Henriquez v. Sessions, 890 F.3d 70 (2d Cir. 2018): Analyzing NY Drug Possession and Bail Jumping Under Immigration Law


Introduction: Henriquez v. Sessions, 890 F.3d 70 (2d Cir. 2018)

On May 8, 2018, the United States Court of Appeals for the Second Circuit published an interesting precedent decision in Henriquez v. Sessions, 890 F.3d 70 (2d Cir. 2018) [PDF version]. Judge José A. Cabranes, writing for a three-judge panel, held that a conviction for fifth degree possession of a controlled substance in violation of New York Penal Law (NYPL) 220.06 for possession of cocaine rendered him removable under section 237(a)(2)(B)(i) of the Immigration and Nationality Act (INA). In so doing, the Second Circuit concluded that NYPL 220.06 was a divisible statute with respect to the substance possessed, which distinguished the matter from the Second Circuit's prior decision in NYPL 220.31 in Harbin v. Sessions, 860 F.3d 58 (2d Cir. 2017) [PDF version]. Finally, the panel held that the petitioner's conviction for bail jumping under NYPL 215.57 was an aggravated felony under section 101(a)(43)(T) of the INA.

In this article, we will discuss the factual and procedural history of Henriquez, the Second Circuit's reasoning and decision, and what the precedent will mean going forward. To learn more about analyzing New York's controlled substances statutes for immigration purposes, please see our companion article on the Second Circuit's 2017 Harbin decision [see article].

Factual and Procedural History

The petitioner, Manuel De Jesus Perez Henriquez (“Perez”), had two criminal convictions in New York which caused him problems in immigration proceedings. He was charged as being removable under section 237(a)(2)(B)(i) (“Any alien who at any time after admission has been convicted of a violation of (or a conspiracy to violate) any law, or regulation of a State, the United States, or a foreign country relating to a controlled substance (as defined in [21 U.S.C. 802]), other than a single offense involving possession for one's own use of 30 grams or less of marijuana, is deportable”) as a result of his conviction for violating NYPL 220.06 (possession of a controlled substance in the fifth degree).

Perez challenged the underlying charge, but in the alternative, sought relief in the form of cancellation of removal for non-lawful permanent residents. However, the immigration judge found that Perez was removal as charged and found that he was ineligible for cancellation of removal because his separate conviction for bail jumping under NYPL 215.57 was an aggravated felony under section 101(a)(43)(T) of the INA (defines as an aggravated felony “an offense relating to a failure to appear before a court pursuant to a court order to answer to or dispose of a charge of a felony for which a sentence of 2 years' imprisonment or more may be imposed”).

The Board of Immigration Appeals (BIA) affirmed the decision of the immigration judge and denied Perez's petition for review. Perez challenged the Board's determinations that he was removable for a controlled substances offense and that his conviction for bail jumping was an aggravated felony on appeal to the Second Circuit.

Discussion of Perez's Drug Conviction

The Second Circuit explained that possession of a controlled substance in the fifth degree under NYPL 220.06 is not categorically a controlled substance offense. This is because, as the Second Circuit noted in Harbin v. Sessions, 860 F.3d 58, 63 (2d Cir. 2017) [see article], the New York controlled substance schedules contain at least one substance that is not included in the federal schedules. This is significant in the immigration context because section 237(a)(2)(B)(i) incorporates the federal schedules.

However, while in Harbin the Second Circuit held that NYPL 220.31 was not an immigration offense because it was not divisible with regard to the specific substance which led to the conviction, the Court found in the instant case that NYPL 220.06 “is a divisible statute, because each distinct subsection of the statute contains separate elements that much be proven beyond a reasonable doubt in order to sustain a conviction under that subsection.” In Mathis v. United States, 136 S.Ct. 2243, 2249 (2016) [see article], the Supreme Court of the United States held that a statute is divisible when it lists elements in the alternative. Here, it is important to note that an element is a part of the statute that must be proven in order to sustain a conviction.

A statute is not divisible if it merely lists different means of committing an offense whereby the specific mode of commission does not need to be established in order to sustain a conviction. For example, if the specific drug involved in a drug offense must be proven beyond a reasonable doubt (e.g., the jury must agree that the drug was cocaine and not any other banned substance), the statute is divisible, whereas if it only needs to be proven that any controlled substance on the list of controlled substances was involved, the statute is not divisible.

Because the Second Circuit found that NYPL 220.06 was divisible, it concluded that the immigration judge and the BIA properly followed the Supreme Court decision in Shepard v. United States, 544 U.S. 13 (2005) [PDF version] in looking at documents underlying the conviction to determine under which subsection of the statute Perez was convicted (in this case, the specific substance he was convicted of possessing).

Perez argued that, even if the Second Circuit were to conclude that NYPL 220.06 was not divisible, the government had still failed to sustain its burden that he was convicted of possessing a substance that is included on the federal controlled substance schedules. To assess this argument, the Second Circuit examined the evidence. In order to establish that Perez's conviction involved a federally controlled substance rather than a substance that is criminalized by New York but not included in the federal schedule, the government submitted the following three “Shepard documents”: ” (1) a superior court information, a (2) waiver of indictment, and (3) a certificate of disposition.” The government used these documents to attempt to establish that Perez had pled guilty to violating subsection 5 of NYPL 220.06, which specifically criminalizes the possession of cocaine that weights 500 milligrams or more.

The Second Circuit found that “The information [in the Shepard documents] makes clear that Perez was charged with violating NYPL 220.06 subsection (5), and it also specifically mentions cocaine.” However, Perez's waiver of indictment did not specify which controlled substance he possessed in the fifth degree. Furthermore, the final certificate of disposition stated only that Perez pled guilty to “criminal possession of a controlled substance 5th degree PL 220.06.”

Ultimately, the Second Circuit agreed with the government's position that the documents offered and the evidence in the record established that Perez pled guilty to violation NYPL 220.06(5) for possession of cocaine. The Second Circuit noted that “the government could have provided a more complete record of conviction,” but it found it significant that Perez did “not argue in his briefing that he could have pleaded guilty to a different subsection of [NYPL] 220.06 than that listed on the information.” As a result, the Second Circuit wrote that Perez “thus appears to concede that he could not have pleaded guilty to a different subsection than that charged in the information, while simultaneous arguing that the government has not offered sufficient proof that he pleaded to guilty to that subsection.”

Because cocaine is a controlled substance under federal law, the Board held that the BIA was correct in concluding that Perez had been convicted of a controlled substance offense under the INA.

Discussion of Perez's Bail Jumping Conviction

Having established that Perez was correctly found to be removable for a drug offense, the Board moved on to address the question about whether Perez's conviction for bail jumping was an aggravated felony under section 101(a)(43)(T). The Board evaluated the issue under Chevron USA Inc. v. Natural Resources Defense Council, Inc., 467 U.S. 837 (1984) [PDF version], wherein the Supreme Court established parameters for when to defer to an agency's interpretation of a statute, namely, when (1) the statute is ambiguous, and (2) when the agency's interpretation of the ambiguous statute is reasonable. The Second Circuit would ultimately defer to the BIA's interpretation, which was set forth in Matter of Garza-Olivares, 26 I&N Dec. 736, 739 (BIA 2016) [see article].

First, the following is the language of NYPL 215.57 — Bail jumping in the first degree:

A person is guilty of bail jumping in the first degree when by court order he has been released from custody or allowed to remain at liberty, either upon bail or upon his own recognizance, upon condition that he will subsequently appear personally in connection with an indictment pending against him which charges him with the commission of a class A or class B felony, and when he does not appear personally on the required date or voluntarily within thirty days thereafter.

Bail jumping in the first degree is a class D felony.

First, the Board held that it must consider whether NYPL 215.57, the respondent's statute of conviction, satisfied the elements of section 101(a)(43)(T), “which requires (1) a 'failure to appear' (2) 'before a court' (3) 'pursuant to a court order' (4) 'to answer to or dispose of a charge of a felony' (5) 'for which a sentence of 2 years' imprisonment or more may be imposed.'” The Second Circuit found that NYPL 215.57 satisfied elements (1) thru (4) on its face, leaving the fifth element as the only open question.

The issue in the instant case was whether the “for which a sentence of 2 years' imprisonment or more may be imposed” relates to the sentence for the crime of bail jumping or to the sentence for the petitioner's underlying felony. The Second Circuit agreed with the government that it relates to the petitioner's commission of bail jumping. Here, the Second Circuit found the language of the aggravated felony provision at section 101(a)(43)(Q) — which specifies that the “underlying offense [must be] publishable by a term of 5 years or more,” from section 101(a)(43)(T). It referenced its published decision In re Barnet, 737 F.3d 238, 247 (2d Cir. 2013) [PDF version], wherein it wrote that “Statutory enactments should … be read so as to give effect, if possible, to every clause and word of a statute.”

The Second Circuit then considered “whether section [101(a)(43)(T)'s] phrase 'may be imposed' refers to a sentence for which the maximum penalty is more than two years or for which the minimum sentence must exceed two years.” Based on the language employed by and interpretations of other aggravated felony provisions, the Second Circuit joined the United States Court of Appeals for the Ninth Circuit (Renteria-Morales v. Mukasey, 551 F.3d 1076, 1089 (9th Cir. 2008) [PDF version], and Third Circuit (United States v. Graham, 169 F.3d 787, 791 (3d Cir. 1999) [PDF version]), in holding that “'may be imposed' refers to the maximum penalty authorized.” The Board had reached the same conclusion in Matter of Garza-Olivares.

Because the maximum penalty for bail jumping under NYPL 215.57 was seven years' imprisonment (see NYPL 70.00(2)(d)), the Second Circuit concluded that it fulfilled the length-of-sentence requirement in section 101(a)(43)(T) of the INA.

For this reason, the Second Circuit found that the Board did not err in concluding that Perez's bail jumping conviction was an aggravated felony which rendered him ineligible for cancellation of removal.


Henriquez v. Sessions is interesting on two counts. First, it shows the limits of the Second Circuit's decision in Harbin [see article]. While the Second Circuit noted in Harbin that New York's drug schedules are categorically overbroad with respect to the federal drug schedules, Henriquez makes clear that New York drug statutes that are divisible with regard to the substance involved may still constitute immigration offenses. Second, the Second Circuit followed the Board's reading of section 101(a)(43)(T) as precedent, while also providing specific discussion about NYPL 215.57.

Any alien charged with removability should consult with an experienced immigration attorney immediately for case-specific guidance. Henriquez highlights the fact that drug convictions and aggravated felony convictions carry serious — and often fatal — consequences in the immigration context.

To learn more about some of the issues discussed in this article, please see our website's growing categories on criminal aliens [see category] and removal and deportation defense [see category].