United States v. Luna

United States Court of Appeals
For the First Circuit

No. 05-1122

UNITED STATES OF AMERICA,

Appellee,

v.

DAGOBERTO LUNA,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF RHODE ISLAND

[Hon. Mary M. Lisi, U.S. District Judge]

Before

Lipez, Circuit Judge,
Coffin, Senior Circuit Judge,
and Carter,* Senior District Judge.

Edward C. Roy, Assistant Federal Public Defender, for
appellant.
Robert Clark Corrente, United States Attorney, with whom
Donald C. Lockhart and Luis M. Matos, Assistant United States
Attorneys, were on brief, for appellee.

February 9, 2006

*
Of the District of Maine, sitting by designation.
 LIPEZ, Circuit Judge. This case requires us to analyze

the statutory provision (8 U.S.C. § 1326(d)) that defines the

circumstances under which a defendant charged with illegally

reentering the United States after deportation may collaterally

attack the validity of the removal order.1 The defendant,

Dagoberto Luna, appeals from the district court's denial of his

motion to dismiss his indictment for illegal reentry. The district

court held that the defendant did not meet the requirements of

§ 1326(d). We affirm.

I.

A. Luna's Background and Deportation Proceedings

Luna, a citizen of the Dominican Republic, entered the

United States as a 5-day-old lawful permanent resident in 1973.

His immediate family members, including his mother, father, and

siblings, all live in the United States. Luna spent most of his

childhood in Rhode Island, where he attended school until the 9th

grade. Since that time, he has lived in New York and Rhode Island.

On April 9, 1993, at age 20, Luna was ordered deported

after he was convicted in state court of third degree grand

larceny. He returned to the United States at some point

thereafter. On January 22, 1996, Luna pled guilty in state court

to second degree assault. He was sentenced to three to six years

1
We use the terms "removal" and "deportation" interchangeably in
this opinion.

-2-
imprisonment. While he was serving his sentence, the Immigration

and Naturalization Service ("INS") issued an Order to Show Cause

charging that Luna was deportable on several grounds, including his

assault conviction and his previous deportation order and reentry.

Given "serious problems" regarding the validity of the previous

deportation order,2 the Immigration Judge ("IJ") found that Luna

was deportable on the sole ground of being an alien convicted of an

aggravated felony, see Immigration and Nationality Act ("INA")

§ 237(a)(2)(A)(iii), 8 U.S.C. § 1227(a)(2)(A)(iii) (formerly INA

§ 241(a)(2)(A)(iii), 8 U.S.C. § 1251 (redesignated 1996)), based on

his second degree assault conviction.

During his hearing before the IJ, Luna applied for

discretionary relief, requesting a waiver of deportation under

former INA § 212(c). 8 U.S.C. § 1182(c) (repealed 1996).3 The IJ

2
The IJ in Luna's second deportation hearing noted that both Luna
and the INS agreed that there were "serious problems with the
respondent's original deportation hearing," because "the respondent
was deported as having been convicted of two crimes involving moral
turpitude . . . which was not shown in the respondent's case."
Specifically, the IJ noted that "one of the underlying crimes,
burglary in the third degree, is not necessarily a crime involving
moral turpitude, unless it can be shown what specific crime the
burglary was meant to commit" and that the INS had failed to
establish its case. In addition, the IJ noted that "as a matter of
equity, [Luna] testified that he did not appear in court because
his child died immediately before the immigration hearing . . . and
therefore his attendance there was impossible."
3
Former § 212(c) provided that "[a]liens lawfully admitted for
permanent residence who temporarily proceeded abroad voluntarily
and not under an order of deportation, and who are returning to a
lawful unrelinquished domicile of seven consecutive years, may be
admitted in the discretion of the Attorney General . . . . [T]his

-3-
did not consider the merits of Luna's application for relief,

stating in his oral decision that "the respondent is statutorily

barred from this and any other forms of relief from deportation"

under the Attorney General's decision in In re Soriano, 21 I. & N.

Dec. 516 (BIA 1996, A.G. 1997).4

In Soriano, the Attorney General determined that recent

statutory amendments to the INA prevented all individuals with

"aggravated felony" convictions in removal proceedings from

obtaining discretionary relief from deportation. See id. at 533-

40; see also Anti-Terrorism and Effective Death Penalty Act of 1996

("AEDPA"), Pub. L. No. 104-132, 110 Stat. 1214 (1996) (codified in

various titles); Illegal Immigration Reform and Immigrant

Responsibility Act of 1996 ("IIRIRA"), Pub. L. No. 104-208, 110

Stat. 3009 (1996) (codified in various titles).5 Although Luna

subsection shall not apply to an alien who has been convicted of
one or more aggravated felonies and has served for such felony or
felonies a term of imprisonment of at least 5 years." 8 U.S.C.
§ 1182(c)(repealed 1996). By its terms, the statute appears to
have applied only to lawful permanent residents "returning" to the
United States and facing exclusion. However, the statute has been
interpreted to be applicable to any lawful permanent resident,
facing exclusion or deportation, who met its eligibility
requirements. See Gomes v. Ashcroft, 311 F.3d 43, 44-45 (1st Cir.
2002).
4
Decisions by the Attorney General in immigration proceedings are
binding on the Board of Immigration Appeals and Immigration Judges.
See 8 C.F.R. § 1003.1(g) (stating that "decisions of the Attorney
General . . . shall be binding . . . [and] shall serve as
precedents in all proceedings involving the same issue or issues").
5
AEDPA amended INA § 212(c) to preclude relief for immigrants
facing deportation due to an "aggravated felony." IIRIRA

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pled guilty to second degree assault before the relevant provisions

of AEDPA and IIRIRA went into effect, the IJ concluded that, under

Soriano, Luna could not apply for discretionary relief.

Luna, who was represented by a non-lawyer "accredited

representative,"6 appealed the IJ decision to the Board of

Immigration Appeals ("BIA"). On June 10, 1998, the BIA affirmed,

also relying on Soriano, telling Luna that he was "statutorily

ineligible for [§ 212(c)] relief." Luna did not appeal the

agency's decision in federal court. On November 8, 1999, he was

deported for a second time.

B. St. Cyr and Eligibility for INA § 212(c) Relief

In 2001, the Supreme Court corrected the Attorney

General's misapplication of law. See INS v. St. Cyr, 533 U.S. 289

(2001). The Supreme Court emphasized that "the class of aliens

whose continued residence in this country has depended on their

eligibility for § 212(c) relief is extremely large," and that the

retroactive repeal of such relief "would surely be contrary to

familiar considerations of fair notice, reasonable reliance, and

settled expectations." Id. at 295-96, 323 (citations and internal

completely repealed § 212(c) and created a new form of
discretionary relief, "cancellation of removal," which also was not
available for immigrants with "aggravated felony" convictions. See
INA § 240A, 8 U.S.C. § 1229b(a).
6
Under certain conditions, non-lawyers, including "accredited
representatives" of approved non-profit organizations, may
represent individuals in removal proceedings. See 8 C.F.R. §§
292.1, 292.2.

-5-
quotation marks omitted). The Court concluded that the repeal of

§ 212(c) relief did not apply retroactively to individuals who had

pled guilty to a criminal charge prior to the effective date of the

repeal. Id. at 326.

After St. Cyr was decided, the government changed its

position on the availability of § 212(c) relief for individuals who

pled guilty or nolo contendere to crimes before the effective date

of AEDPA and IRRIRA. In 2004, the government implemented

procedures for immigrants to reopen their removal cases in light of

St. Cyr. See 8 C.F.R. § 1003.44. However, the procedures were not

available for immigrants who had already "departed" the country.

See 8 C.F.R. § 1003.44(k).

C. Luna's Indictment for Reentry and the District Court Decision

At some point after his second deportation, Luna

reentered the United States. On November 21, 2003, Luna was

indicted for illegally reentering the United States without the

express permission of the Attorney General, in violation of 8

U.S.C. §§ 1326(a) and (b)(2). He filed a motion to dismiss the

indictment, pursuant to 8 U.S.C. § 1326(d),7 arguing that his

7
Under the statute, a defendant may challenge the validity of a
deportation order that serves as the basis for an indictment for
illegal reentry. See infra, Part III(A) (describing 8 U.S.C.
§ 1326(d)).

-6-
deportation was fundamentally unfair and thus could not serve as

the basis for his illegal reentry indictment.8

In its Memorandum and Decision of April 13, 2004 ("April

13 Decision"), the district court denied Luna's motion to dismiss,

holding that he failed to establish, as required by 8 U.S.C.

§ 1326(d)(3), that the IJ's failure to adjudicate his § 212(c)

application prejudiced him. Luna filed a motion asking the

district court to reconsider. On June 1, 2004, the district court

issued a second Memorandum and Decision ("June 1 Decision") again

denying the motion to dismiss. The court held that, in addition to

Luna’s failure to demonstrate prejudice, Luna also failed to

establish the requirement under 8 U.S.C. § 1326(d)(2) that his

underlying deportation proceedings improperly deprived him of

judicial review. Luna appealed.

III.

The underlying facts are not in dispute, and we review

the district court's legal conclusions de novo. See United States

8
During the hearing on the motion to dismiss, the district court
questioned whether the first deportation order, issued in 1993,
could serve as a basis for the indictment for illegal reentry.
However, the district court did not resolve the issue. In response
to the district court's questioning during the hearing, the
government stated that it focused on the second order of
deportation because it believed that the first order of deportation
was defective. On appeal, both the government and the defendant
continue to focus solely on the second order of deportation,
raising no arguments regarding the possible validity of the first
deportation order as a basis for the indictment. Accordingly, our
review will focus on the second order of deportation.

-7-
v. Loaisiga, 104 F.3d 484, 486 (1st Cir. 1997) (applying de novo

standard of review to district court's decision to grant motion to

dismiss an indictment for illegal reentry under a prior version of

8 U.S.C. § 1326).

The government argues that we should review the district

court's prejudice determination for clear error. While we review

factual findings under a clear error standard, the prejudice

analysis in this case involves the application of law to undisputed

facts and is part of an inquiry to determine whether the defendant

has established the fundamental unfairness of his deportation

hearing. Under these circumstances, we agree with our sister

circuits that a district court's determination of whether a

defendant has established prejudice pursuant to 8 U.S.C.

§ 1326(d)(3) is subject to de novo review. See United States v.

Scott, 394 F.3d 111, 116-17 (2d Cir. 2005) (applying de novo review

to district court's determination of whether defendant has

established prejudice under 8 U.S.C. § 1326(d)(3)); United States

v. Aguirre-Tello, 353 F.3d 1199, 1204 (10th Cir. 2004) (en banc)

(same); United States v. Ubaldo-Figueroa, 364 F.3d 1042, 1047 (9th

Cir. 2003) (same).

A. Mendoza-Lopez and 8 U.S.C. § 1326

Under 8 U.S.C. § 1326(a), it is a crime for an individual

who has been deported, removed, excluded, or denied admission to

enter the United States unless he or she has the prior approval of

-8-
the Attorney General or shows that no such approval was needed.

Section 1326(b) specifies enhanced penalties for illegal reentry

based on the person's criminal history.

In United States v. Mendoza-Lopez, 481 U.S. 828 (1987),

the Supreme Court held that a person who is prosecuted for illegal

reentry based on a previous order of deportation must have

meaningful review of the validity of his or her deportation order.

The defendants in Mendoza-Lopez, having been indicted for illegally

reentering the United States, argued that their previous

deportation proceedings were fundamentally unfair because the IJ

had failed to inform them adequately of their eligibility for

"suspension of deportation," a form of discretionary relief. See

id. at 831-32. The Supreme Court concluded that the defendants'

motions to dismiss their indictments should be granted because they

had been "deprived of their rights to appeal [their removal

orders], and of any basis to appeal since the only relief [from

deportation] for which they would have been eligible was not

adequately explained to them." Id. at 842. As the Court explained,

"where a determination made in an administrative proceeding is to

play a critical role in the subsequent imposition of a criminal

sanction, there must be some meaningful review of the

administrative proceeding." Id. at 837-38 (emphasis in original).

Congress essentially codified the Mendoza-Lopez decision

as 8 U.S.C. § 1326(d). See United States v. Wilson, 316 F.3d 506,

-9-
515 n.1 (4th Cir. 2003) (Motz, J., concurring) (discussing the

legislative history of § 1326(d)). Section 1326(d) provides:

In a criminal proceeding under this section,
an alien may not challenge the validity of the
deportation order . . . unless the alien
demonstrates that --
(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.

These elements are in the conjunctive; therefore, a defendant must

satisfy all of them to successfully attack his removal order. See

United States v. Roque-Espinoza, 338 F.3d 724, 728 (7th Cir. 2003);

Wilson, 316 F.3d at 509; United States v. Fernandez-Antonia, 278

F.3d 150, 157 (2d Cir. 2002); United States v. Lepore, 304 F. Supp.

2d 183, 186 (D. Mass. 2004).

B. Application of § 1326(d) to Luna’s Case

The interpretation of this statute presents us with

several difficult issues of first impression. While the parties

agree that Luna has met the administrative exhaustion requirement

of 8 U.S.C. § 1326(d)(1),9 they disagree about whether Luna has met

9
Under 8 U.S.C. § 1326(d)(1), a defendant who seeks to challenge
the validity of his deportation order must have exhausted the
administrative remedies during his removal proceedings or show that
an appropriate exception applies. See United States v. Sosa, 387
F.3d 131, 136-37 (2d Cir. 2004) (explaining the scope of the 8
U.S.C. § 1326(d)(1) requirement); Lepore, 304 F. Supp. 2d at 192

-10-
the other statutory requirements. The government argues that we

can affirm the district court's order on either of its stated

grounds –- that Luna was not deprived of judicial review under

§ 1326(d)(2) or that Luna has not established prejudice as part of

the fundamental unfairness inquiry under § 1326(d)(3). The

government also argues that, alternatively, we can affirm the

district court's order because the defendant failed to establish

that the errors in his hearing, even if prejudicial, rendered his

deportation order fundamentally unfair under § 1326(d)(3). Luna

argues that he meets all the statutory requirements. We address

these arguments and discuss the second and third prongs of

§ 1326(d). However, because we conclude that Luna has not

established prejudice under 8 U.S.C. § 1326(d)(3), we need not

ultimately resolve all the statutory issues.

1. Section 1326(d)(2): Deprivation of Judicial Review

Under 8 U.S.C. § 1326(d)(2), a defendant who seeks to

challenge the validity of his deportation order must demonstrate

that "the deportation proceedings at which the order was issued

improperly deprived the alien of the opportunity for judicial

review." In its June 1 Decision, the district court held that Luna

did not meet this requirement because he had an opportunity for

(same). We agree with the parties and the district court that Luna
met this requirement by appealing the IJ's decision to the BIA in
his case. See United States v. Perez, 330 F.3d 97, 100-01 (2d Cir.
2003) (indicating that an appeal of an IJ's decision or a denial of
a motion to reopen to the BIA will satisfy 8 U.S.C. § 1326(d)(1)).

-11-
judicial review -- a writ of habeas corpus -- but failed to pursue

it.10 Luna argues that the IJ and the BIA effectively deprived him

of judicial review by failing to properly inform him of his

eligibility for relief, adjudicate his application for relief, or

inform him of any right to appeal.

We have not previously interpreted § 1326(d)(2).11

10
The availability of habeas review was a contested issue at the
time of Luna's deportation proceedings. AEDPA and IIRIRA amended
the INA to statutorily bar people with certain criminal convictions
from seeking review of their final orders of removal through a
petition for review to the courts of appeals. See 8 U.S.C.
§ 1252(a)(2)(c) ("[N]o court shall have jurisdiction to review any
final order of removal against an alien who is removable by reason
of having committed a criminal offense [under certain sections of
the INA] . . . .") (amended 2005). During the time of Luna's
deportation proceedings, the government was advancing the argument
that no court had jurisdiction over such cases, even if the
individual filed a writ of habeas corpus. The Supreme Court
eventually rejected this argument. See St. Cyr, 533 U.S. at 314
(concluding that provisions barring certain people from pursuing
direct review of their orders of removal do not apply to habeas
review under 28 U.S.C. § 2241).
11
We reject the government's suggestion that our precedent
interpreting Mendoza-Lopez resolves this issue. Prior to the
enactment of § 1326(d), we applied Mendoza-Lopez and held that
defendants who deliberately and voluntarily withdrew their right to
administratively appeal an IJ's decision to the BIA under the
advice of counsel cannot show that they were deprived of meaningful
judicial review. See United States v. Smith, 36 F.3d 128, 130-31
(1st Cir. 1994) (no deprivation of meaningful review where
defendant under advice of counsel signed a motion withdrawing his
appeal and provided no evidence that his waiver was involuntary);
United States v. Smith, 14 F.3d 662, 664-65 (1st Cir. 1994) (no
deprivation of meaningful review where defendant under advice of
counsel filed an appeal but then later voluntarily withdrew his
appeal); United States v. Vieira-Candelario, 6 F.3d 12, 15 (1st
Cir. 1993) (same). These cases are distinguishable from the
instant case because the defendants in those cases, unlike Luna,
chose, on the advice of legal counsel, to affirmatively abandon
their appeals. See Lepore, 304 F. Supp. 2d at 195 (discussing

-12-
However, Mendoza-Lopez provides some guidance. The Supreme Court

held that an IJ's failure to adequately explain the availability of

relief, resulting in an uninformed waiver of the right to appeal,

was an error that deprived the individuals in that case of their

opportunity for judicial review. Mendoza-Lopez, 481 U.S. at 842.

Other than this specific holding, however, the Supreme Court has

declined to further "enumerate which procedural errors are so

fundamental that they may functionally deprive the alien of

judicial review." See id. at 839 n.17.

In this case, the government essentially argues that, as

the district court concluded, the availability of judicial review

through a writ of habeas corpus is fatal to the defendant's claim

under § 1326(d)(2). However, the conclusions of the few courts

that have considered this argument have not been uniform. Compare

Sosa, 387 F.3d at 137 ("[T]he fact that [a chance to file a habeas

petition] technically existed does not necessarily mean that [the

defendant] had an 'opportunity for judicial review' within the

meaning of Section 1326(d)(2).") and United States v. Copeland, 376

F.3d 61, 68 (2d Cir. 2004) (noting that "[i]n Mendoza-Lopez itself,

habeas review was apparently available to the aliens, yet the Court

held that they were deprived of judicial review") with Roque-

Espinoza, 338 F.3d at 729 ("Even though [the defendant] may have

had good reason for thinking that he was not eligible for

cases).

-13-
discretionary relief from removal, because the IJ had so informed

him, he should have realized that avenues of judicial review were

available to him.").

Given the uncertainty in the law on this issue, we turn

to § 1326(d)(3). Because, as we explain below, we conclude that

Luna has not established prejudice, we need not decide whether,

under § 1326(d)(2), the errors in Luna's case functionally deprived

him of judicial review despite the availability of habeas review.

2. Section 1326(d)(3): Fundamental Unfairness

A defendant who seeks to challenge the validity of his

deportation order must demonstrate that "the entry of the order was

fundamentally unfair." 8 U.S.C. § 1326(d)(3). Under this prong,

courts uniformly require a showing of procedural error and

prejudice. See, e.g., Aguirre-Tello, 353 F.3d at 1207-08; Perez,

330 F.3d at 103-04; Ubaldo-Figueroa, 364 F.3d at 1050; Wilson, 316

F.3d at 510.

Courts disagree, however, on what type of procedural

error, if prejudicial, would result in a fundamentally unfair

deportation order under the statute. The Third, Fourth, and Fifth

Circuits have held that § 1326(d)(3) requires a showing that the

error in the deportation hearing has resulted in a deprivation of

a liberty or property interest. See United States v. Torres, 383

F.3d 92, 103 (3rd Cir. 2004); Wilson, 316 F.3d at 510; United

States v. Lopez-Ortiz, 313 F.3d 225, 230 (5th Cir. 2002). These

-14-
courts have rejected the argument that an agency's failure to

adequately inform an immigrant of his or her eligibility for

§ 212(c) relief can establish fundamental unfairness, because an

applicant has no liberty or property interest in discretionary

relief. See Torres, 383 F.3d at 103 ("[B]ecause discretionary

relief is necessarily a matter of grace rather than of right,

aliens do not have a due process liberty interest in consideration

for such relief."); Wilson, 316 F.3d at 510 ("[S]ection 212(c) does

not create an entitlement, but is rather completely discretionary

in nature."); Lopez-Ortiz, 313 F.3d at 230 ("Because eligibility

for § 212(c) relief is not a liberty or property interest

warranting due process protection, we hold that the Immigration

Judge's error in failing to explain Lopez-Ortiz's eligibility does

not rise to the level of fundamental unfairness.").

The Second and Ninth Circuits have taken a different

approach. These courts have held that an agency's violation of the

procedural protections in its statute or regulations, if

prejudicial to the person facing deportation, can demonstrate

fundamental unfairness under 8 U.S.C. § 1326(d)(3). See Copeland,

376 F.3d at 71-73; Ubaldo-Figueroa, 364 F.3d at 1042. They

conclude, therefore, that an agency's failure to adequately inform

an immigrant of his or her eligibility for § 212(c) relief, if

prejudicial, can render the deportation fundamentally unfair. See

Copeland, 376 F.3d at 72 ("The decisions holding that a failure to

-15-
inform an alien about Section 212(c) relief cannot be a fundamental

error collapse [the] distinction [between a right to seek relief

and the right to that relief itself] . . . . The issue, therefore,

is not whether Section 212(c) relief is constitutionally mandated,

but whether a denial of an established right [under agency

regulations] to be informed of the possibility of such relief can,

if prejudicial, be a fundamental procedural error."); Ubaldo-

Figueroa, 364 F.3d at 1042 ("The requirement that the IJ inform an

alien of his or her ability to apply for relief from removal is

'mandatory,' and 'failure to so inform the alien [of his or her

eligibility for relief from removal] is a denial of due process

that invalidates the underlying deportation proceedings.'")

(quoting United States v. Muro-Inclan, 249 F.3d 1180, 1183 (9th

Cir. 2001)).

Although we have not interpreted § 1326(d)(3), we have

analyzed whether a deportation order was "fundamentally flawed" in

the context of a defendant's challenge to his indictment for

illegal reentry after Mendoza-Lopez. Loaisiga, 104 F.3d at 484-85.

The defendant in Loaisiga claimed that he was not adequately

advised of his right to self-obtained counsel. Id. We stated that

we would "assume without deciding that it would be a fundamental

flaw under Mendoza-Lopez to fail to advise one threatened with

deportation of his statutory right to self-obtained counsel." Id.

at 486. However, we found that the IJ complied with all relevant

-16-
statutory and regulatory requirements. See id. at 485-86. We then

stated that "it has been left primarily to Congress and to INS

regulations to dictate the course of proceedings -- which both

bodies have done in some detail . . . . Courts normally require

nothing more in the way of procedural protection, except to prevent

flagrant abuses -- normally those rising to the level of due

process violations." Id. at 486 (emphasis in original). Having

found no statutory or regulatory violations, we asked whether the

IJ violated the defendant's constitutional rights.

We did not resolve all of the constitutional issues,

however.12 We held that, "for a collateral attack on a now-final

deportation order, the defendant must show prejudice." Id. at 487

(emphasis in original). Because Loaisiga had not demonstrated

prejudice, we held that he could not collaterally attack the

validity of his deportation order.

12
We noted that the IJ had repeatedly advised Loaisiga of his right
to self-obtained counsel and had given him three weeks to seek an
attorney prior to his deportation hearing. See Loaisiga, 104 F.3d
at 486. In light of those facts, we rejected Loaisiga's claim that
the IJ violated due process by failing to advise Loaisiga again of
his right to counsel at the beginning of the hearing. Id.
("[A]bsent some signal from Loaisiga -- such as a plausible request
for a further delay -- we do not think that it was even close to a
due process violation for the immigration judge to move on to the
merits."). However, we did not decide whether "due process
required that Loaisiga be advised again at the close of the []
hearing of his right to obtain his own counsel for an appeal." Id.
at 487 (emphasis in original) (noting that "a respondent's
inclination to appeal might be affected by being told (again) that
he could be represented by counsel" but concluding that "this
interesting issue need not be decided here").

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 In this case, the IJ failed to inform Luna of his

eligibility for § 212(c) relief, provide him with an opportunity to

apply for that relief, or adjudicate his application for relief.13

The government argues that the errors do not render the entry of

the deportation order fundamentally unfair under 8 U.S.C.

§ 1326(d)(3). However, as was the case in Loaisiga, we do not have

to resolve the question of whether the agency's errors in this case

would, if prejudicial, render the deportation proceedings

fundamentally unfair. We agree with the district court's holding

that Luna has not demonstrated prejudice.

As discussed above, the facts of this case are

undisputed, and we review de novo the district court's

determination that Luna has failed to establish prejudice. The

standard for prejudice in this context is "a reasonable likelihood

that the result would have been different if the error in the

deportation proceeding had not occurred.” Loaisiga, 104 F.3d at

13
See 8 C.F.R. § 1240.11(a)(2) ("The immigration judge shall inform
the alien of his or her apparent eligibility to apply for any of
the benefits [of relief from deportation] enumerated in this
chapter and shall afford the alien an opportunity to make an
application during the hearing.") (emphasis added); 8 C.F.R. §
242.17(a) (amended 1998) ("The immigration judge shall inform the
respondent of his or her apparent eligibility to apply for any of
the benefits enumerated in this paragraph and shall afford the
respondent an opportunity to make application therefor during the
hearing."); 8 C.F.R. § 212.3(e) ("An application for the exercise
of discretion under section 212(c) of the Act may be . . .
submitted in proceedings before an Immigration Judge. . . . Such
application shall be adjudicated by the Immigration Judge.")
(emphasis added).

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487.14 In other words, the defendant must show that, if the IJ had

adjudicated his § 212(c) application, there is a reasonable

likelihood that he would have received relief from deportation.

Given the undisputed factual findings of the district

court, we therefore must consider how the IJ itself would consider

these factors when adjudicating a § 212(c) waiver application. In

its decisions, the agency has "developed criteria, comparable to

common-law rules, for deciding when deportation is appropriate."

St. Cyr, 533 U.S. at 295 n.5 (citing Matter of Marin, 16 I. & N.

Dec. 581 (BIA 1978)). These criteria have included "the

seriousness of the offense, evidence of either rehabilitation or

recidivism, the duration of the alien's residence, the impact of

deportation on the family, the number of citizens in the family,

and the character of any service in the Armed Forces." Id. Other

factors include arrival in the United States as a child, history of

employment, property or business ties, community service, and

evidence of good character. Marin, 16 I. & N. Dec. at 584-85.

After noting all the factors in an individual's case, an IJ "must

balance the adverse factors evidencing an alien's undesirability .

. . with the social and humane considerations presented in his

behalf." Id. at 584.

14
There 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, Loaisiga, 104
F.3d at 488, but no court has applied that concept to the context
of the failure to adjudicate an application for § 212(c) relief.

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 Individuals with particularly lengthy or violent criminal

histories are generally required to show particularly strong

countervailing equities or rehabilitation to obtain § 212(c)

relief.15 See Scott, 394 F.3d at 120-21. However, criminal history

is not a per-se bar to relief.16 See Lepore, 304 F. Supp. 2d at 199

("It is important to remember that, by definition, 'aggravated

felons' are eligible for relief, so the fact that [an applicant for

§ 212(c) relief] is a convicted criminal cannot be dispositive.").

15
The BIA has explained that, "as the negative factors grow more
serious, it becomes incumbent upon the alien to introduce
additional offsetting favorable evidence, which in some cases may
have to involve unusual or outstanding equities." Marin, 16 I. & N.
Dec. at 585. A single criminal act, depending on the seriousness
of the underlying conduct, or "a succession of criminal acts, which
together establish a pattern of serious criminal misconduct" can
trigger this heightened requirement. Matter of Buscemi, 19 I. & N.
Dec. 628, 633 (BIA 1988). While evidence of rehabilitation is one
factor often considered in this context, the BIA has indicated that
an IJ must consider the circumstances faced by the applicant for
§ 212(c) relief, particularly the difficulties that incarceration
may pose. See In re Arreguin De Rodriguez, 21 I. & N. Dec. 38, 40
(BIA 1995) ("A clear showing of reformation is not an absolute
prerequisite to a favorable exercise of discretion in every section
212(c) application involving an alien with a criminal record.
Section 212(c) applications involving convicted aliens must be
evaluated on a case-by-case basis, with rehabilitation a factor to
be considered in the exercise of discretion. . . . We recognize
the difficulties an incarcerated alien faces in demonstrating
convincing efforts towards rehabilitation. . . . [A]ny efforts
will be considered, and the applicant is not barred automatically
from discretionary relief by her incarceration." (citations
omitted)).
16
Indeed, we have noted that the grant of discretionary relief for
individuals with criminal convictions "was not rare: in the years
immediately preceding the [statutory repeal of § 212(c) relief for
'aggravated felons'], over half the applications were granted."
Mattis v. Reno, 212 F.3d 31, 33 (1st Cir. 2000).

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Furthermore, only criminal history that occurred prior to the

challenged deportation hearing should be considered when assessing

prejudice in the § 1326(d) context. See Scott, 394 F.3d at 118

("[Section 1326(d)(3)]’s focus on the 'entry' of the order suggests

a temporal limitation on the district court’s inquiry. In other

words, the statute itself indicates that . . . the only pertinent

issue is whether entry of the deportation order . . . prejudiced

[the defendant] -- regardless of [the defendant]’s potential

deportability for some later crimes.”).

Because of the multitude of factors involved in this

inquiry, the “[r]esolution of the prejudice issue in the Section

1326(d)(3) context is somewhat akin to a trial within a trial. . .

. The court must first obtain all of the facts relevant to the

particular alien and then apply standards established under Section

212(c) to those facts . . . .” Copeland, 376 F.3d at 73-74.

In this case, the district court heard arguments on the

motion to dismiss and considered the entire record.17 The district

court noted six factors that could weigh in favor of Luna’s case,

including that (1) over fifty percent of those who apply for

§ 212(c) relief are granted such relief; (2) defendants with felony

records are eligible for § 212(c) waivers; (3) Luna was abused as

a child for ten years, (4) most of Luna's family members, including

17
The defendant, through counsel, did not request to submit any
additional evidence in support of his prejudice argument.

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his parents and five siblings, were present in the United States at

the time of his deportation hearing; (5) Luna had an opportunity to

rehabilitate himself in prison; and (6) Luna has lived in the

United States for the majority of his life.

The district court then considered three factors weighing

against Luna’s case, including that (1) Luna returned to the United

States in defiance of a court order (referencing Luna's first

deportation hearing and reentry); (2) Luna admitted to convictions

for grand larceny and assault (for the brutal assault of a twelve-

year-old child) in his deportation hearings18 and (3) Luna's lack

of specific employment history. The court concluded that Luna

failed to establish prejudice, noting that "[a]lthough Defendant

recites several factors he believes support his application for

section 212(c) relief, he falls short of convincing this Court that

those favorable factors outweigh the adverse ones, especially

Defendant's violent criminal history."

As a preliminary matter, we note that Luna’s first

deportation order and reentry should not factor into the prejudice

analysis, given the agency’s recognition of the “serious errors”

made in his first deportation proceedings. The IJ in Luna’s second

deportation hearing was so troubled by the errors that he did not

consider the first deportation hearing and reentry as grounds for

18
Along with these convictions, Luna's criminal history prior to his
second deportation includes convictions for possession of a stolen
vehicle and burglary.

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deportation. Given this determination, it is unlikely that the IJ

would have considered that reentry in an adjudication of Luna's

§ 212(c) application.

Putting aside that factor, however, we nonetheless agree

with the district court’s conclusion. Luna has a serious criminal

history, including numerous offenses and a violent crime against a

child. Although he asserts that he has had the opportunity to

rehabilitate himself, he fails to specify any evidence of

rehabilitation or good character. Luna lacks a history of steady

employment and points to no evidence of positive contributions to

society. Furthermore, although Luna's parents and siblings are in

this country, Luna fails to describe his relationship with them and

the extent of the hardship that they will face if he is deported.

We have carefully considered the favorable equities that Luna does

assert, particularly his lengthy residency here since infancy.

However, on the balance, we conclude that there is no reasonable

likelihood that the agency would have granted a waiver in his case.

While none of the aforementioned factors, taken alone, would

necessarily doom Luna's application, we conclude that his lengthy

criminal history, the violent nature of his criminal activity, and

the relative lack of positive equities eliminate any reasonable

likelihood that he would have received a grant of relief.

Because Luna has failed to demonstrate prejudice under

§ 1326(d), the district court properly denied his motion to dismiss

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the indictment for illegal reentry. The decision of the district

court is affirmed.

So ordered.

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