Olawole Oluwajana v. MERRICK B. GARLAND, Attorney General of the United States

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 21-1804
O LAWOLE O LUWAJANA,
Petitioner,
v.
M ERRICK B. GARLAND,
Attorney General of the United States,
Respondent.
____________________
Petition for Review of an Order
of the Board of Immigration Appeals.
No. A061-591-186
____________________
A RGUED DECEMBER 1, 2021 — DECIDED M ARCH 9, 2022
A MENDED M AY 3, 2022
____________________
Before M ANION , BRENNAN , and JACKSON -A KIWUMI , Circuit
Judges.
M ANION , Circuit Judge. After an immigration judge or-
dered him removed from the United States, Olawole Olu-
wajana appealed to the Board of Immigration Appeals and re-
tained counsel to represent him. But the government was

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2 No. 21-1804
slow in providing a copy of Oluwajana’s immigration file,
without which his attorney could not prepare a brief. The
Board granted one extension but denied a second, suggesting
that Oluwajana instead submit his brief with a motion seeking
leave to file it late. When he did so, less than two weeks after
the submission deadline, the Board denied the motion in a
cursory—and factually erroneous—footnote. And having re-
jected the brief, the Board upheld the removal order without
considering Oluwajana’s allegations of error by the immigra-
tion judge. Based on the undisputed circumstances of this
case, we conclude that the Board abused its discretion by un-
reasonably rejecting Oluwajana’s brief. We therefore grant the
petition for review, vacate the Board’s order, and remand for
further proceedings.
Originally from Nigeria, Oluwajana became a lawful per-
manent resident of the United States in 2011. In 2017, he was
convicted in Illinois state court of criminal sexual assault and
aggravated criminal sexual abuse. Based on these convictions,
the Department of Homeland Security charged him with re-
movability. See 8 U.S.C. § 1227(a)(2)(A)(iii) (“Any alien who is
convicted of an aggravated felony at any time after admission
is deportable.”).
He was unrepresented throughout immigration court pro-
ceedings. At the final hearing, the immigration judge (IJ)
wanted to know whether Oluwajana had been able to find an
attorney. When Oluwajana said he had not, the IJ asked
whether he was prepared to proceed anyway, and Oluwajana
said he was. After confirming the state crimes of which Olu-
wajana was convicted, the IJ inquired whether there was any
reason he could not return to Nigeria. Oluwajana stated that
his entire family resided in the United States and that he

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No. 21-1804 3
believed he would be targeted by criminals upon his return to
Nigeria. In response to the IJ, counsel for the government
stated that she did not believe Oluwajana had a basis to file
an “I-589,” an immigration form by which a person may re-
quest relief from an order of removal.
A few weeks after the hearing, Oluwajana was ordered re-
moved from the United States. The IJ concluded that the state
crimes of which Oluwajana was convicted constituted aggra-
vated felonies and that no apparent eligibility for relief from
removal had been demonstrated.
Oluwajana timely appealed to the Board in June 2020.
Three months later, he retained counsel. His attorney
promptly requested a copy of Oluwajana’s immigration file
from the Executive Office of Immigration Review (EOIR) and
asked the Board to delay setting a briefing schedule until he
received it. Eventually, the Board set a date of February 3,
2021, for any brief to be filed. As the initial due date neared,
Oluwajana’s counsel advised that he still had not received a
copy of the file, including transcripts of immigration court
proceedings. The Board extended the due date for the brief to
February 24. As the new date approached, the EOIR still had
not supplied the file, and Oluwajana’s counsel asked the
Board for another extension. While the extension request was
pending before the Board, counsel at last received the case file
on February 16. With only a week remaining before the Feb-
ruary 24 due date, counsel advised the Board that he could
not properly review the materials and prepare a brief in time;
he sought a 21-day extension.
The Board denied the second extension request. Instead, it
informed counsel that he could submit a brief after the due
date along with a motion for its consideration.

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4 No. 21-1804
Oluwajana’s counsel filed the brief and the accompanying
motion on March 8, 2021—12 days after the February 24 due
date. The brief alleged that the IJ violated Oluwajana’s due
process rights by failing to give him an opportunity to file a
Form I-589 and by not obtaining a knowing, intelligent, and
voluntary waiver of the right to counsel. The brief further al-
leged that neither of Oluwajana’s convictions constituted ag-
gravated felonies justifying his removal. The accompanying
motion asserted that counsel received a copy of the immigra-
tion case file from the EOIR so late that he did not have time
to review its contents, consult with his client, and submit a
brief by the February 24 deadline.
The Board issued its order in April 2021. First, it rejected
Oluwajana’s brief in a footnote, which read in its entirety:
The respondent filed two motions for extension
of time to file a brief. The first was granted on
January 26, 2021; the second was denied on Feb-
ruary 24, 2021. The respondent’s brief was due
on February 3, 2021. It was received on March 8,
2021. The respondent requests acceptance of the
late-filed brief. Because the respondent’s second
request for an extension of time was denied and
because the respondent’s brief is untimely by 33
days, the motion to accept the late-filed brief is
denied.
The Board then concluded that Oluwajana’s state convictions
rendered him removable and that he was therefore ineligible
for asylum or withholding of removal or other relief. The
Board dismissed Oluwajana’s appeal without directly ad-
dressing the arguments raised in his brief. This petition for
review followed.

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No. 21-1804 5
At the outset, we must ensure that we have jurisdiction to
hear this petition. Generally, the Immigration Code author-
izes our review of a final order of removal, 8 U.S.C.
§ 1252(a)(1), but not when removal is predicated on an alien
having committed an aggravated felony, id. § 1252(a)(2)(C).
Yet even in the latter case, we retain jurisdiction to consider
“questions of law.” Id. § 1252(a)(2)(D). Whether Oluwajana’s
prior convictions count as aggravated felonies, an issue he
raised both in this court and in the rejected brief he submitted
to the Board, is just such a question. Eke v. Mukasey, 512 F.3d
372, 378 (7th Cir. 2008). Because the Board’s final order of re-
moval, among other things, concluded that Oluwajana’s state
convictions constituted aggravated felonies, we are secure in
our jurisdiction to review that order, including the Board’s
preliminary decision to reject his brief arguing that the basis
for his removal was legally erroneous.
The parties agree that we should return this case to the
Board for further proceedings. But Oluwajana contends that
the Board abused its discretion in rejecting his late-filed brief
and requests a remand with instructions that the Board accept
it. The government, in contrast, urges a general remand to
give the Board the opportunity to reconsider whether to ac-
cept the brief and, this time, provide an adequate explanation
for its decision.
The rules surrounding the submission of a brief to the
Board reflect a resolve to keep administrative proceedings
moving expeditiously. Twenty-one days is the default period
for all parties to file initial briefs, and reply briefs may not be
filed as a matter of course. 8 C.F.R. § 1003.3(c)(1) (2020).* Upon
* Section 1003.3(c)(1) was amended in 2021, but that version is not ap-
plicable in Oluwajana’s case because he filed his Board appeal before the

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6 No. 21-1804
a showing of good cause, the Board may extend the deadline
to file an initial brief for no more than 90 days. Id. “It is also
the Board’s policy not to grant second briefing extension re-
quests” except in “rare circumstances.” EOIR, Board of Immi-
gration Appeals Practice Manual, Ch. 4.7(c)(i)(A) & (B) (updated
Jan. 8, 2021). But, as most relevant here, the rules provide that,
“[i]n its discretion, the Board may consider a brief that has
been filed out of time.” Id. Given that the issue is decided by
the Board on a discretionary basis, we unsurprisingly review
the denial of a motion to file a late brief for abuse of that dis-
cretion. Dakaj v. Holder, 580 F.3d 479, 481 (7th Cir. 2009).
Deferential though that standard is, however, the Board
must still exercise its discretion in a reasonable manner. To
that end, this court must “ensure that the Board’s legal inter-
pretations stay within the boundaries permitted to it and that
it has not unreasonably failed to consider relevant factual in-
formation” presented in the record before it. Chowdhury v.
Ashcroft, 241 F.3d 848, 852 (7th Cir. 2001).
The Board provided only two reasons for denying Olu-
wajana’s motion to submit a brief out of time: (1) the second
request for an extension of the briefing deadline was denied,
and (2) the brief was received 33 days late. Neither basis sup-
ports the Board’s decision.
First, the mere fact that the Board denied a second exten-
sion request cannot justify the rejection of a late brief. Alt-
hough the agency’s regulation does not explicitly limit the
amendment took effect. See 85 Fed. Reg. 81,588, 81,588 (Dec. 16, 2020). At
present, the amendment’s enforcement is preliminarily enjoined. See Cen-
tro Legal de la Raza v. Exec. Off. for Immigr. Rev., 524 F. Supp. 3d 919 (N.D.
Cal. 2021).

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No. 21-1804 7
number of extensions of the briefing deadline, the Board’s
Practice Manual makes clear that a second extension request
will usually be denied. Yet the regulation does say that the
Board “may consider a brief that has been filed out of time.”
8 C.F.R. § 1003.3(c)(1) (2020) (emphasis added). Thus, the
Board’s rules envision that a late brief may be accepted even
though a second extension of the briefing deadline was de-
nied. It was nonsensical for the Board to deny Oluwajana per-
missible relief because he was not first granted a different
kind of relief that the Board rarely permits. We will not sus-
tain a decision based on the Board’s interpretation of its rules
that causes “unreasonable, unfair, and absurd results.” Chow-
dhury, 241 F.3d at 853.
Next, and more obviously, the Board clearly erred in find-
ing that Oluwajana submitted his brief 33 days late. After the
Board granted the initial request to extend the briefing dead-
line, the due date was February 24, 2021, not February 3. So,
when Oluwajana submitted his brief on March 8, it was only
12 days past due, not the month and more stated in the
Board’s order. The Board abuses its discretion when it exer-
cises that discretion based on factual determinations “con-
trary to the detailed evidence in the record.” Siddiqui v. Holder,
670 F.3d 736, 746 (7th Cir. 2012).
To its credit, the government does not defend the Board’s
decision. Rather, without confessing error, the government
urges us to remand the matter for the Board to reconsider
whether to accept Oluwajana’s brief. When the government
requests a general remand and that request is opposed by the
petitioner, we will grant the request “only when there is a per-
suasive reason to do so.” W.G.A. v. Sessions, 900 F.3d 957, 963
(7th Cir. 2018). We discern no such reason here.

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8 No. 21-1804
This is not a case where the Board’s decision to reject a late
brief turned on questions of disputable fact, such as whether
an individual in removal proceedings received notice of the
Board’s briefing schedule, see Dakaj, 580 F.3d at 482–84, or
whether lateness should have been excused based on a total-
ity of subjective factors, like a petitioner’s “pro se status, edu-
cation, [or] language skills,” Gutierrez-Almazan v. Gonzales,
491 F.3d 341, 344 (7th Cir. 2007). In such cases, we remanded
because the Board had yet to fulfill its obligation “to consider
all relevant information,” and we were persuaded that the
Board could—“at least in the first instance”—potentially jus-
tify its rejection of a brief. Dakaj, 580 F.3d at 483–84.
In the present case, the salient facts are undisputed. The
government failed to provide Oluwajana’s counsel with a
copy of his immigration file—including the transcripts of im-
migration court proceedings—until February 16, 2021. This
was almost two weeks after the initial deadline set by the
Board to file an administrative brief, a brief that could not
have been filed without review of the file. Yet, less than three
weeks after the EOIR finally provided a copy of the file, coun-
sel drafted a brief and filed it with the Board, a mere 12 days
past the revised due date. That is, the delay resulted princi-
pally (if not entirely) from the tardiness with which the gov-
ernment fulfilled its obligation to provide Oluwajana’s coun-
sel critical information. And counsel, in turn, acted expedi-
tiously when that information was received.
On these facts, any reasonable exercise of discretion re-
quired acceptance of Oluwajana’s brief. Thus, we will not or-
der a general remand solely for the Board to consider again
the uncontested record already before it. At the same time, we
decline to address Oluwajana’s allegations of error by the IJ.

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No. 21-1804 9
Those contentions are best addressed in the first instance by
the Board, which will now have the benefit of Oluwajana’s
briefed arguments.
We are mindful that the abuse-of-discretion standard is
deferential and that deadlines are necessary for the operation
of the immigration system, which we have acknowledged is
“overburdened.” Vidinski v. Lynch, 840 F.3d 912, 918 (7th Cir.
2016). But the Board’s own rules contemplate that, deadlines
notwithstanding, it is sometimes appropriate to accept a late-
filed brief. Based on the present circumstances, we conclude
that this is one of those times.
The Board clearly abused its discretion in denying Olu-
wajana’s motion to file his brief out of time; the brief must be
accepted. Accordingly, we GRANT the petition for review,
VACATE the Board’s order, and REMAND for further pro-
ceedings consistent with this opinion.

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