Pinilla Perez v. Bondi - Noncitizen Removal Proceedings Deadline

23-6363- ag (L) Pinilla Perez v. Bondi Unite d States Court o f Appeals For the Sec ond Circ uit August Term, 2025 (Argued: Oc tober 21, 2025 Decided: February 5, 2026) Docket N o s. 23-6363- ag (L), 24-3151- ag (C ON) __________________ ______________ _____ LEONEL PINILLA PEREZ, Petitioner, v. PAMELA BOND I, UNITED STATES A TTORNEY GENERAL, Respondent. __________________ ______________ _____ Before: WESLEY, LOHIER, a nd MERRIA M, Circuit Judges. Noncitizens who rec eive a final order of removal from the Board of Immigration Appea ls (“BIA”) h ave 90 da ys to file a motion t o reope n their removal proceedings. The 90-day dead line for filing t he motion may be equit abl y to lled if extraordinary c ircumstance s prevented tim ely filing and the party seeki ng tolling acted wit h reasonable diligen ce throughout the tolli ng period. The question presented on appeal is what consti tutes “reasonable diligen ce” when a petitioner, ha ving been removed from t he United Sta tes, files a motion to reopen based on a chan ge in la w that arguab ly en tit les h im to r e lief from removal. H ere, the BIA denied petitioner Leo nel Pinilla Perez’s untimely motion to reopen his removal pr oceedings after concl uding that he h ad failed to act with reasonab le diligence. Beca use we conclude that the B IA provided

2 insufficient reason s for its dec ision, we GRANT Pin illa ’s pe tit ion chal leng ing the BIA’s order deny ing his motion to re open, No. 23-636 3, and we REM AND for further con sideration consi stent with this opinion. We therefore DISMISS as moot Pin illa’s pe tit ion f or r eview cha llen gin g the BIA’ s d enia l o f his mot ion to reconsider the orig inal order, No. 24 -3151. S COTT F O LETTA, J ILL A PPLEGATE, Neighborhood Defender Servic e of Harlem, New York, NY, for Petitioner. M ATTHEW B. G EORGE, Office of Imm igration Litiga tion (Brian Boynton, Principal Deputy Assistant Attor ney Gener al, C ivi l Div isi on; Anthon y P. Nicastr o, Assistant Director, Office of I mmigration Li tigation; Sheri R. Glaser, Senior Li tigation Counse l, Office o f Immigration Litiga tion, on the br ief), Un ited S tates Department of Justice, Washington, D C, for Respondent. P ER C URIAM: N oncit izen s who rec eive a final order of removal from the Board of Immigration Appea ls (“BIA”) h ave 90 da ys to file a motion t o reope n their removal proceedings. 8 U.S.C. § 12 29a(c)(7)(C)(i). Th e 90- day de adline for filing the motion “ ma y be eq uitabl y to lled if the party seeking tolli ng was prevented from timely filing in some extraor dinary way and passes with reas onable diligence through t he pe riod it seeks to h ave tolled.” Garcia P inach v. Bo ndi, 147 F.4th 117, 135 (2d C ir. 2025) (c leaned up). The question presented on appeal is what constitutes “reasonable diligence” when a peti tioner, having been removed

3 from the United S tates, files a mot ion to re open based on a cha nge in law that arguably e ntitles him to relief from remov al. In this case, the B IA de nie d p et ition er L eo nel P in i lla Perez ’s motion to reopen his rem oval proceedings after concluding that h e had failed to act with reasonable diligen ce in pursu it of his claim and was therefore not enti tle d to equit able t olli ng of th e 90-day filin g dea d line. Bec ause we con clude that the BIA provided insuff icient reas o ns for its decision, we GRANT P in illa’s pe tit ion challe ngin g th e B IA’ s order de nying his motion to reopen, N o. 23-6363, and we REMAND for fur ther consider ation consi stent with this op inion. We therefore DISMISS as moo t the p etit ion for review cha llen ging the BIA’ s d enial of his motion to reconsider th e orig inal order, No. 24-3151. I Pinilla, a Pana manian nation al, became a lawfu l permanent re sident in the United S tates in 1990 but soon af terward r an into troub le with the law. In 1993 he pleaded guilty to attempted sale of cocaine in violation of N ew York Sta te law. See N.Y. Pe n al Law § 220.39(1). Be tween 2000 and 2009 Pinil la also pleaded guilty to multiple charge s of fifth- degree possess ion of marijuan a, a Class B misdemeanor un der New York State law. See N.Y. Penal Law § 221.10 (2018).

4 Those same convic tions later prompted the federal Governm ent to in itia te removal proceedings against hi m in Nove mber 2009. In 2011 Pin illa, who had largel y represented hims elf during his removal p roceedings, was removed to Panama. While in Panama, Pin illa received a part ial reprieve when, in August 2019, the s tate legis lat ure in N ew York revised the state laws related to the possession of marijuana and rep ealed the prov ision c riminalizing fifth-de gree marijuana possession. See N.Y. C rim. Proc. § 160.50(3)(k) (i i). In March 2021 the sta te legis latur e author ized the j udic ial vacatur of all convictions, in clu ding Pin illa ’s, for fifth- degree marijuana posse ssion. See id. § 440. 10(1)(k). P inil la c laims tha t he first discovered the c hange in New York l aw in March 202 1 when, by chance, he spoke with a lawyer with whom he had b riefly worked in 2010. He further claims th at, with cou nsel, he quick ly f ile d a motion to reopen his re mova l proceedings and late r supplemented the adminis tra tive record wit h the for mal judicial vacaturs of h is ma riju an a convictions. 1 Pinil la made t wo arg uments to the B IA in suppor t of his motio n to reopen. First, he argued tha t the vacat ur of his pri or state conv ictions for marijuana 1 Due to what we co ncl ude is a s criv ener ’s error, t he vacatur s of P inilla’s conv ictions refer to N.Y. C rim. Proc. § 440.10(1)(h) rather t han § 440.10(1)(k).

5 offenses rende red those convictions an improper bas is for removab ility. Second, he maintained that intervening Suprem e Court and Second Circuit case law had invalidated his 1993 conviction for attempted sale of cocaine a s a categorical ly removable offense under federal l aw. In advancing both arguments P inilla fully acknowledged that h is motion to reopen was unt imely an d numbe r - barred under 8 U.S.C. § 1229a(c)(7) b ut ins isted th at his personal c ircumstances and the intervening changes in law entitled him to e quitab le toll ing. T he BIA de nied Pin il la ’s motion to r eopen b y order dated Mar ch 31, 2023. “A fter considering the circumstances,” it foun d that P ini lla wa s no t entitled to equitabl e tolling because he “ha [d] not exercis ed the requisite due d iligence in seeking reo pening.” No. 23-6363, S pec. App’x 4. And in an y eve nt, the a gency explained, Pin illa ’s 1 993 conviction for at tempted sa le of cocaine r emain ed a categ orica lly removable offense notwithst anding intervening Second Circuit law suggesting the co ntrary. A few months af ter the BIA’s den ial of Pi nilla’s motion, th is C ourt concluded in United States v. M inter, 80 F. 4th 406 (2d Cir. 20 23), that “Ne w York’s definition of cocaine is categorica lly broad er than the federal definition” of cocaine in the Controlled Substances Act. Id. at 411. Cit ing Minter, P inilla filed a

6 motion to reconsider, which the BIA als o denied by order date d November 6, 2024. Altho ugh the agency’s March 2 023 order had suggested o therwise, the November 2024 or der reasoned th at it ha d long been true that a cocaine conviction under Ne w York law did n ot c ategorica lly qualify as a removable offense under appl icable federal law. For that r eason, the agen cy concluded, Pinil la could an d should ha ve raised h is argument sooner than he did in orde r to meet the standard of reasonable di ligence. Pinil la then p e titio ne d this C our t to review both the BIA’s den ial of his motion to reopen and its denial of his motion to r econsider. We consolidated the two petitions and n ow turn t o the merits. 2 II T he Government concede s that P in illa’s 1993 conv iction for att empted sa le of cocaine would n o longer prov ide a ground for r emoval if h is removal proceedin gs were reopened. See Oral Ar gument Aud io Recor ding at 19:59 – 2 W e 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 Jura s v. Garlan d, 21 F.4th 53, 61 (2d Cir. 2021) (applying statut ory jurisdictional bar to appeal from de nial of m otion to re open). The B IA’s dec ision to d eny Pinilla ’s re quest fo r equitabl e toll ing is a que stion o f law for p urpose s of sectio n 1252(a)(2)(D). See Guerrero - Laspr illa v. Barr, 589 U.S. 221, 227 (2020). We therefore have jurisdiction to review it.

7 20:09. 3 As the BIA di d, we assume w ithout deciding that the same holds true of Pinil la’s convictions f or possession of mari juana. If so, t hen P in illa has no convictions that re main valid for purpose s of establishing h is r emovability. The central quest ion for us, then, is whether the BIA improperly denied Pinilla ’s request for equi table tolli ng to permit him to move to reopen his r emoval proceedings. A As noted above, a par ty has 90 days after the BIA en ters a final or der of removal to file a mo tion to reopen the removal proce edings. 8 U.S.C. § 1229a(c)(7)(C)(i). T he BIA may thereafter consider the part y’s motion o nly if he is enti tled to e quitab le tol ling of the f iling deadlin e. See Garcia Pinach, 14 7 F.4th at 135. A pet itio ner seeking equitable tol ling bears the burden of esta blishing two element s: (1) that an “extraordinary” circumstan ce “prevente d [him] fro m timel y filing,” and (2) that he “ passe [d] with reasonable diligenc e through the period 3 In view of the Gove rnme nt’s con cession, we need n ot consi der Pini lla’s argu ment that the BIA erred in deny ing Pinilla discretionary r elief from removal under for mer section 212(c) of the Immigrati on and Na tionality A ct, 8 U.S.C. § 1182(c) (repealed 1996). That provisi on autho rizes t he Attorn ey Genera l to gra nt reli ef from rem oval to n oncitiz ens who pl eaded gu ilty to c ertain remova ble of fens es prior to 19 97, see I.N.S. v. St. Cyr, 533 U.S. 289, 293, 326 (2001), but Pinilla would no t ne ed this relief if his 1993 conviction is not a r emovable offense.

8 [he] seeks to have t olled.” Id. (cleaned up); see Clark v. Ha nley, 89 F.4th 78, 92 (2d Cir. 2023); Doe v. U nited States, 76 F.4th 64, 71 (2d C ir. 2023). In considering Pin illa’s motion, the BIA d id not resolve wheth er a change in law can satisf y the “extraordinary c ircumstance” e lement of equ itable tolling. Inste ad, t he agency f ound that P inill a fail ed to establish th e second elemen t for tollin g —in other words, that he “ha[d] not exercised the requi site due diligen ce” in pur suin g h is righ t s. No. 23-636 3, Spec. App’x 3. “[W] e review the BIA ’s decision not to grant equit able tolling for abuse of discreti on, asking whether there is a reasonable bas is for its ” decis ion. Garcia Pinach, 147 F.4th at 1 35 (quotation marks omitted). Because a “denial of immigration relief stands or fal ls on the reas ons given by the I [mmigration] J [udge] or BIA,” Castellanos-Ve ntura v. Gar land, 118 F.4th 250, 254 (2d Cir. 2 024) (quotation marks o mitted), we address only whether the BIA a bused its discr etion when it denied Pinilla’s r equest for eq uitable tolling b ased on a lack of dilige nce. We do not address w hether a c hange in law can qua lify a s an extraordinary c ircumstance for purposes o f tolling.

9 B T he party seek ing t ol ling must “pas s with reasonable diligence th r ough the period it seeks t o have tol led.” Garcia Pinach, 147 F.4t h at 135 (cleaned up). In dete rm inin g the “ period ” through wh ich Pin illa must demon strate th at he exercised di ligence, we turn to our dec ision in Rashid v. Mukasey, 533 F.3d 127 (2d Cir. 2008). There we held th at “ in order to e quitably toll the fi ling deadl ine for a motion to reopen based on ineffe ctive assi stance of counse l, an alien mus t demonst rate that he or she has exerci sed due diligen ce during the entire period he or she seeks t o toll.” Id. at 132. “ Th is in clu des both the period of time before the ineffective ass istance of counsel was or sh ould have been d iscovered and the period from that poi nt until the m otion to reop en is filed.” Id. T he requirement that the pe tition er ac t dilige n tl y durin g “the entire period he seeks to toll,” id. (emphasis added), als o applies outside th e context of ineffective assistance claims. W e apply i t, for example, to assess wh ether a motion t o reopen meri ts equitable tolling bas ed on the d iscovery of n ew medical eviden ce, see Garcia Pinach, 147 F.4th at 1 35–36, and we app ly it today t o Pin illa ’s motion to reope n based on an inter vening chan ge in law. We recognize that R ashid co uld b e read to require a petit ione r to

10 demonstr ate that he t ook steps to fi le a motion to r eopen before any change in law took place (th at is, be fore he be came entitled to reli ef). Bu t no one ser iously argue s that Rashid go es that far. Nor does equity permit such a requirement. “[E]qui table tolling asks whethe r a petitioner has been pursu ing his rights dilige nt ly.” Williams v. Garland, 59 F. 4th 620, 641 (4th C ir. 2023) (quoting Holla nd v. Florida, 560 U.S. 631, 649 (20 10)). But p et ition ers whose claims for reli ef are barred by law “ha [ve ] no ‘righ ts’ to pursu e” until the law chan ges to entitle them to relief. Id. Beca use a petition er cann ot reasonab ly be expecte d to act on a change in law that has ye t to happen, we hold that the reasonable diligence standard does no t oblige a petitio ner who has be en removed fr om the United States to take ste ps to file a mo tion to reop en based on an in tervening change in law before th e change takes place. C Famil iar p rinc iple s o f e quity a lso inform our analysis of the d ilige nce required of Pini lla after New Yor k amende d its marijuana laws. “ As the Supreme Court [has] rem inded, the co re purpose of equita ble tolling is to escape the ‘ evils of archaic rigidity’ a nd ‘to accord al l the relief neces sary to correct .. . particular injus tices. ’” Lugo -Re sendez v. Lynch, 831 F.3d 337, 345 (5th Cir. 2016) (e llipsis in

11 origin al) (quo tin g Holland, 560 U.S. at 650). “T he diligence requi red for equitabl e tolling purposes is ” therefore “reaso nable diligence, not maxim um feasible dilige nce.” Doe, 76 F.4th at 73 (quot ing Ho lland, 560 U.S. at 653). To determi ne whether equi table tolling is a ppropriate, t he BIA should avoi d applying a “per se” tempo ral rule, Wang v. Bd. of Immi gr. Appeals, 5 08 F.3d 710, 715 (2d Cir. 2007), and must ins tead consider whether the petitioner “ act[ed] as dil igen tly a s reasonably could have been expected ” to file h is mo tio n under the tota lity of the circumstances, Baldayaque v. United States, 338 F.3d 145, 153 (2d Cir. 2003); see Williams, 59 F.4th at 641–43. In determi ning whether a motion to reopen meri ts equitable tolli ng based on a favorable chang e in law, “we f ocus on the reasonable expe ctations of someone in the pet itioner ’s position” who has been r emoved and now l ives abroad. Bracey v. Su perintendent Ro ckview SCI, 986 F.3d 274, 28 6 (3d Cir. 2021) (emphasis added) (cleaned up). W e accor dingly do not expect th e petitioner “[to] continuously m onitor publ ic sources for year s on the unlike ly chance that he might learn somet hing which would be us eful to his case.” I d. (cleaned up). Nor do we “ask, in a vacuum,” “whether [the peti tioner] should have contacted X number of attorne ys” during the period after his removal, h oping to disc over

12 that the law has chan ged in his favor, or pressed X number of f amil y members in the Uni ted States to “ stay abreast of immigration law.” Willia ms, 59 F.4th a t 641– 42. These steps of “‘ extreme dil igence’ or ‘exceptio nal diligence’” are sufficient but not necessary to toll the 90-da y filing deadline. See B aldayaque, 338 F.3d at 153. A removed petition er’s fail ure to ta ke the m does no t negate reasonable dilige nce. When a p etitioner “has [n o] reasonab le basis to exp ect that investigation woul d uncover r elevant infor mation,” then “ his decision n ot to investigate is not a failure to exerci se due diligen ce.” Bracey, 9 86 F.3d at 286 (cleaned up). As the Fifth Circ uit obse rved, “t he reality ” is that m any depar ted noncitizens “are poor, uneducated, uns kil led in the Eng lish lan guag e, an d effectively unable to follow deve lopments in the A merican leg al syste m.” Lugo - Resendez, 831 F.3d at 345. In und erta king i ts di ligenc e in qu iry, t he BIA sh ould give due consideration to, among other t hings, whether the noncitizen (1) had the means and capac ity to learn of, an d act upon, the change in law (for examp le, the noncitizen’s re moval abroa d, detention, poverty, lang uage barr iers, and lack

13 of access to legal info rmation 4); (2) took reasonable ste ps to inves tigate and pursue rel ief (for example, reconnec ting with prior counsel or seeking new counsel); and (3) ac ted reason ably swiftly to fi le his motion to r eopen after discovering the material change in law. See William s, 59 F.4th a t 643; see also Goulart v. Garland, 18 F.4th 653, 663 (9th Cir. 2021) (Korman, J., dissentin g). P rinci ples of eq uit y e s pecia lly co unsel in f avor of tolling whe n “ it is e vide n t tha t the basis [for the p etitioner’s remo val may] now [be] in valid.” Lugo -Resendez, 831 F.3d at 345. III With these principles in mind, we con clude t hat the BIA ab used its discr etion in f inding that Pinil la failed to demonstra te due diligence in pursui ng his mo tion to r e open. In i ts de cis ion, the BIA e xpla ine d on ly th at P in i lla was no t entitled to tolling b ecause he wai ted “app roximately 2 year s” after New York revised its mar ijuana law s to file his motion. No. 23-6 363, Spe c. App’x 4. Th e 4 In Watson v. U nited States, 865 F.3d 123 (2d Cir. 2017), we suggested that a litigant’s “lac k of educ ation, pro se sta tus, or ign orance of the righ t to brin g a cl aim” are n ot, withou t more, “ex traor dinary c ircums tances ” that satis fy the f irst req uiremen t of equitable tolling. Id. at 132– 33. But the se biograp hical facts are not irrele vant to the diligence inquiry, which r equires a court to consider whether a petitioner “a cted as diligently as re asonably could have been ex pected under the circumstances.” Doe, 76 F.4th at 7 3 (quotati on marks omi tted).

14 agency’s stated jus tification is not the “ mi nim um leve l of ana lys is ” tha t we require “ if judic ial r evie w is t o be mean ing ful.” Garcia Pinach, 147 F.4t h at 136 (quotation marks o mitted). “[T]he test for equitable toll ing, both gener ally and in the immigration context, is n ot the length of the delay in f iling the [mo tion]; it is wheth er the claimant could reason ably have been expected to have file d earlier. ” Pervaiz v. Gonzales, 405 F.3d 488, 490 (7th C ir. 2005). It is u nc lear t o us what te st the B IA ap plie d or whether it considered Pinilla ’s a ctio ns an d circumstances predating his motio n. And b ecause it provided “only sum mary or conclusory state ments” in suppor t of its decision, the BIA ab us ed its dis cret ion. See Poradisova v. Gonz ales, 420 F.3d 70, 77 (2d C ir. 2005) (quotati on marks omitted). On reman d, the BIA s hou ld co nside r Pin illa ’s motio n in a manner that is consistent with this opinion. 5 5 Because w e remand on this basis, we need not address wh ether the BIA erred when it denied Pinilla’s motio n to reopen his remo val proceedings su a sponte.

15 IV For the foreg oing reasons, we GRANT Pin illa’ s pet it ion for re view w ith respect to the BIA’s order denyi ng his motion to reop en, and th e case is REMA ND ED for further consideration co nsistent with this opinion. We DISMISS as moo t Pinilla’s pet ition with re spect to the BIA’s or der in No. 24- 3151 denying h is motion for recons ideration.