United States v. Ragonese

47 F.4th 106

UNITED STATES of America, Appellee,

v.Ryan RAGONESE, Defendant-Appellant.

Docket No. 20-3371-cr

August Term, 2021

United States Court of Appeals, Second Circuit.

Argued: December 8, 2021

Decided: August 31, 2022

Daniel H. Wolf, Assistant United States Attorney (Christine I. Magdo, Won S. Shin, Assistant United States Attorneys, on the brief), for Audrey Strauss, United States Attorney for the Southern District of New York, New York, NY, for Appellee;

Colleen P. Cassidy, Federal Defenders of New York, Inc., New York, NY, for Defendant-Appellant.

Before: Sack, Lynch, and Bianco, Circuit Judges.

Sack, Circuit Judge:

Ryan Ragonese pled guilty to two counts of receiving and possessing child pornography after law enforcement agents found eighty-six videos depicting child pornography on his cell phone. The district court (Paul A. Crotty, Judge ) applied sentencing enhancements under 18 U.S.C. § 2252A(b)(1) and (b)(2), which increase the mandatory minimum sentence if the defendant has a prior conviction "under the laws of any State relating to aggravated sexual abuse, sexual abuse, or abusive sexual conduct involving a minor or ward." Id. Ragonese was previously convicted in New York for attempted sodomy in the first degree against an eight-year-old victim. N.Y. Penal Law § 130.50 (1965). The New York statute prohibited, in relevant part, "engag[ing] in deviate sexual intercourse with another person ... [w]ho is less than eleven years old." Id.

Ragonese argues that the sentencing enhancements under § 2252A(b)(1) and (b)(2) are inapplicable under a modified categorical approach. Specifically, he contends that his prior conviction does not "relat[e] to" the sexual abuse of a minor, because the New York statute does not require that the offense be committed for the purpose of sexual gratification. Ragonese further argues that a broader interpretation of "relating to" would be unconstitutionally vague. For the reasons set forth below, we AFFIRM the judgment of the district court.

BACKGROUND

Factual Background

On April 24, 2018, Ryan Ragonese uploaded a video to an Instagram account that depicted an adult male engaging in oral sex with a minor who was approximately eight to ten years old. On February 21, 2019, Ragonese participated in a voluntary interview with law enforcement agents, and he admitted to possessing the video and controlling the Instagram account. The agents executed a search of Ragonese's cell phone, where they found a recently deleted "note" containing a hyperlink to a cloud storage folder that held eighty-six videos depicting child pornography. The videos involved minors between the ages of six and eighteen. Ragonese admitted that he obtained some of these videos by posing as an adolescent on social media and soliciting explicit material from minors.

Procedural History

On March 4, 2019, Ragonese was indicted on one count of receipt of child pornography, in violation of 18 U.S.C. §§ 2252A(a)(2)(B), (b)(1), and 2, and one count of possession of child pornography, in violation of 18 U.S.C. §§ 2252A(a)(5)(B), (b)(2), and 2.

On June 28, 2019, Ragonese moved for a preliminary ruling on whether a previous conviction reflected in his record triggered the federal sentencing enhancements under 18 U.S.C. § 2252A. The sentencing enhancements apply if, in relevant part, the defendant "has a prior conviction ... under the laws of any State relating to aggravated sexual abuse, sexual abuse, or abusive sexual conduct involving a minor or ward." 18 U.S.C. § 2252A(b)(1) and (b)(2). For convictions under § 2252A(a)(2), the sentencing enhancement increases the mandatory minimum sentence from five years to fifteen years. Id. § 2252A(b)(1). For convictions under § 2252A(a)(5), the sentencing enhancement increases the mandatory minimum sentence from zero years to ten years. Id. § 2252A(b)(2).

Ragonese was previously convicted in 1996 for attempted sodomy in the first degree under New York law. N.Y. Penal Law § 130.50 (1965) (" Section 130.50"). Section 130.50 prohibited "engag[ing] in deviate sexual intercourse with another person: (1) By forcible compulsion; or (2) Who is incapable of consent by reason of being physically helpless; or (3) Who is less than eleven years old."¹ Id. The statute defined "deviate sexual intercourse" as "sexual conduct between persons not married to each other consisting of contact between the penis and the anus, the mouth and penis, or the mouth and the vulva." N.Y. Penal Law § 130.00(2) (1984). Ragonese was twenty-three years old at the time of the offense conduct, and the victim was the eight-year-old daughter of Ragonese's friend.

Before the district court, Ragonese argued that the sentencing enhancements should not apply because Section 130.50 is not limited to conduct undertaken for the purpose of sexual gratification. Therefore, Ragonese argued, Section 130.50 does not "relat[e] to" the sexual abuse of a minor and cannot qualify as a predicate offense. See 18 U.S.C. § 2252A(b)(1) and (b)(2). The district court rejected these arguments, concluding that because Section 130.50 "proscribes non-consensual sexual acts with a minor," United States v. Ragonese , No. 19-cr-154, 2019 U.S. Dist. LEXIS 154011, at *5 (S.D.N.Y. Sept. 10, 2019) (quoting United States v. Barker , 723 F.3d 315, 324 (2d Cir. 2013) ), Ragonese's prior conviction " ‘relate[s] to’ ‘abusive sexual conduct involving a minor’ as that phrase is ordinarily understood and thus, triggers the penalty enhancements," id. at *9.

On July 29, 2020, Ragonese pled guilty to both counts in the indictment. Consistent with its ruling that the sentencing enhancements under § 2252A(b)(1) and (b)(2) apply, the district court sentenced Ragonese to two concurrent terms of 180 months’ imprisonment, to be followed by five years of supervised release.

Ragonese appealed.

DISCUSSION

I. Standard of Review

"We review de novo all questions of law relating to the district court's application of a sentencing enhancement." United States v. Kleiner , 765 F.3d 155, 158 (2d Cir. 2014) (internal quotation marks omitted).

Ragonese also raises a vagueness challenge for the first time on appeal, which we review for plain error. See United States v. Napout , 963 F.3d 163, 182-83 (2d Cir. 2020). "Under plain error review, an appellant must demonstrate that ‘(1) there is an error; (2) the error is clear or obvious, rather than subject to reasonable dispute; (3) the error affected the appellant's substantial rights, which in the ordinary case means it affected the outcome of the district court proceedings; and (4) the error seriously affects the fairness, integrity or public reputation of judicial proceedings.’ " Id. at 183 (quoting United States v. Marcus , 560 U.S. 258, 262, 130 S.Ct. 2159, 176 L.Ed.2d 1012 (2010) ).

II. Application of the Sentencing Enhancements under 18 U.S.C. § 2252A(b)(1) and (b)(2)

To determine whether a prior conviction qualifies as a predicate offense for a federal sentencing enhancement, we apply what is known as the categorical approach or modified categorical approach. See Descamps v. United States , 570 U.S. 254, 257-65, 133 S.Ct. 2276, 186 L.Ed.2d 438 (2013) ; United States v. Simard , 731 F.3d 156, 161 (2d Cir. 2013). Under these approaches, we must "consider whether [the defendant's] state conviction meets the elements of the applicable [federal] generic offense." Barker , 723 F.3d at 321. In doing so, "[s]entencing courts may ‘look only to the statutory definitions’—i.e. , the elements—of a defendant's prior offenses, and not ‘to the particular facts underlying those convictions.’ " Descamps , 570 U.S. at 261, 133 S.Ct. 2276 (quoting Taylor v. United States , 495 U.S. 575, 600, 110 S.Ct. 2143, 109 L.Ed.2d 607 (1990) ).

The categorical approach applies when the state offense has a "single, indivisible set of elements," such that the sentencing court can simply "compare the statute forming the basis of the defendant's prior conviction with the applicable generic offense in the federal sentencing statute." Barker , 723 F.3d at 319-20. The modified categorical approach applies "when a divisible statute, listing potential offense elements in the alternative, renders opaque which element played a part in the defendant's [prior] conviction." Descamps , 570 U.S. at 260, 133 S.Ct. 2276. Under those circumstances, the sentencing court may consider facts underlying the prior conviction only to the extent necessary to determine the particular provision of state law under which the defendant was convicted. Barker , 723 F.3d at 319-20. "Once the district court has identified the particular provision of state law under which the defendant was convicted, the district court must then compare the elements of that provision to the generic federal sentencing enhancement to determine its applicability just as it would under a categorical approach." Id. at 320.

Here, the parties do not dispute that the modified categorical approach applies, because Ragonese's prior conviction was based on a divisible statute that listed potential offense elements in the alternative. See N.Y. Penal Law § 130.50 (1965) (criminalizing three different forms of deviate sexual intercourse). The parties also do not dispute that Ragonese's conviction was under Section 130.50(3), which criminalized deviate sexual intercourse with a child who is less than eleven years old.

But the specific sentencing enhancements at issue provide a twist. They are triggered not only when the prior conviction matches an enumerated offense in the federal penalty provision – "aggravated sexual abuse, sexual abuse, or abusive sexual conduct involving a minor or ward" – but also when the prior conviction "relate[s] to" such offenses. 18 U.S.C. § 2252A(b)(1) and (b)(2). Ragonese argues that his 1996 conviction does not "relat[e] to" the sexual abuse of a minor, because Section 130.50 does not require that the crime be committed "for the purpose of sexual gratification." Appellant's Br. 10. According to Ragonese, ...