence

required of Pinilla after New York amended its marijuana laws. “As the Supreme

Court [has] reminded, the core purpose of equitable tolling is to escape the ‘evils

of archaic rigidity’ and ‘to accord all the relief necessary to correct . . . particular

injustices.’” Lugo-Resendez v. Lynch, 831 F.3d 337, 345 (5th Cir. 2016) (ellipsis in

10 original) (quoting Holland, 560 U.S. at 650). “The diligence required for equitable

tolling purposes is” therefore “reasonable diligence, not maximum feasible

diligence.” Doe, 76 F.4th at 73 (quoting Holland, 560 U.S. at 653). To determine

whether equitable tolling is appropriate, the BIA should avoid applying a “per

se” temporal rule, Wang v. Bd. of Immigr. Appeals, 508 F.3d 710, 715 (2d Cir. 2007),

and must instead consider whether the petitioner “act[ed] as diligently as

reasonably could have been expected” to file his motion under the totality of the

circumstances, Baldayaque v. United States, 338 F.3d 145, 153 (2d Cir. 2003); see

Williams, 59 F.4th at 641–43.

In determining whether a motion to reopen merits equitable tolling based

on a favorable change in law, “we focus on the reasonable expectations of

someone in the petitioner’s position” who has been removed and now lives

abroad. Bracey v. Superintendent Rockview SCI, 986 F.3d 274, 286 (3d Cir. 2021)

(emphasis added) (cleaned up). We accordingly do not expect the petitioner

“[to] continuously monitor public sources for years on the unlikely chance that

he might learn something which would be useful to his case.” Id. (cleaned up).

Nor do we “ask, in a vacuum,” “whether [the petitioner] should have contacted

X number of attorneys” during the period after his removal, hoping to discover

11 that the law has changed in his favor, or pressed X number of family members in

the United States to “stay abreast of immigration law.” Williams, 59 F.4th at 641–

42. These steps of “‘extreme diligence’ or ‘exceptional diligence’” are sufficient

but not necessary to toll the 90-day filing deadline. See Baldayaque, 338 F.3d at

153. A removed petitioner’s failure to take them does not negate reasonable

diligence. When a petitioner “has [no] reasonable basis to expect that

investigation would uncover relevant information,” then “his decision not to

investigate is not a failure to exercise due diligence.” Bracey, 986 F.3d at 286

(cleaned up).

As the Fifth Circuit observed, “the reality” is that many departed

noncitizens “are poor, uneducated, unskilled in the English language, and

effectively unable to follow developments in the American legal system.” Lugo-

Resendez, 831 F.3d at 345. In undertaking its diligence inquiry, the BIA should

give due consideration to, among other things, whether the noncitizen (1) had

the means and capacity to learn of, and act upon, the change in law (for example,

the noncitizen’s removal abroad, detention, poverty, language barriers, and lack

12 of access to legal information 4); (2) took reasonable steps to investigate and

pursue relief (for example, reconnecting with prior counsel or seeking new

counsel); and (3) acted reasonably swiftly to file his motion to reopen after

discovering the material change in law. See Williams, 59 F.4th at 643; see also

Goulart v. Garland, 18 F.4th 653, 663 (9th Cir. 2021) (Korman, J., dissenting).

Principles of equity especially counsel in favor of tolling when “it is evident that

the basis [for the petitioner’s removal may] now [be] invalid.” Lugo-Resendez, 831

F.3d at 345.

III

With these principles in mind, we conclude that the BIA abused its

discretion in finding that Pinilla failed to demonstrate due diligence in pursuing

his motion to reopen. In its decision, the BIA explained only that Pinilla was not

entitled to tolling because he waited “approximately 2 years” after New York

revised its marijuana laws to file his motion. No. 23-6363, Spec. App’x 4. The

4In Watson v. United States, 865 F.3d 123 (2d Cir. 2017), we suggested that a litigant’s “lack of education, pro se status, or ignorance of the right to bring a claim” are not, without more, “extraordinary circumstances” that satisfy the first requirement of equitable tolling. Id. at 132–33. But these biographical facts are not irrelevant to the diligence inquiry, which requires a court to consider whether a petitioner “acted as diligently as reasonably could have been expected under the circumstances.” Doe, 76 F.4th at 73 (quotation marks omitted). 13 agency’s stated justification is not the “minimum level of analysis” that we

require “if judicial review is to be meaningful.” Garcia Pinach, 147 F.4th at 136

(quotation marks omitted). “[T]he test for equitable tolling, both generally and

in the immigration context, is not the length of the delay in filing the [motion]; it

is whether the claimant could reasonably have been expected to have filed

earlier.” Pervaiz v. Gonzales, 405 F.3d 488, 490 (7th Cir. 2005). It is unclear to us

what test the BIA applied or whether it considered Pinilla’s actions and

circumstances predating his motion. And because it provided “only summary or

conclusory statements” in support of its decision, the BIA abused its discretion.

See Poradisova v. Gonzales, 420 F.3d 70, 77 (2d Cir. 2005) (quotation marks

omitted). On remand, the BIA should consider Pinilla’s motion in a manner that

is consistent with this opinion. 5

5 Because we remand on this basis, we need not address whether the BIA erred when it denied Pinilla’s motion to reopen his removal proceedings sua sponte. 14 IV

For the foregoing reasons, we GRANT Pinilla’s petition for review with

respect to the BIA’s order denying his motion to reopen, and the case is

REMANDED for further consideration consistent with this opinion. We

DISMISS as moot Pinilla’s petition with respect to the BIA’s order in No. 24-

3151 denying his motion for reconsideration.