United States v. Kroll In the

No. 16‐4310
United States v. Kroll
In the 1
United States Court of Appeals 2
For the Second Circuit 3
4
5
August Term, 2017 6
No. 16‐4310 7
8
U NITED S TATES OF AMERICA, 9
Appellee, 10
11
v. 12
13
JAY K ROLL, 14
Defendant‐Appellant. 15
16
17
Appeal from the United States District Court 18
for the Eastern District of New York. 19
No. 12‐cr‐411 — Leonard D. Wexler, Judge. 20
21
22
A RGUED: MAY 3, 2018 23
D ECIDED: MARCH 5, 2019 24
25
Before: LEVAL, L YNCH , and D RONEY , Circuit Judges. 26
27
28
Appeal from a judgment of the United States District Court for 29
the Eastern District of New York (Wexler, J.) sentencing Defendant‐ 30
Appellant Jay Kroll to mandatory life imprisonment. The district 31

-- 1 of 30 --

2
court concluded that a life sentence was mandatory for Kroll’s 1
convictions under 18 U.S.C. § 2251(a) and § 2251(e) because it found 2
Kroll’s prior New York state conviction was a “prior sex conviction” 3
under 18 U.S.C. § 3559(e). Kroll contends that the district court 4
committed plain error by failing to apply the categorical approach to 5
that conviction. We agree. Under the categorical approach, Kroll’s 6
conviction does not qualify as a “prior sex conviction” under § 3559(e) 7
because the state statute under which he was convicted sweeps more 8
broadly than its federal equivalent. Accordingly, we VACATE the 9
district court’s judgment and REMAND the cause to the district court 10
for resentencing. 11
12
13
S ARITHA K OMATIREDDY , Assistant 14
United States Attorney (Amy Busa, 15
Artie McConell, Assistant United 16
States Attorneys, on the brief), for 17
Richard P. Donoghue, United States 18
Attorney for the Eastern District of 19
New York, Brooklyn, NY, for Appellee. 20
21
R OBERT A. C ULP , Garrison, NY, for 22
Defendant‐Appellant. 23
D RONEY , Circuit Judge: 24
Defendant‐Appellant Jay Kroll appeals his sentence of life 25
imprisonment based on his guilty plea to two counts of sexual 26
exploitation of a child in violation of 18 U.S.C. § 2251(a) and § 2251(e). 27
At sentencing, the district court concluded that a life sentence was 28

-- 2 of 30 --

3
mandatory based on its determination that Kroll’s prior conviction 1
from 1993 for sodomy in the second degree under New York law was 2
a “prior sex conviction” under 18 U.S.C. § 3559(e). Kroll contends that 3
the district court plainly erred in that determination by failing to 4
apply the “categorical approach,” which requires comparing the New 5
York statute under which he was convicted with its equivalent federal 6
criminal statute. 7
We agree. We held in United States v. Rood that the categorical 8
approach applies to 18 U.S.C. § 3559(e). 679 F.3d 95, 98 (2d Cir. 2012) 9
(per curiam) (“In order to determine whether a state offense is 10
equivalent to a federal offense, courts must compare the elements of 11
the state offense to the elements of the federal offense.”). Under the 12
categorical approach, a prior state conviction qualifies as a “prior sex 13
conviction” under § 3559(e) only if “the least of conduct made 14
criminal by the state statute [of conviction] falls within the scope of 15
activity” punishable under one of the statutes constituting a “Federal 16

-- 3 of 30 --

4
sex offense.” Stuckey v. United States, 878 F.3d 62, 67 (2d Cir. 2017). 1
Accordingly, the district court erred in considering Kroll’s underlying 2
conduct to determine whether his 1993 conviction constituted a “prior 3
sex conviction.” Applying the categorical approach, Kroll’s 1993 4
conviction does not qualify as a “prior sex conviction” under § 3559(e) 5
because the state statute under which he was convicted sweeps more 6
broadly than its federal equivalent. 7
BACKGROUND 8
On multiple occasions from June to December 2011, Kroll 9
sexually abused a twelve‐year‐old boy in New York and 10
Pennsylvania and produced sexually explicit photographs and video 11
of himself and the child. Kroll was indicted by a grand jury in the 12
United States District Court for the Eastern District of New York for 13
two counts of sexual exploitation of a child in violation of 18 U.S.C. 14
§ 2251(a) and § 2251(e) (“Count One” and “Count Two”), possession 15
of child pornography in violation of 18 U.S.C. § 2252(a)(4)(B) and § 16

-- 4 of 30 --

5
2252(b)(2) (“Count Three”), and committing Counts One and Two as 1
a registered sex offender in violation of 18 U.S.C. § 2260A (“Count 2
Four”).1 3
Because Kroll had a particular prior New York state sex offense 4
conviction, the government sought a life sentence for Counts One and 5
Two pursuant to 18 U.S.C. § 3559(e)(1). Section 3559(e)(1) mandates 6
a life sentence upon conviction for certain sex offenses (including 7
those charged under Counts One and Two) if the defendant has a 8
“prior sex conviction” in which a minor was the victim. 18 U.S.C. § 9
3559(e)(1). 10
The circumstances of Kroll’s prior New York state conviction 11
are as follows. On March 8, 1993, Kroll pleaded guilty in the County 12
Court of the State of New York, Sullivan County, to sodomy in the 13
1 Counts One and Two involved the same minor victim. Count One concerned
activity within the Western and Eastern Districts of New York between June and
December 2011, and Count Two involved activity within the Eastern District of
New York and the Western District of Pennsylvania in July 2011.

-- 5 of 30 --

6
second degree in violation of New York Penal Law § 130.45. In 1993, 1
New York Penal Law § 130.45 applied to conduct with a minor under 2
the age of fourteen. N.Y. Penal Law § 130.45 (1965) (amended 2000, 3
2003).2 4
At a hearing on September 22, 2014, shortly before the federal 5
trial was scheduled to begin, Kroll moved to proceed pro se. As part 6
of the district court’s colloquy with Kroll to determine if he knowingly 7
and voluntarily waived his right to counsel, the court asked Kroll if 8
he knew that the court “must impose life imprisonment” if Kroll were 9
found guilty of either Count One or Count Two. Joint App’x at 40. 10
Kroll responded that he did know. The court granted Kroll’s motion, 11
2 The full text of the statute as it existed in 1993 is as follows:
A person is guilty of sodomy in the second degree when, being
eighteen years old or more, he engages in deviate sexual
intercourse with another person less than fourteen years old.
Sodomy in the second degree is a class D felony.
N.Y. Penal Law § 130.45 (1965).

-- 6 of 30 --

7
appointed his former counsel as standby counsel, and adjourned the 1
trial date. 2
Kroll ultimately pleaded guilty to all four counts of the 3
indictment.3 At his guilty plea hearing on May 15, 2015, he stipulated 4
that the prior New York state conviction involved an eleven‐year‐old 5
boy. The United States Magistrate Judge informed Kroll that a life 6
sentence was “both the minimum and the maximum” sentence for 7
Counts One and Two, and Kroll stated that he understood. Joint 8
App’x at 60–61. The district court accepted Kroll’s guilty plea, as the 9
magistrate judge had recommended, and on December 14, 2016, the 10
district court sentenced him to concurrent life sentences on Counts 11
One and Two; twenty years on Count Three, concurrent with Counts 12
One and Two; and ten years on Count Four, to be served 13
consecutively to the life sentences. 14
3 There was no plea agreement.

-- 7 of 30 --

8
At the sentencing proceeding, Kroll’s standby counsel argued 1
that a life sentence was not justified. The district court disagreed, 2
stating: 3
Normally, I agree that giving someone a life sentence 4
who didn’t kill somebody seems irrational. Th[is is] one 5
of the exceptions. Based upon what I have heard and 6
what I have read, the torture [to Kroll’s victims] is 7
lifetime. The punishment is equal to that. The sentence 8
of the court[:] Count One, life. Count Two, life. Both to 9
run concurrently. And that is the law. I have no 10
authority to go under that, even if I wanted to, which I 11
don’t. 12
Joint App’x at 139. The district court gave no further explanation for 13
the life sentences on Counts One and Two. 14
Notwithstanding the request for a lesser sentence by his 15
standby counsel, Kroll did not object at his sentencing to the legal 16
applicability of the mandatory life sentence provided by 18 U.S.C. 17
§ 3559(e). On appeal, however, Kroll contends that the district court 18
erred in concluding that his 1993 conviction was a “prior sex 19
conviction” within the meaning of § 3559(e)(1) because the New York 20

-- 8 of 30 --

9
statute under which he was convicted in 1993 punishes a broader 1
range of conduct than the most comparable federal sex offense. 2
DISCUSSION 3
We first address whether, as Kroll contends, the categorical 4
approach applies to determine whether his 1993 state conviction 5
triggered the mandatory life sentence provision in 18 U.S.C. § 3559(e). 6
Then, we consider whether Kroll waived his right to challenge the 7
applicability of § 3559(e) and, finally, whether the district court 8
committed plain error by failing to apply the categorical approach. 9
A. The Categorical Approach Applies to Kroll’s Offenses 10
Section 3559(e)(1) states in relevant part that “[a] person who is 11
convicted of a Federal sex offense in which a minor is the victim shall 12
be sentenced to life imprisonment if the person has a prior sex 13
conviction in which a minor was the victim.” 18 U.S.C. § 3559(e)(1). 14
A “Federal sex offense” is an offense under one of several enumerated 15
federal statutes, including 18 U.S.C. § 2251, under which Kroll was 16

-- 9 of 30 --

10
convicted of Counts One and Two. Id. § 3559(e)(2)(A). Thus, we must 1
determine whether Kroll’s 1993 state conviction is a “prior sex 2
conviction” for purposes of § 3559(e)(1)’s sentencing enhancement. 3
A “prior sex conviction” comprises either a “Federal sex 4
offense” as defined in § 3559(e)(2)(A), or, as is relevant here, a “State 5
sex offense” as defined in § 3559(e)(2)(B). 18 U.S.C. § 3559(e)(2)(C). 6
For a prior state conviction to qualify as a “State sex offense,” it must 7
“consist[] of conduct that would be a Federal sex offense” if there 8
were a basis for federal jurisdiction. 18 U.S.C. § 3559(e)(2)(B). Of the 9
enumerated Federal sex offenses under § 3559(e)(2)(A), we agree with 10
the parties that 18 U.S.C. § 2241(c) is the most comparable to New 11
York Penal Law § 130.45. 12
When Kroll was convicted of the state offense of sodomy in the 13
second degree in 1993, New York Penal Law § 130.45 stated that “[a] 14
person is guilty of sodomy in the second degree when, being eighteen 15
years old or more, he engages in deviate sexual intercourse with 16

-- 10 of 30 --

11
another person less than fourteen years old.” N.Y. Penal Law 1
§ 130.45. By contrast, 18 U.S.C. § 2241(c) applies to a defendant who 2
“knowingly engages in a sexual act with another person who has not 3
attained the age of 12 years . . . or attempts to do so.” 4 18 U.S.C. 4
§ 2241(c). The state statute thus punishes some conduct that the 5
federal statute does not: deviate sexual intercourse with twelve‐ and 6
thirteen‐year‐old children. As mentioned above, Kroll stipulated at 7
his plea proceeding in the instant case that his victim in the 1993 state 8
offense was eleven years old, below the age limit for both statutes. 9
Therefore, whether Kroll’s 1993 conviction is a “prior sex conviction” 10
turns on whether we look to the statutory elements of the prior 11
conviction or to his conduct underlying that conviction, as admitted 12
in the guilty‐plea stipulation in this case. 13
4 Section 2241(c) also applies to a defendant who knowingly engages in a sexual
act with a person between the ages of twelve and fifteen through force, threat of
force, or various forms of incapacitation. Id. § 2241(c); see id. § 2241(a), (b). The
government does not argue that this portion of § 2241(c) is relevant here.

-- 11 of 30 --

12
In United States v. Rood, 679 F.3d 95 (2d Cir. 2012), we addressed 1
how to determine whether a prior state conviction consists of conduct, 2
which, but for the additional element of federal jurisdiction, would be 3
a “Federal sex offense,” and thus constitutes both a “State sex offense” 4
under 18 U.S.C. § 3559(e)(2)(B) and makes a conviction for that 5
conduct a “prior sex conviction” under 18 U.S.C. § 3559(e)(2)(C). 679 6
F.3d at 98. Looking to the text of § 3559(e), we stated that “[i]n order 7
to determine whether a state offense is equivalent to a federal offense, 8
courts must compare the elements of the state offense to the elements 9
of the federal offense.” Id. (citing 18 U.S.C. § 3559(e)(2)(B)). In other 10
words, to this extent, the Rood court adopted a categorical approach. 11
Under the categorical approach, we “ask[] whether the least of 12
conduct made criminal by the state statute falls within the scope of 13
activity that the federal statute penalizes.” Stuckey, 878 F.3d at 67. “If 14
the state statute sweeps more broadly” than the federal statute—“i.e., 15
it punishes activity that the federal statute does not encompass—then 16

-- 12 of 30 --

13
the state crime cannot count as a predicate [offense].” Id. (internal 1
quotation marks and citation omitted). 2
The categorical approach is distinct from the conduct‐specific 3
approach, under which courts “look[] to the facts of the specific 4
[prior] case” to determine whether the conduct underlying a 5
predicate conviction qualifies for a sentencing enhancement under 6
the federal statute. United States v. Barrett, 903 F.3d 166, 173 n.3 (2d 7
Cir. 2018). Here, the government argues that we should abandon the 8
categorical approach applied in Rood in favor of the conduct‐specific 9
approach, because the language of § 3559(e), which refers to the 10
“conduct” of the defendant, requires it. However, Rood’s application 11
of the categorical approach to § 3559(e) has only been reinforced by 12
subsequent precedent and remains binding on us. 13
Indeed, in Mathis v. United States, the Supreme Court 14
interpreted a phrase similar to § 3559(e)’s “prior . . . convictions” 15
language: the Armed Career Criminal Act’s (“ACCA”) requirement 16

-- 13 of 30 --

14
of a sentencing enhancement for individuals with three “previous 1
convictions” for violent felonies. 136 S. Ct. 2243, 2252 (2016). The 2
Court found that the ACCA’s emphasis on “convictions” directed 3
sentencing courts to “ask only about whether the defendant had been 4
convicted of crimes falling within certain categories, and not about 5
what the defendant had actually done.” Id. (internal quotation marks 6
and citations omitted). The Court distinguished the use of the word 7
“convictions” in the ACCA from language in statutes requiring a 8
conduct‐specific approach, such as those imposing a sentencing 9
enhancement for a prior “offense committed” by the defendant.5 Id. 10
(alterations, internal quotation marks, and citation omitted) 11
(“Congress well knows how to instruct sentencing judges to look into 12
the facts of prior crimes.”). 13
5 The use of the categorical approach in the ACCA context has been repeatedly
affirmed by the Supreme Court, including recently. See Stokeling v. United States,
139 S. Ct. 544, 549‐50 (2019) (applying the categorical approach to determine
whether the defendant qualifies for a mandatory minimum sentence under the
ACCA); United States v. Stitt, 139 S. Ct. 399, 405 (2018) (same).

-- 14 of 30 --

15
The government attempts to distinguish Mathis by arguing that 1
§ 3559 defines “prior sex conviction” with reference to the offense 2
“conduct,” which, it contends, suggests a conduct‐specific approach. 3
However, the Supreme Court rejected a similar argument in Johnson 4
v. United States, 135 S. Ct. 2551 (2015). There, the Court examined a 5
provision of the ACCA defining a “violent felony” as a crime that 6
“involves conduct that presents a serious or potential risk of physical 7
injury to another.” Id. at 2555 (emphasis added). Justice Alito, in 8
dissent, urged the Court to apply a conduct‐specific approach to that 9
clause in order to save it from being struck down as 10
unconstitutionally vague. Id. at 2578–80 (Alito, J., dissenting). The 11
majority rejected that approach, instead finding that the categorical 12
approach was the “only plausible interpretation of the law.” Id. at 13
2562 (quoting Taylor v. United States, 495 U.S. 575, 602 (1990)). 14
In addition, the Mathis Court observed that the categorical 15
approach “avoids unfairness to defendants” by preventing courts in 16

-- 15 of 30 --

16
subsequent prosecutions from relying on non‐elemental facts that 1
may be “prone to error precisely because their proof is unnecessary” 2
at the time of the prior conviction. Mathis, 136 S. Ct. at 2253 (citation 3
omitted). Where the truth of a fact made no difference in the 4
underlying case, the defendant “ha[s] no incentive to contest what 5
does not matter under the law,” and in fact “may have good reason 6
not to.” Id. (internal quotation marks and citation omitted); see also 7
Descamps v. United States, 570 U.S. 254, 270 (2013) (stating, for 8
example, that “during plea hearings, the defendant may not wish to 9
irk the prosecutor or court by squabbling about superfluous factual 10
allegations”). 11
Moreover, in United States v. Barrett, this Court recently found 12
that practical and constitutional reasons weigh heavily in favor of 13
applying the categorical approach over the conduct‐specific approach 14
where a sentencing enhancement statute requires “judicial 15
identification of what crimes . . . of prior conviction fit federal 16

-- 16 of 30 --

17
definitions of [predicate] crimes so as to expose a defendant to 1
enhanced penalties or other adverse consequences in subsequent 2
federal proceedings.” Barrett, 903 F.3d at 181 (emphasis omitted). 3
The categorical approach has certain practical advantages 4
where a federal court applies a sentencing enhancement provision 5
based on a prior state conviction. District courts will often face 6
difficulties ascertaining the nature of the conduct underlying a prior 7
conviction that could be decades old. See Taylor, 495 U.S. at 601; 8
United States v. Beardsley, 691 F.3d 252, 260 (2d Cir. 2012). Most 9
important, a court’s attempt to determine facts about that conduct 10
from a limited past record raises serious constitutional concerns. See 11
Descamps, 570 U.S. at 269. The Sixth Amendment requires that “only 12
a jury, and not a judge, may find facts that increase a maximum 13
penalty, except for the simple fact of a prior conviction.” Mathis, 136 14
S. Ct. at 2252 (citing Apprendi v. New Jersey, 530 U.S. 466, 490 (2000)). 15

-- 17 of 30 --

18
Thus, Rood’s application of the categorical approach to § 3559(e) 1
remains binding on us, and for good reasons.6 2
The government contends that the analytic step taken by the 3
Rood court after its comparison of the elements of the state and federal 4
statutes justified the district court in this case relying on certain 5
documents related to Kroll’s 1993 conviction to determine whether 6
the § 3559(e) sentencing enhancement was warranted. We disagree. 7
6 In the alternative, the government contends that § 3559(e) is “a hybrid statute,
requiring a comparison of certain elements under a categorical approach . . . but
an examination of conduct to satisfy other elements of the statute.” Appellee’s Br.
at 24. Section 3559(e)(1) lists two requirements for a predicate offense to qualify
for sentencing enhancement: (1) that the predicate offense constitute a “prior sex
conviction” as defined by § 3559(e)(2); and (2) that “a minor”—a person under
seventeen years of age—“was the victim” of the predicate offense. 18 U.S.C. §
3559(e)(1‐2). As advocated by the government, the Ninth Circuit has taken a
“hybrid” approach to those requirements, applying a categorical approach to
determine whether a predicate offense is a “prior sex conviction,” and applying a
conduct‐specific approach to determine whether “a minor was the victim” of the
predicate offense. United States v. Doss, 630 F.3d 1181, 1197–97 (9th Cir. 2011), as
amended on reh’g in part (Mar. 15, 2011) (quoting 18 U.S.C. § 2559(e)(1)).
Here, the only issue is whether Kroll’s 1993 offense qualifies as a “prior sex
conviction”—a question to which the categorical approach applies. We need not
reach the question of whether a different approach applies to aspects of § 3559 not
at issue.

-- 18 of 30 --

19
In Rood, “[i]n order to determine whether [the] state offense 1
[was] equivalent to [the] federal offense,” the court first “compare[d] 2
the elements” of the two offenses. 679 F.3d at 98. It found that “[t]here 3
is . . . a category of [the state offense] that would not constitute a 4
federal offense,” such that the elements of the state offense did not 5
categorically fit the federal offense. However, rather than stopping 6
its analysis there, concluding that the state conviction was not a 7
predicate conviction, Rood concluded that “the District Court could 8
not have determined from the statutory language alone whether the 9
offenses were equivalent,” id., and faulted the district court for failing 10
“to analyze whether the facts underlying the state conviction satisfied 11
the elements of the federal statute,” id. at 99‐100. It then went on to 12
examine the limited class of documents described by Shepard v. United 13
States, 544 U.S. 13 (2005)—also known as “Shepard documents,” see 14
United States v. Genao, 869 F.3d 136, 145 (2d Cir. 2017)—in order to 15
“analyze whether the facts underlying the state conviction satisfied 16

-- 19 of 30 --

20
the elements of the federal statute.” Rood, 679 F.3d at 99‐100. The 1
Rood court described that process as the “so‐called modified 2
categorical approach.” Id. at 98. 3
The Supreme Court later clarified that courts may look to 4
Shepard documents only where the state statute is divisible into 5
alternative elements, and only for the limited purpose of 6
“determin[ing] which alternative element . . . formed the basis of the 7
[predicate] conviction.” Descamps, 570 U.S. at 278. Descamps 8
described that inquiry as the “modified categorical approach.” Id. at 9
257‐58. Therefore, as we have recognized, Rood’s purported 10
application of the modified categorical approach “was erroneous in 11
two respects.” United States v. Barker, 723 F.3d 315, 321 (2d Cir. 2013) 12
(per curiam). “First, the modified categorical approach is ‘applicable 13
only to divisible statutes.’” Id. (quoting Descamps, 570 U.S. at 263). 14
Second, “the modified categorical approach simply provides a tool 15
enabling courts to discover the elements of the defendant’s prior 16

-- 20 of 30 --

21
conviction,” id., and may not be used to “analyze whether facts 1
underlying the state conviction satisfied the elements of the federal 2
statute,” id. (quoting Rood, 679 F.3d at 99‐100). 3
Although Rood’s version of the “modified categorical 4
approach” is no longer good law, its assertion that we apply the 5
categorical approach to § 3559(c) stands. Because the New York state 6
statute underlying Kroll’s predicate conviction prohibited sexual 7
conduct involving victims older than twelve years old, it swept more 8
broadly than the federal equivalent, 18 U.S.C. § 2241(c). See Esquivel‐ 9
Quintana v. Sessions, 137 S. Ct. 1562, 1568 (2017) (holding that there 10
was no categorical match where federal law proscribed sexual 11
intercourse with a person younger than sixteen, while the relevant 12
state statute proscribed sexual intercourse with a person younger 13
than eighteen). Therefore, the 1993 state conviction does not qualify 14
as a “prior sex conviction,” and it does not trigger the mandatory 15
enhancement of life imprisonment under 18 U.S.C. § 3559(e)(1). 16

-- 21 of 30 --

22
B. Kroll Did Not Waive His Challenge to the Application of 1
§ 3559(e)(1) 2
The government also contends that Kroll waived his challenge 3
to the application of § 3559(e)(1) by admitting that the conduct 4
underlying his New York conviction consisted of performing a sexual 5
act on an eleven‐year‐old. Even assuming that Kroll could waive his 6
challenge in these circumstances, we disagree that this admission 7
effected a waiver.7 8
“[W]aiver is the intentional relinquishment or abandonment of 9
a known right.” United States v. Olano, 507 U.S. 725, 733 (1993) (internal 10
quotation marks omitted) (emphasis added); see also United States v. 11
Dantzler, 771 F.3d 137, 146 n.5 (2d Cir. 2014) (explaining that waiver 12
analysis “focuse[s] on strategic, deliberate decisions that litigants 13
consciously make”). In United States v. Dantzler, we held that it was 14
error for the district court to rely on facts that the defendant provided 15
7 Because we conclude that Kroll did not knowingly and intentionally waive this
challenge, we need not decide whether a criminal defendant can waive the
application of the categorical approach.

-- 22 of 30 --

23
at the time of sentencing to determine that his prior offenses were 1
predicate crimes under the ACCA. 771 F.3d at 148–49. In so holding, 2
we rejected the government’s argument that the defendant waived his 3
challenge to the district court’s consideration of those facts because 4
the record did not indicate that either party contemplated whether the 5
facts could be considered or the potential effects of their introduction 6
on the application of the ACCA to the defendant’s sentence. Id. at 146 7
n.5. 8
The reasoning from Dantzler applies here. There is no 9
indication in the record that Kroll knew that, by stipulating to his 1993 10
victim’s age, he would give up the opportunity to challenge the 11
mandatory life sentences that would be imposed under Counts One 12
and Two through the categorical approach to § 3559(e). Indeed, the 13
record shows that the court and parties did not review applying the 14
categorical approach to the 1993 conviction, and at the September 22, 15
2014 hearing, the court told Kroll that a conviction on Count One or 16

-- 23 of 30 --

24
Two at trial would necessarily result in a mandatory life sentence. 1
Therefore, Kroll did not knowingly and intentionally waive his 2
objection. 3
C. The District Court Plainly Erred 4
Having concluded that Kroll did not waive his challenge to the 5
application of § 3559(e), we nonetheless apply plain error review 6
because Kroll did not raise this argument below. See United States v. 7
Broxmeyer, 699 F.3d 265, 279 (2d Cir. 2012) (finding that plain error 8
review applies to forfeited objections at sentencing). To find such an 9
error, we must determine that “(1) there was error, (2) the error was 10
plain, . . . (3) the error prejudicially affected [the defendant’s] 11
substantial rights,” and (4) “the error seriously affected the fairness, 12
integrity or public reputation of judicial proceedings.” United States 13
v. Torrellas, 455 F.3d 96, 103 (2d Cir. 2006) (alteration and internal 14
quotation marks omitted). All four elements of the standard are met 15
here. 16

-- 24 of 30 --

25
First, the court erred by concluding that Kroll’s 1993 conviction 1
was a “State sex offense” and thus a “prior sex conviction” under 2
§ 3559(e)(2). That is because, as discussed above, under the 3
categorical approach, the state statute underlying the 1993 conviction 4
was broader than 18 U.S.C. § 2241(c), the closest federal equivalent. 5
Second, the error was plain. Our decisions are clear that, under 6
the categorical approach, “to determine whether a state offense is 7
equivalent to a federal offense [under § 3559(e)(2)], courts must 8
compare the elements of the state offense to the elements of the 9
federal offense.” Rood, 679 F.3d at 98. After Descamps, our case law 10
made it equally clear that in following the categorical approach, “the 11
context and facts of the defendant’s crime” are not relevant to the 12
comparison except to “determine which alternative element in a 13
divisible statute formed the basis of the defendant’s conviction.” 14
Barker, 723 F.3d at 320 (internal quotation marks omitted). As 15
mentioned above, alternative elements in a divisible statute are not at 16

-- 25 of 30 --

26
issue here. Yet, the district court erroneously concluded it could 1
consider Kroll’s stipulated conduct to determine whether his 1993 2
conviction would have been punishable under § 2241(c). Cf. Dantzler, 3
771 F.3d at 146–148 (holding that it was plain error for the district 4
court to rely on materials that it was not allowed to consider in 5
determining that prior offenses were committed “on occasions 6
different from one another for purposes of sentencing under the 7
ACCA” (internal quotations omitted)). 8
Third, the erroneous determination that a life sentence was 9
mandatory prejudicially affected Kroll’s substantial rights because it 10
influenced the sentence he ultimately received. See United States v. 11
Sanchez, 773 F.3d 389, 391–93 (2d Cir. 2014) (holding that a defendant’s 12
substantial rights were prejudicially affected when the district court 13
erroneously concluded that his offense carried a mandatory 14
minimum of twenty years instead of ten, and both parties relied on 15
that error in arguing for an appropriate sentence). 16

-- 26 of 30 --

27
The government contends that Kroll did not suffer prejudice 1
because the district court’s comments at sentencing demonstrate that 2
it would have given Kroll a life sentence even if it had concluded it 3
had the discretion not to do so. The Supreme Court has held that “[i]n 4
most cases a defendant who has shown that the district court 5
mistakenly deemed applicable an incorrect, higher [Sentencing] 6
Guidelines range has demonstrated a reasonable probability of a 7
different outcome” without a further showing of prejudice, because 8
the Guidelines calculation frequently is determinative of the sentence 9
the defendant receives. Molina‐Martinez v. United States, 136 S. Ct. 10
1338, 1346 (2016). That reasoning applies with even greater force 11
where, as here, the district court mistakenly found itself lacking any 12
discretion to impose a sentence other than a mandatory minimum life 13
sentence. 14
Moreover, while the lack of prejudice due to a procedural error 15
at sentencing may be apparent because, for example, a “detailed 16

-- 27 of 30 --

28
explanation of the reasons . . . make[s] it clear that the judge based the 1
sentence . . . on factors independent of” the error, this is not such a 2
case. Molina‐Martinez, 136 S. Ct. at 1346–47. Here, the court did not 3
discuss how it would have applied the Sentencing Guidelines or 4
balanced the 18 U.S.C. § 3553(a) factors had it not determined that a 5
life sentence was mandatory under § 3559(e). Rather, the court merely 6
stated (incorrectly) that it had “no authority” to impose less than a life 7
sentence. Joint App’x at 139. 8
Finally, the error seriously affected the fairness of the judicial 9
proceedings below. Instead of making an individualized 10
determination as to whether a life sentence was warranted, the district 11
court imposed a mandatory life sentence based on a statute that did 12
not apply. See Sanchez, 773 F.3d at 393–94 (finding that the district 13
court’s erroneous determination that a twenty‐year mandatory 14
minimum sentence applied seriously affected the fairness of judicial 15
proceedings); see also United States v. Folkes, 622 F.3d 152, 158 (2d Cir. 16

-- 28 of 30 --

29
2010) (per curiam) (finding that the district court’s use of a Guidelines 1
range more than twice the correct range seriously affected the fairness 2
of judicial proceedings). 3
* * * 4
Accordingly, vacating Kroll’s sentence is warranted to correct 5
the district court’s imposition of mandatory life sentences on Counts 6
One and Two. 7
In reaching that conclusion, we recognize that Kroll still faces a 8
Sentencing Guidelines range of decades in prison. In determining 9
what sentence is appropriate, the district court retains full discretion 10
to take account of all relevant factors, including the abhorrent 11
circumstances underlying the four counts of conviction in this case, 12
as well as those underlying the 1993 state‐court conviction. 13

-- 29 of 30 --

30
CONCLUSION 1
For the foregoing reasons, we VACATE the district court’s 2
sentence and REMAND the cause to the district court for proceedings 3
consistent with this opinion. 4

-- 30 of 30 --