United States v. Castillo

21-527
United States v. Castillo

In the
United States Court of Appeals
For the Second Circuit

August Term, 2021
No. 21-527

UNITED STATES OF AMERICA,
Appellee,

v.

CHAYANNE CASTILLO, AKA BAMBI,
Defendant-Appellant.

On Appeal from a Judgment of the United States District Court for
the Southern District of New York.

ARGUED: MARCH 9, 2022
DECIDED: JUNE 8, 2022

Before: SACK, LOHIER, and NARDINI, Circuit Judges.

Defendant-Appellant Chayanne Castillo was sentenced to a 40-
month term of imprisonment for being a felon in possession of a
firearm, in violation of 18 U.S.C. § 922(g)(1). In calculating Castillo’s
advisory sentencing range under the United States Sentencing
Guidelines, the United States District Court for the Southern District
of New York (Cathy Seibel, Judge) concluded that Castillo’s prior
conviction for attempted second-degree gang assault in violation of
New York Penal Law §§ 120.06 and 110.00 was a qualifying “crime of
violence” for which his base offense level would be raised from 14 to
20. On appeal, Castillo argues that his conviction is not a crime of
violence under the categorical approach because New York courts
have deemed attempted second-degree gang assault a legal
impossibility. We agree, and therefore VACATE Castillo’s sentence
and REMAND for resentencing.

SHIVA H. LOGARAJAH (Karl Metzner, on the
brief), Assistant United States Attorneys, for
Damian Williams, United States Attorney
for the Southern District of New York, New
York, NY, for Appellee.

DANIEL HABIB, Federal Defenders of New
York, Inc., New York, NY, for Defendant-
Appellant.

WILLIAM J. NARDINI, Circuit Judge:

In this appeal, we must answer a now-familiar question: Does

a criminal defendant’s prior conviction qualify as a “crime of

violence” and thus subject him to a higher sentence for a subsequent

federal conviction? In Defendant-Appellant Chayanne Castillo’s

2
case, however, the answer depends on two peculiarities of New York

law. First, New York allows criminal defendants to plead guilty to

legally impossible offenses. Castillo did just that. Second, the legally

impossible offense to which Castillo pled guilty—namely, attempted

second-degree gang assault in violation of New York Penal Law

§§ 120.06 and 110.00—involves the incoherent premise that the

defendant intended to cause an unintended result. The United States

District Court for the Southern District of New York (Cathy Seibel,

Judge) determined that attempted second-degree gang assault was a

crime of violence sufficient to raise Castillo’s base offense level under

the United States Sentencing Guidelines. We conclude, however, that

Castillo’s conviction for this particular offense did not include an

element constituting the use, attempted use, or threatened use of

physical force, and so it should not have been used to enhance his

Guidelines range. We therefore VACATE Castillo’s sentence and

REMAND for resentencing.

3
I. Background

On June 26, 2020, Castillo was charged in a one-count

indictment with being a felon in possession of a firearm in violation

of 18 U.S.C. § 922(g)(1). Castillo pleaded guilty to this charge without

a plea agreement on November 19, 2020.

In its Presentence Report, the United States Probation Office

(“Probation”) applied U.S.S.G. § 2K2.1(a)(4)(A). That section

provides for a base offense level of 20 for the unlawful possession of

a firearm if “the defendant committed any part of the instant offense

subsequent to sustaining one felony conviction of either a crime of

violence or a controlled substance offense.” The application notes to

§ 2K2.1 dictate that the phrase “‘[c]rime of violence’ has the meaning

given that term in § 4B1.2(a) and Application Note 1 of the

Commentary to § 4B1.2.” U.S.S.G. § 2K2.1, comment. (n.1). In turn,

§ 4B1.2, also known as the Career Offender Guideline, defines “crime

of violence” to mean “any offense under federal or state law,

punishable by imprisonment for a term exceeding one year, that—

4
(1) has as an element the use, attempted use, or threatened use of

physical force against the person of another,” or (2) is one of a series

of enumerated crimes including “aggravated assault.” U.S.S.G.

§ 4B1.2(a)(1)–(2). Subsections (1) and (2) are known as the “force

clause” and the “enumerated offenses clause,” respectively.

Application Note 1 of the Commentary to § 4B1.2 further states that

the term “crime of violence . . . include[s] the offenses of aiding and

abetting, conspiring, and attempting to commit such offenses.”

U.S.S.G. § 4B1.2, comment. (n.1).

Probation determined that Castillo had a felony conviction for

a crime of violence: a 2011 conviction for attempted second-degree

gang assault in violation of New York Penal Law §§ 120.06 and 110.00.

“A person is guilty of gang assault in the second degree when, with

intent to cause physical injury to another person and when aided by

two or more other persons actually present, he causes serious physical

injury to such person or to a third person.” N.Y. Penal Law § 120.06.

5
New York law defines “[p]hysical injury” as “impairment of physical

condition or substantial pain,” id. § 10.00(9) (internal quotation marks

omitted), and “[s]erious physical injury” as “physical injury which

creates a substantial risk of death, or which causes death or serious

and protracted disfigurement, protracted impairment of health or

protracted loss or impairment of the function of any bodily organ,”

id. § 10.00(10) (internal quotation marks omitted). New York law

provides that a person “is guilty of an attempt to commit a crime

when, with intent to commit a crime, he engages in conduct which

tends to effect the commission of such crime.” Id. § 110.00.

Without the enhancement for a prior crime of violence,

Castillo’s base offense level would have been 14. See U.S.S.G.

§ 2K2.1(a)(6)(A). Instead, after subtracting three levels for acceptance

of responsibility, Probation arrived at a total offense level of 17. In

combination with his criminal history category of V, this base offense

6
level yielded an advisory Guidelines range of 46 to 57 months of

imprisonment.

Castillo objected to the use of his prior conviction to increase

his base offense level, arguing that attempted second-degree gang

assault is not a crime of violence for three reasons: (1) second-degree

gang assault requires only intent to cause physical injury, not serious

physical injury, and so the offense does not meet the minimum level

of violent force required; (2) second-degree gang assault could be

committed by omission and thus does not categorically require the

“use” of force; and (3) second-degree gang assault is not generic

“aggravated assault” as enumerated in § 4B1.2(a)(2).

Castillo was sentenced on March 3, 2021. The district court

overruled Castillo’s objection to the use of his prior conviction to

enhance his base offense level. It rejected Castillo’s first argument,

finding that “a knowing and intentional causing of physical injury . . .

necessarily involves physical force,” and that “[t]he requirement that

7
two or more people be[] in the immediate vicinity aiding the actor

made it obvious that the statute requires use of violent force.” App’x

at 64, 66. Relying on our en banc decision in United States v. Scott, 990

F.3d 94 (2d Cir. 2021), in which we held that even an offense that can

be committed by omission can involve the use of force, id. at 125, the

district court also rejected Castillo’s second argument. Because the

district court found that attempted second-degree gang assault was a

crime of violence under U.S.S.G. § 4B1.2(a)’s force clause, it did not

reach his third argument, that his prior conviction was not generic

“aggravated assault” under § 4B1.2(a)’s enumerated offenses clause.

Ultimately, the district court agreed with Probation’s

calculation of Castillo’s base offense level at 20, resulting in a total

offense level of 17 after adjustment for Castillo’s acceptance of

responsibility. After accounting for Castillo’s criminal history

category of V, the district court arrived at an advisory Guidelines

range of 46 to 57 months. After considering the factors outlined in 18

8
U.S.C. § 3553(a), the district court decided to “go a little bit below the

guidelines, but . . . not . . . a lot below the guidelines.” App’x at 81–

82. The district court sentenced Castillo to a 40-month term of

imprisonment. This appeal followed.

II. Discussion

“We review a sentence on appeal for procedural and

substantive reasonableness.” United States v. Seabrook, 968 F.3d 224,

232 (2d Cir. 2020). “A district court commits procedural error when

. . . it makes a mistake in its Guidelines calculation.” Id. Whether an

offense is a “crime of violence” under the Career Offender Guideline

is a question of law that we decide de novo. Scott, 990 F.3d at 104.

On appeal, Castillo argues that the district court erred by

classifying attempted second-degree gang assault as a crime of

violence under U.S.S.G. §§ 2K2.1(a)(4)(A) and 4B1.2(a)(1) and, as a

result, using a base offense level of 20 to calculate his advisory

Guidelines range. He contends in part that his crime of conviction—

attempted second-degree assault—is not a “crime of violence” within

9
the meaning of § 4B1.2(a)’s force clause because it is legally impossible

under New York law, does not entail a coherent mens rea, and

therefore cannot be said to categorically constitute a crime of

violence. 1

A. Legally impossible crimes under New York law

Much of Castillo’s argument depends upon the implications of

his crime of conviction—attempted second-degree gang assault—

being legally impossible. New York law allows a defendant to plead

guilty to a “nonexistent or legally impossible offense in satisfaction of

an indictment that charges a higher offense” to facilitate the plea-

bargaining process and further the policy interests that this process

serves. People v. Tiger, 32 N.Y.3d 91, 101 (2018). In approving this

1 The Government contends that Castillo failed to preserve this argument.
Because Castillo argued in the district court that the intent element of second-
degree gang assault does not sufficiently align with the definition of “crime of
violence” found in U.S.S.G. § 4B1.2 and because the legal impossibility argument
likewise focuses on the inadequacy of the intent element of his crime of conviction,
we deem his argument sufficiently preserved for appellate review. See Eastman
Kodak Co. v. STWB, Inc., 452 F.3d 215, 221 (2d Cir. 2006) (explaining that this Court
“may entertain additional support that a party provides for a proposition
presented below”).

10
unusual practice, the New York Court of Appeals has emphasized

that a defendant who knowingly accepts a plea to a legally impossible

offense “in satisfaction of an indictment charging a crime carrying a

heavier penalty” has “declined to risk his chances with a jury” and

received the “substantial benefit” of a decreased sentencing range.

People v. Foster, 19 N.Y.2d 150, 153 (1967). Put differently, a plea to a

legally impossible offense “should be sustained on the ground that it

was sought by [the] defendant and freely taken as part of a bargain

which was struck for the defendant’s benefit.” Id. at 154.

Under New York law, an attempt “consists of an intent to bring

about the result which the particular law proscribes and, in addition,

an act in furtherance of that intent.” People v. Campbell, 72 N.Y.2d 602,

605 (1988); see also N.Y. Penal Law § 110.00 (“A person is guilty of an

attempt to commit a crime when, with intent to commit a crime, he

engages in conduct which tends to effect the commission of such

crime.”). “[W]here a penal statute imposes strict liability for creating

11
an unintended result, an attempt to commit that crime is not a legally

cognizable offense” because “[o]ne cannot attempt to create an

unintended result.” People v. Prescott, 95 N.Y.2d 655, 659 (2001).

Although the New York Court of Appeals has not had occasion to

apply this general rule to the specific conviction at issue in this case,

the Appellate Division has twice done so. The First Department has

held that attempted second-degree gang assault is a “legal

impossibility” because it criminalizes the attempt to cause an

unintended result. People v. Delacruz, 110 N.Y.S.3d 682, 683 (1st Dep’t

2019) (internal quotation marks omitted); In re Cisely G., 918 N.Y.S.2d

23, 24 (1st Dep’t 2011).

B. Applying the categorical approach to Castillo’s
conviction

1. The force clause

The district court determined that Castillo’s prior conviction

was a crime of violence under § 4B1.2(a)’s force clause. To evaluate

whether a crime “has as an element the use, attempted use, or

12
threatened use of physical force against the person of another,”

U.S.S.G. § 4B1.2(a)(1), courts use the categorical approach, see United

States v. Moore, 916 F.3d 231, 240 (2d Cir. 2019); see also Taylor v. United

States, 495 U.S. 575, 600 (1990). A court must identify the elements of

the offense, “determine the minimum criminal conduct necessary to

satisfy th[ose] elements . . . without regard to whether the defendant

himself engaged in more egregious conduct,” and then “decide

whether a necessary component of that minimum conduct is the

defendant’s use of physical force.” Scott, 990 F.3d at 104–05. Where

a state law crime is at issue, “[w]e look to state law in identifying the

elements of [the] crime, but to federal law in determining whether the

consequences of the conduct that those elements require render

conviction for that conduct a violent crime under federal law.” Id. at

104 (cleaned up). Because the Career Offender Guideline’s force

clause, set forth at § 4B1.2(a)(1), is identical to the force clause found

in the Armed Career Criminal Act, 18 U.S.C. § 924(e)(2)(B) (“ACCA”),

13
we may draw upon case law interpreting ACCA’s force clause to help

us interpret U.S.S.G. § 4B1.2(a)(1). Scott, 990 F.3d at 104.

Castillo argues that the district court erred by classifying his

prior conviction as a “crime of violence” within the meaning of

U.S.S.G. § 4B1.2(a)’s force clause. He asserts that, because attempted

second-degree assault is a legally impossible crime with incoherent

elements, it cannot be evaluated under the categorical approach,

which focuses solely on the elements of a crime and whether they

include the use, attempted use, or threatened use of physical force.

We have repeatedly emphasized that the categorical approach

requires an evaluation of the elements of a crime to determine if the

defendant’s use of physical force is among them. See Scott, 990 F.3d

at 104–05 (describing the categorical approach as an “inquiry to

determine the minimum criminal conduct necessary to satisfy the

elements of a crime” and whether that minimum conduct involves

“the defendant’s use of physical force”); Gray v. United States, 980 F.3d

14
264, 265–66 (2d Cir. 2020) (“Under the categorical approach, we

compare the elements of the offense . . . to the statutory definition of

‘crime of violence,’ . . . without regard to the particular facts of the

defendant’s offense conduct.”); Hill, 890 F.3d at 55 (“[C]ourts look

only to the statutory definitions—i.e., the elements—of the offense,

and not to the particular underlying facts.” (alterations and internal

quotation marks omitted)).

What, then, are the elements of attempted second-degree gang

assault under New York law? As an initial matter, Castillo argues

that the elements of a legally impossible crime are “nonexistent.”

Castillo Br. at 23. In pressing this argument, Castillo relies on People

v. Martinez, in which the defendant was indicted and tried for, but

ultimately acquitted of, attempted murder in the second degree.

People v. Martinez, 81 N.Y.2d 810, 811 (1993). However, the trial court

instructed the jury on attempted manslaughter in the first degree as a

lesser included offense. See id. Like second-degree gang assault, first-

15
degree manslaughter is defined, in part, by the unintentional

causation of bodily harm, specifically death. N.Y. Penal Law

§ 125.20(1). The jury returned a verdict convicting the defendant of

attempted first degree manslaughter, but the New York Court of

Appeals vacated the conviction because “[i]t is settled law that

attempted manslaughter in the first degree . . . is a nonexistent crime.”

Martinez, 81 N.Y.2d at 811. The Court of Appeals held that “[s]ince

the crime does not exist in the Penal Law, there could not be evidence

to support such a conviction beyond a reasonable doubt” at trial. Id.

at 812. However, we do not read Martinez to mean that a legally

impossible crime can never have any discernable elements. In fact,

the New York Court of Appeals’s reasoning implies otherwise. The

Court of Appeals reasoned that, “[f]or a conviction, a jury must find

the defendant guilty of each element of the crime beyond a reasonable

doubt, but could not do so here because an element of attempted

manslaughter in the first degree as charged is an unintended result that as

16
a matter of law cannot be attempted.” Id. (emphasis added). In other

words, Martinez held that first-degree manslaughter was a legally

impossible offense because one particular element—intending an

unintended result—would be incoherent.

Instead, we think the proper mode of analysis is to parse the

elements of Castillo’s conviction and determine whether each is (1)

coherent; and, if so, (2) constitutes the use, attempted use, or

threatened use of physical force. As discussed earlier, “[a] person is

guilty of gang assault in the second degree when, with intent to cause

physical injury to another person and when aided by two or more

other persons actually present, he causes serious physical injury to

such person or to a third person.” N.Y. Penal Law § 120.06. The three

elements of completed second-degree gang assault are readily

identified by the text of N.Y. Penal Law § 120.06. The first element

identifies the mens rea—“intent to cause physical injury.” Id. The

second element establishes the “gang” aspect of gang assault—the

17
defendant must be “aided by two or more other persons actually

present.” Id. The third element identifies the actus reus—the

causation of “serious physical injury.” Id. Because Castillo was

convicted not of completed second-degree gang assault, but of

attempted second-degree gang assault, we must analyze these

elements through the lens of New York’s criminal attempt statute,

which provides that “[a] person is guilty of an attempt to commit a

crime when, with intent to commit a crime, he engages in conduct

which tends to effect the commission of such crime.” Id. § 110.00.

That is, the mens rea of attempt is the “intent to commit [the object]

crime,” N.Y. Penal Law § 110.00, which requires that the defendant

“specifically intend[] all elements of th[e object] offense,” Gill v. I.N.S.,

420 F.3d 82, 90 (2d Cir. 2005). The actus reus of attempt is the

“engag[ing] in conduct which tends to effect the commission of [the

object] crime,” N.Y. Penal Law § 110.00, which requires that the

defendant “engage[] in conduct that came ‘dangerously near’

18
commission of the completed crime,” People v. Kassebaum, 95 N.Y.2d

611, 618 (2001).

The requirements of the New York attempt statute can be

intelligibly read in tandem with the mens rea element of second-

degree gang assault—the specific intent to cause physical injury. Cf.

People v. McDavis, 469 N.Y.S.2d 508, 510 (4th Dep’t 1983) (“[T]here can

be no attempt to commit a crime that does not involve a specific

intent, such as . . . a crime predicated upon a reckless act.”). In this

way, Castillo’s conviction is different from the conviction at issue in

Gill v. I.N.S. In Gill, we concluded that a guilty plea to attempted

reckless assault in violation of N.Y. Penal Law § 120.05(4) was not a

crime involving moral turpitude capable of rendering the petitioner,

a lawful permanent resident, removable under the immigration laws.

Gill, 420 F.3d at 88, 91. In so holding, we relied, in part, on the

incompatibility between the specific intent required to commit an

attempt under New York law and the mens rea of the petitioner’s

19
object offense, recklessness. See id. at 90–91. Noting that “[i]t is in the

intent that moral turpitude inheres,” id. at 89 (internal quotation

marks omitted), and “[w]ithout in any way questioning the state’s

ability to hold a defendant to his plea to an attempted reckless crime,”

we held that “no mental state can be clearly discerned from such a

conviction, let alone the sort of aggravated recklessness that has been

found to demonstrate moral turpitude,” id. at 91. Unlike the reckless

assault at issue in Gill, however, Castillo’s crime of conviction

requires a mens rea of specific intent to cause physical injury. No

incompatibility arises between the specific intent required to commit

an attempt and the mens rea required to commit second-degree gang

assault. Thus, Castillo’s guilty plea to attempted second-degree gang

assault coherently reflects Castillo’s specific intent to cause physical

injury.

That conclusion, however, does not end our larger inquiry.

Even assuming that the causation of “physical injury” as defined by

20
New York law would involve the quantum of “violent force”

sufficient to constitute the use of “physical force” under the

categorical approach, 2 see Scott, 990 F.3d at 105, the mere intent to use

physical force, without more, does not constitute “the use, attempted

use, or threatened use of physical force against the person of another,”

U.S.S.G. § 4B1.2(a)(1) (emphases added).

Turning to the second element of second-degree gang assault—

that the defendant be aided by two or more people actually present—

we likewise see no incompatibility between that element and the

requirements of New York’s attempt statute. The New York Court of

Appeals has explained that this element requires that the others must

“simply be present and render aid to the defendant,” but need not

“share [the] defendant’s intent to cause physical injury.” People v.

2 We need not determine whether the causation of “physical injury” as
defined by New York law involves enough force to constitute the use of “‘physical
force’ . . . [which] means ‘violent force,’ i.e., ‘force capable of causing physical pain
or injury to another person,’” Scott, 990 F.3d at 105 (quoting Johnson v. United States,
559 U.S. 133, 140 (2010)), in order to resolve Castillo’s appeal. Accordingly, we
express no opinion on the matter.

21
Sanchez, 13 N.Y.3d 554, 565 (2009). A defendant could conceivably

intend that two or more people be present and aid him during an

assault, and so no conceptual incoherence arises when considering

this element of second-degree gang assault through the lens of the

attempt statute.

But an intent to have the presence and aid of others does not

categorically involve the use, attempted use, or threatened use of

physical force. In arguing otherwise, the government analogizes to

our decision in United States v. Pereira-Gomez, 903 F.3d 155 (2d Cir.

2018), in which we held that attempted second-degree robbery in

violation of N.Y. Penal Law §§ 110.00 and 160.10 was a crime of

violence under the force clause under Application Note 1(B)(iii) to the

version of U.S.S.G. § 2L1.2 found in the 2014 version of the Guidelines.

Id. at 165–66. We did so because “New York defines robbery as

‘forcible stealing,’ which requires ‘us[ing] or threaten[ing] the

immediate use of physical force upon another person.’” Id. at 165

22
(quoting N.Y. Penal Law § 160.00). Because the “level of physical

force must be enough ‘to prevent resistance to the taking or to compel

the owner to deliver up the property,’” we concluded that “[b]y its

plain language, . . . New York’s robbery statute includes as an element

the use of violent force.” Id. (quoting People v. Jurgins, 26 N.Y.3d 607,

614 (2015)). The defendant in Pereira-Gomez argued that several

decisions of the New York Appellate Division established that

robbery does not necessarily involve the use of violent force and

pointed to a decision “in which defendants were convicted of robbery

by forming a human wall that blocked the victim’s path, and another

in which the defendant physically blocked the victim’s passage.” Id.

at 165–66 (internal quotation marks omitted). In rejecting the

defendant’s argument that these particular factual scenarios did not

involve the use, attempted use, or threatened use of physical force,

we held that “[t]he ‘human wall’ was no mere obstacle to the victim’s

pursuit of the robber; it constituted a threat that pursuit would lead

23
to violent confrontation” and “[s]o too did blocking the victim’s

passage in the latter case” because “[o]nly by backing down in the

face of these threats did the victims avoid physical force.” Id. at 166.

However, in so holding, we did not establish a rule that the

intended presence of co-perpetrators categorically amounts to a

threatened use of force. Several decisions by New York courts

interpreting the gang assault statutes 3 and the second-degree robbery

statute, which contains a similarly worded element, see Sanchez, 13

N.Y.3d at 564–65 (“The interpretation of the robbery statute is equally

applicable to the similarly worded gang assault statutes.”),

demonstrate that this element does not categorically involve the use,

attempted use, or threatened use of physical force. For example, a

defendant was “aided by another person actually present” where his

3 In addition to the offense of second-degree gang assault, New York law
criminalizes first-degree gang assault, which is committed “when, with the intent
to cause serious physical injury to another person and when aided by two or more
other persons actually present, [a defendant] causes serious physical injury to such
person or to a third person.” N.Y. Penal Law § 120.07.

24
codefendant pointed out the complainant as a suitable victim and

then, in response to a hand signal from the defendant, the

“codefendant and an unapprehended accomplice took up a position

approximately 10 feet away, ready to render immediate assistance to

[the] defendant if needed.” People v. Stokes, 716 N.Y.S.2d 666, 667 (1st

Dep’t 2000). Likewise, a defendant was aided by two or more persons

actually present in the commission of an assault where “the driver

and the passengers in the backseat of the vehicle that the defendant

was riding in when he shot the complainant” were “in a position to

render immediate assistance to the defendant should it prove

necessary.” People v. Marquez, 751 N.Y.S.2d 251, 253 (2d Dep’t 2002).

As these examples demonstrate, the intended presence and aid of two

or more persons actually present does not categorically involve the

use, attempted use, or threatened use of physical force. 4

4We recognize that New York courts have occasionally characterized this
requirement as “pos[ing] a sufficient threat of additional violence so as to satisfy
the aggravating element necessary to sustain” a conviction for gang assault.

25
 We have concluded that the mens rea element of second-degree

gang assault is compatible with New York’s requirements for

attempt, and that the intended presence of multiple people who are

actually present is also legally coherent, but neither element itself

constitutes the use, attempted use, or threatened use of physical force.

So far, so good. But the legal coherence of Castillo’s sentencing

enhancement breaks down when we apply the requirements of the

attempt statute to the actus reus of second-degree gang assault—the

causation of serious physical injury. “Since second-degree gang

assault involves the intended result of physical injury and the

unintended result of serious physical injury, it . . . cannot be attempted

because ‘there can be no attempt to commit a crime where one of the

Marquez, 751 N.Y.S.2d at 253 (emphasis added). But the Court of Appeals of New
York has also characterized the requirement as “pos[ing] a sufficient risk of
additional violence.” Sanchez, 13 N.Y.3d at 564 (emphasis added). As some district
courts in this Circuit have noted, “[w]hile the mere presence of another person
actually present may increase the risk of injury,” it does not categorically satisfy
the force clause. Laster v. United States, No. 06 CR. 1064, 2016 WL 4094910, at *3
(S.D.N.Y. Aug. 2, 2016) (emphasis added); see also United States v. Pascual, 199 F.
Supp. 3d 670, 678 (N.D.N.Y. 2016).

26
elements is a specific intent but another, an unintended result.’” In re

Cisely G., 918 N.Y.S.2d at 24 (emphasis added) (quoting McDavis, 469

N.Y.S.2d at 510); cf. United States v. Moreno, 821 F.3d 223, 230 (2d Cir.

2016) (“Because it is legally impossible to intend to commit a crime

that is defined . . . by an unintended result, one cannot attempt to

commit reckless second degree assault . . . .”). In this way, Castillo’s

conviction is like the petitioner’s conviction in Gill, 420 F.3d at 91. In

Gill, we noted that “[a] defendant can only be guilty of attempted

assault if he specifically intended all elements of that offense, but

§ 120.05(4) is worded such that a defendant can be convicted simply

because his assault resulted in serious injury, regardless of whether he

intended such a result.” Id. at 90. We held that the offense at issue

could not be a crime involving moral turpitude partly because of the

legal impossibility of attempting an unintended result. Id. at 91. Put

another way, it is legally incoherent to say that a defendant intends to

cause an unintended result. And because this third element of New

27
York attempted second-degree gang assault breaks down into

incoherence, we cannot say that this element necessarily involves the

“use, attempted use, or threatened use of force against the person of

another.” U.S.S.G. § 4B1.2(a)(1).

In sum, although we can successfully discern some information

from Castillo’s conviction for attempted second-degree gang assault,

what we can discern does not satisfy the force clause. We therefore

cannot say, with the level of certainty required by the categorical

approach, that Castillo’s conviction for attempted second-degree

gang assault definitively reflects that he used, attempted to use, or

threatened to use physical force, and it was error for the district court

to conclude otherwise. 5

5 Nor was the error harmless. Here, the use of Castillo’s prior conviction
to apply a crime of violence enhancement increased the applicable Guidelines
range from 27–33 months to 46–57 months. Without the crime-of-violence
enhancement, Castillo’s base offense level would have been 14. U.S.S.G.
§ 2K2.1(a)(6)(A). After a two-level reduction for acceptance of responsibility, see
U.S.S.G. § 3E1.1(a), Castillo’s total offense level would have been 12. After taking
into account his Criminal History Category of V, the resulting sentencing range
would have been 27–33 months. Moreover, the district court explicitly tied its

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 2. The Government’s alternative arguments

The Government offers two alternative arguments upon which

we might rely to affirm the district court’s decision. We conclude that

neither is persuasive.

a. Application Note 1 to U.S.S.G. § 4B1.2

The Government first argues that Castillo’s prior conviction

qualifies as a crime of violence under Application Note 1 to U.S.S.G.

§ 4B1.2. Application Note 1 provides that the phrase “‘[c]rime of

violence’ . . . include[s] the offenses of aiding and abetting, conspiring,

and attempting to commit such offenses.” U.S.S.G. § 4B1.2, comment.

(n.1). The Government argues that “because Gang Assault in the

Second Degree is a crime of violence, Application Note 1 . . . makes

Attempted Gang Assault in the Second Degree a crime of violence as

well.” Gov’t Br. 22. Even assuming that completed second-degree

gang assault is a crime of violence, a conclusion we need not and do

ultimate sentencing decision to the applicable Guidelines range, stating its
intention to “go a little bit below the guidelines, but . . . not . . . a lot below the
guidelines.” App’x at 81–82.

29
not reach today, Castillo’s conviction does not fall within the ambit of

Application Note 1.

We have held that “attempt,” as the word is used in the body

of U.S.S.G. § 4B1.2(a)(1), is “generic attempt.” United States v. Tabb,

949 F.3d 81, 86 (2d Cir. 2020). “Under ‘the normal rule of statutory

interpretation . . . identical words used in different parts of the same

statute are generally presumed to have the same meaning.’” T.W. v.

N.Y. State Bd. of L. Exam’rs, 996 F.3d 87, 99 (2d Cir. 2021) (quoting IBP,

Inc. v. Alvarez, 546 U.S. 21, 34 (2005)). Attempt, as the word is used in

Application Note 1 to U.S.S.G. § 4B1.2, then, also takes its generic

definition. See United States v. Faulkner, 950 F.3d 670, 675 (10th Cir.

2019); United States v. Benítez-Beltrán, 892 F.3d 462, 467–68 (1st Cir.

2018); United States v. Dozier, 848 F.3d 180, 186 (4th Cir. 2017). This is

consistent with the “general rule . . . that unless Congress gives plain

indication to the contrary, federal laws are not to be construed so that

their meaning hinges on state law.” Ming Lam Sui v. I.N.S., 250 F.3d

30
105, 114 (2d Cir. 2001); see also Taylor, 495 U.S. at 590–91, 598 (holding

that the term “burglary” as used in the Armed Career Criminal Act

was to be given its “generic, contemporary meaning” to avoid a

scenario in which “a person . . . would, or would not, receive a

sentence enhancement based on exactly the same conduct, depending

on whether the State of his prior conviction happened to call that

conduct ‘burglary’”). We have adopted a generic definition of

attempt that conforms to the views set forth in the Model Penal Code

as the federal law of attempt within the Second Circuit. See United

States v. Manley, 632 F.2d 978, 987 (2d Cir. 1980) (“This Court . . . has

adopted the view set forth in . . . the American Law Institute’s Model

Penal Code . . . that the requisite elements of attempt are an intent to

engage in criminal conduct and the performance of acts which

constitute a ‘substantial step’ towards the commission of the

substantive offense.”); see also Tabb, 949 F.3d at 86 (“[G]eneric attempt

is ‘the presence of criminal intent and the completion of a substantial

31
step toward committing the crime.’” (quoting Sui, 250 F.3d at 115)).

This generic definition of attempt requires proof that the defendant

“had the intent to commit the crime.” United States v. Crowley, 318

F.3d 401, 407 (2d Cir. 2003); see also 2 Wayne R. LaFave, Substantive

Criminal Law § 11.3(a) (3d ed. 2021) (“The mental state required for the

crime of attempt, as it is customarily stated in the cases, is an intent to

commit some other crime.”). And under this generic definition, “[t]he

crime of attempt requires that the defendant have intended to commit

each of the essential elements of the substantive crime.” Collier v.

United States, 989 F.3d 212, 221 (2d Cir. 2021); see also LaFave,

Substantive Criminal Law § 11.3(a) (noting that “because intent is

needed for the crime of attempt,” crimes that “are defined in terms of

acts causing a particular result” cannot be attempted unless the

defendant specifically intended to bring about that result). Castillo’s

conviction for attempted second-degree gang assault reflects the

nonsensical mens rea of intent to cause unintended serious physical

32
injury. His conviction therefore cannot reflect that he specifically

intended each element of the object offense, and it therefore does not

satisfy the definition of generic attempt. Castillo’s conviction is thus

not covered by Application Note 1.

b. The enumerated offenses clause

The Government also argues that, even if attempted second-

degree gang assault is not a crime of violence under U.S.S.G.

§ 4B1.2(a)(1), the force clause, it nonetheless qualifies as a crime of

violence under § 4B1.2(a)(2), the enumerated offenses clause. We also

use the categorical approach to determine whether a prior conviction

is a crime of violence under the enumerated offenses clause. See

United States v. Evans, 924 F.3d 21, 25 (2d Cir. 2019). “To do so, we

‘compare the elements of the statute forming the basis of the

defendant’s conviction with the elements of the ‘generic’

[enumerated] crime—i.e., the offense as commonly understood.’” Id.

(quoting Descamps v. United States, 570 U.S. 254, 257 (2013)). The

“generic” meaning of the enumerated offense is to be “ascertain[ed]

33
‘in many instances’ by reference to ‘the sense in which the term is now

used in the criminal codes of most States,’ but also by ‘consulting

other sources, including federal criminal statutes, the Model Penal

Code, scholarly treatises, and legal dictionaries.’” Scott, 990 F.3d at

123 (alterations omitted) (quoting United States v. Castillo, 896 F.3d

141, 150 (2d Cir. 2018)). “If the offense matches or is narrower than

the generic version, a conviction under the statute categorically

qualifies as a predicate crime of violence offense.” Moore, 916 F.3d at

237–38. However, if “the statute criminalizes any conduct that would

not fall within the scope of the generic offense, the offense cannot be

considered a crime of violence.” Id. at 238. As relevant here, the list

of enumerated offenses in U.S.S.G. § 4B1.2(a)(2) includes “aggravated

assault.”

The Government argues that the generic definition of

aggravated assault is the definition provided by Model Penal Code

§ 211.1. Under the Model Penal Code, a person is guilty of aggravated

34
assault if he “(a) attempts to cause serious bodily injury to another, or

causes such injury purposely, knowingly or recklessly under

circumstances manifesting extreme indifference to the value of

human life; or (b) attempts to cause or purposely or knowingly causes

bodily injury to another with a deadly weapon.” Model Penal Code

§ 211.1(2)(a)–(b).

The Government first argues that the statute under which

Castillo was convicted, “Section 120.06[,] requires that the defendant

‘cause[] serious physical injury.’” Gov’t Br. at 27. True, the completed

offense of second-degree gang assault requires the causation of

“serious physical injury,” but, unlike the Model Penal Code, the New

York statute allows for a conviction even where the defendant

intended to cause only physical injury and thus the causation of

serious physical injury was unintentional. In re Cisely G., 918 N.Y.S.2d

at 24 (“[S]econd-degree gang assault involves the intended result of

physical injury and the unintended result of serious physical

35
injury . . . .”). And Castillo’s conviction was not for completed

second-degree gang assault, but for attempted second-degree gang

assault and therefore did not involve the actual causation of serious

physical injury. In any event, Castillo’s conviction does not align with

the Model Penal Code’s definition of “attempt[ing] to cause serious

bodily injury to another,” Model Penal § 211.1(2)(a), because the

Model Penal Code defines attempt as “do[ing] or omit[ting] to do

anything with the purpose of causing or with the belief that it will

cause such result without further conduct on his part,” id. § 5.01(1)(b).

Finally, neither attempted nor completed second-degree gang assault

has as an element the causation of bodily injury “with a deadly

weapon,” and so Castillo’s conviction does not satisfy Model Penal

Code § 211.1(2)(b). 6 We therefore conclude that Castillo’s conviction

6 The government’s citation of Sanchez for the proposition that “New York
Courts consider [gang] assaults to be ‘tantamount’ to assaults with a deadly
weapon,” Gov’t Br. 27 (quoting Sanchez, 13 N.Y.3d at 565) (internal citation
omitted), does not convince us otherwise. The Sanchez court’s quotation from the
legislative history of the gang assault statute does not satisfy the strictures of the
categorical approach.

36
for attempted gang assault is not categorically “aggravated assault”

within the meaning of U.S.S.G. § 4B1.2(a)’s enumerated offenses

clause.

III. Conclusion

Our decision today—that an attempted assault conviction is not

a “crime of violence”—may seem anomalous. But if an anomaly

exists, it is one that results at least in part from the rigidity of the

categorical approach. As multiple members of this Court have

pointed out in various contexts, the categorical approach sometimes

generates strange results. See Chery v. Garland, 16 F.4th 980, 990–92

(2d Cir. 2021); Scott, 990 F.3d at 125–26 (Park, J., concurring).

However, unless and until Congress or the Supreme Court takes

action to identify an alternative approach to define the contours of

which prior convictions may be used to enhance a defendant’s

sentence, we are bound to apply it. Our decision today is therefore

“likely but the latest in an unending procession of . . . cases applying

the categorical approach.” Chery, 16 F.4th at 991.

37
 We also emphasize that our holding today is a narrow one—

that attempted second-degree gang assault in violation of N.Y. Penal

Law §§ 120.06 and 110.00 is not a crime of violence under U.S.S.G.

§ 4B1.2. We need not and do not today hold that a legally impossible

crime can never satisfy the requirements of § 4B1.2. Nor do we

express any view on what the proper outcome would be where a

legally impossible crime has an element that can be coherently read

to establish a defendant’s use, attempted use, or threatened use of

physical force. We are bound to conclude that Castillo’s New York

state conviction is not a crime of violence because the elements of

attempt are irreconcilable with the elements of second-degree gang

assault under state law. We of course express no view on whether

any other jurisdictions (state or federal) would take the same

approach.

In sum, we hold as follows:

38
(1) Castillo’s conviction for attempted second-degree gang

assault is not a crime of violence within the meaning of

U.S.S.G. § 4B1.2(a)’s force clause, § 4B1.2(a)(1). We can

discern no coherent element that constitutes the use,

attempted use, or threatened use of physical force. It was

error for the district court to conclude otherwise.

(2) Castillo’s intent to have the presence and aid of others

actually present does not categorically involve the use,

attempted use, or threatened use of physical force.

(3) Castillo’s conviction does not fall within the definition of

“attempt[]” as that term is used in Application Note 1 to

U.S.S.G. § 4B1.2 because it does not reflect that he

specifically intended each element of the object crime of

second-degree gang assault.

39
 (4) Attempted second-degree gang assault is not enumerated

“aggravated assault” as that phrase is used in U.S.S.G.

§ 4B1.2(a)’s enumerated offenses clause, § 4B1.2(a)(2).

We therefore VACATE Castillo’s sentence and REMAND for

resentencing.

40