[DO NOT PUBLISH]

IN THE UNITED STATES COURT OF APPEALS

FOR THE ELEVENTH CIRCUIT

________________________

No. 18-15345

Non-Argument Calendar

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D.C. Docket No. 1:18-cr-20785-PCH-1

UNITED STATES OF AMERICA, 

 Plaintiff-Appellee,

 versus

RAFAEL ERENIO IZQUIERDO, 

 Defendant-Appellant.

________________________

Appeal from the United States District Court

for the Southern District of Florida

________________________

(April 5, 2021)

Before GRANT, LUCK, and EDMONDSON, Circuit Judges.

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PER CURIAM: 

Rafael Izquierdo appeals his conviction after pleading guilty to unlawful 

procurement of naturalization and citizenship, in violation of 18 U.S.C. § 1425(a). 

No reversible error has been shown; we affirm.

Izquierdo is a native of Cuba who became a lawful permanent resident of the 

United States and a naturalized citizen on 30 September 2016. As part of the 

naturalization process, Izquierdo completed an Immigration Form N-400, 

Application for Naturalization (“Application”). By signing the Application, 

Izquierdo certified under penalty of perjury that the information on the Application 

was true. In response to Part 11, Question 22 on the Application -- “[h]ave you 

EVER committed, assisted in committing, or attempted to commit, a crime or 

offense for which you were NOT arrested?” -- Izquierdo answered “No.” 

Izquierdo confirmed this answer two more times: during an August 2016 interview 

for naturalization, and on his Immigration Form N-455, Notice of Naturalization 

Oath Ceremony. 

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In 2017, Izquierdo was convicted after pleading guilty to conspiracy to 

commit wire fraud: a conspiracy that was ongoing between January 2014 and

January 2017. 

Given the dates of the wire fraud conspiracy -- and contrary to Izquierdo’s 

responses during his naturalization proceedings in 2016 -- Izquierdo had 

committed and was continuing to commit crimes and offenses for which he had not 

been arrested. Based on Izquierdo’s false representations under oath during the 

naturalization process, Izquierdo was charged with unlawful procurement of 

naturalization and citizenship, in violation of 18 U.S.C. § 1425(a). 

I.

On appeal, Izquierdo contends his guilty plea was not entered knowingly 

and voluntarily. As a result, he says the plea proceedings deprived him of due 

process and failed to comply with the requirements of Fed. R. Crim. P. 11. 

Because Izquierdo challenges the adequacy of his plea proceedings for the 

first time on appeal, we review his arguments only for plain error. See United 

States v. Moriarty, 429 F.3d 1012, 1018 (11th Cir. 2005) (when not raised in the 

district court, both constitutional objections to a plea and objections based on Fed. 

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R. Crim. P. 11 are subject to plain error review). Under the plain-error standard, 

the defendant must show “(1) error, (2) that is plain, and (3) that affects substantial 

rights.” Id. at 1019. An error is “plain” if it is “clear” or “obvious.” United States

v. Gonzalez, 834 F.3d 1206, 1218 (11th Cir. 2016). To show that a plain error 

affected substantial rights in the context of a guilty plea, a defendant “must show a 

reasonable probability that, but for the error, he would not have entered the plea.” 

See United States v. Dominguez Benitez, 542 U.S. 74, 83 (2004). 

“The foundational principles governing guilty plea procedures derive from 

constitutional notions of due process.” United States v. Presendieu, 880 F.3d 1228, 

1238 (11th Cir. 2018). “Because a guilty plea involves the relinquishment of 

several constitutional rights and privileges, it must be entered voluntarily and 

knowingly.” Id. 

Rule 11 “is designed to assist the district court in making the constitutionally 

required determination that a defendant’s guilty plea is truly voluntary.” McCarthy 

v. United States, 394 U.S. 459, 465 (1969). Rule 11 directs specifically that the 

court inform the defendant of -- and make sure the defendant understands -- certain 

matters. See Fed. R. Crim. P. 11(b)(1). In determining whether a defendant’s plea 

is knowing and voluntary, the district court must address three “core concerns” 

underlying Rule 11: (1) whether the plea is free from coercion; (2) whether the 

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defendant understands the nature of the charges; and (3) whether the defendant

understands the consequences of the guilty plea. Presendieu, 880 F.3d at 1238. 

We will uphold a plea colloquy -- even if the district court fails to address 

expressly an item listed in Rule 11 -- when the colloquy addresses adequately the 

three core concerns. See United States v. Hernandez-Fraire, 208 F.3d 945, 950 

(11th Cir. 2000). 

Section 1425(a) makes it a crime to “knowingly procure[] or attempt[] to 

procure, contrary to law, the naturalization of any person, or documentary or other 

evidence of naturalization or of citizenship.” See 18 U.S.C. § 1425(a). To obtain a 

conviction under section 1425(a), the government must prove “that an illegal act 

by the defendant played some role in [his] acquisition of citizenship.” Maslenjak 

v. United States, 137 S. Ct. 1918, 1923 (2017). When -- as in this case -- the 

illegal act is making a false statement, the government must show “that the 

defendant lied about facts that would have mattered to an immigration official, 

because they would have justified denying naturalization or would predictably 

have led to other facts warranting that result.” See id. 

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A.

Izquierdo first complains that the district court failed to explain adequately 

the elements of the charged offense, including specifically the materiality element 

recognized in Maslenjak. We disagree. 

There exists “no rigid formula or ‘mechanical rule’ for determining whether 

the district court adequately informed the defendant of the nature of the charges.” 

Presendieu, 880 F.3d at 1238. Nor does Rule 11 mandate that the district court list 

the elements of the offense. See id.; Fed. R. Crim. P. 11(b)(1)(G). Instead, we 

consider the adequacy of a plea colloquy on a case-by-case basis, “depending on 

the complexity of the charges and the defendant’s intelligence and sophistication.” 

Presendieu, 880 F.3d at 1238. 

At the plea colloquy, the district court discussed with Izquierdo the offense 

charged in the indictment and the terms of the written plea agreement. Izquierdo 

told the district court that he had reviewed and discussed those documents with his

lawyer, understood the nature of the charge against him, and had no unanswered 

questions. The government then recited the factual proffer, which included this 

language: 

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If the defendant had told the truth and informed immigration 

authorities that he was committing the aforementioned offenses, the 

United States Citizenship and Immigration Service, USCIS, would 

have conducted further investigation regarding the defendant’s moral 

character and eligibility for naturalization. By giving false testimony 

to immigration officials about an issue that was material to his 

application, the defendant procured his naturalization contrary to law. 

(emphasis added). 

Izquierdo said he understood the government’s proffer and agreed that he in 

fact had engaged in the conduct described by the government. 

This case involves a single straightforward offense. And nothing evidenced 

that Izquierdo -- who had a master’s degree in veterinarian medicine -- lacked the 

intelligence or sophistication necessary to understand the nature of that charge. 

Given the record, the district court made no clear or obvious error in concluding 

that Izquierdo understood the nature of the charge against him. 

B.

Izquierdo also complains that the district court failed to ensure that he 

understood the consequences of his guilty plea. Izquierdo says the district court 

never explained adequately that a guilty plea would result in mandatory revocation 

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of his United States citizenship and cancellation of his Certificate of 

Naturalization.

Although the district court first said Izquierdo would “likely” lose his 

citizenship, the district court later said expressly -- and Izquierdo agreed -- that 8 

U.S.C. § 1451(e) makes denaturalization a mandatory consequence of pleading 

guilty to a violation of 18 U.S.C. § 1425(a). In addition, both the written plea 

agreement and the Presentence Investigation Report provided that Izquierdo 

“understands that denaturalization is a consequence of pleading guilty” and “that 

pleading guilty may also have other consequences with respect to his immigration 

status.” According to the written plea agreement, Izquierdo also “affirm[ed] that 

he wants to plead guilty regardless of any immigration consequences that his plea 

may entail, even if the consequence is his automatic removal from the United 

States.” 

Given the record in this case, we conclude that the district court addressed 

adequately Rule 11’s “core concerns.” In addition, Izquierdo has failed to allege 

that a reasonable probability exists that -- but for the district court’s alleged Rule 

11 errors -- he would not have entered his guilty plea. Izquierdo, thus, cannot 

show that the alleged errors affected his substantial rights. See Dominguez 

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Benitez, 542 U.S. at 83. The district court committed no plain error in determining 

that Izquierdo’s guilty plea was knowing and voluntary. 

II.

On appeal, Izquierdo now seeks to challenge Question 22 on the 

Application. First, he contends the terms “crime” and “offense” as used on the 

Application are so broad that they render Question 22 unconstitutionally vague. 

Izquierdo next contends that Question 22 required him to incriminate himself in 

violation of the “exculpatory no” doctrine. We reject these arguments.

The void-for-vagueness doctrine applies plainly only to certain statutes; the 

doctrine is thus not clearly applicable to challenge a question on an immigration 

form. See Beckles v. United States, 137 S. Ct. 886, 892-95 (concluding that the 

advisory sentencing guidelines are not subject to a vagueness challenge: the voidfor-vagueness doctrine applies only to “laws that define criminal offenses and laws 

that fix the permissible sentences for criminal offenses.” (emphasis omitted)); 

United States v. Matchett, 837 F.3d 1118, 1122 (11th Cir. 2016) (“the vagueness 

doctrine applies only to laws that regulate private conduct” including laws that 

define crimes, fix sentences, restrict speech, and regulate businesses). About 

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Izquierdo’s second argument, the “exculpatory no” doctrine was eliminated by the 

Supreme Court in Brogan v. United States, 522 U.S. 398, 404 (1998). 

AFFIRMED.

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