United States v. Shawn P. Caldwell, 655 F. App'x 730

Caldwell was sentenced to 20 years for violating 18 U.S.C. § 2252A(a)(2) (possession of child pornography), an enhanced sentence under § 2252A(b)(1) because of a prior state conviction.
The § 2252A(b)(1) enhancement applies when 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.”
Caldwell’s prior conviction was an Iowa conviction under Iowa Code § 709.12 (1999) for indecent contact with a child (various acts of fondling, touching, solicitation).
Caldwell raised four challenges: (1) the phrase “relating to” is unconstitutionally vague; (2) his Iowa offense does not qualify as an offense “relating to” the listed sexual-abuse offenses; (3) a jury, not a judge, needed to decide whether the prior conviction qualified; and (4) his prior conviction was an Alford plea and thus cannot be used to enhance his federal sentence.
The Eleventh Circuit rejected all four arguments and affirmed the 20-year sentence.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Vagueness of “relating to” in § 2252A(b)(1)	“Relating to” is too indefinite; statute fails to give fair notice and invites arbitrary enforcement	The phrase can be read coherently; similar language was construed in Lockhart; not unconstitutionally vague	Statute is not unconstitutionally vague; Lockhart and precedent show coherent application
Whether Iowa § 709.12 conviction qualifies as a predicate	§ 709.12 (esp. subsections 3–4) does not match the federal listed offenses	The statute’s subsections (direct contact and solicitation) all relate to sexual abuse of a minor; precedents treat solicitations as qualifying	The Iowa conviction qualifies under § 2252A(b)(1); all subsections relate to sexual abuse of a minor
Need for jury finding that the prior conviction “relates to” listed offenses	A jury must decide any fact that increases punishment	Prior-conviction fact can be found by judge; identifying qualifying prior is a legal question	No jury determination required; judge may determine that the prior conviction qualifies
Use of an Alford plea as a predicate conviction	An Alford plea should not be used to enhance sentence because defendant did not admit guilt	Alford pleas are treated as guilty pleas for collateral sentencing purposes under binding precedent	An Alford plea qualifies; precedent treats Alford pleas as valid predicates

Lockhart v. United States, 136 S. Ct. 958 (2016) (construed identical § 2252(b)(1) language and found coherent meaning)
Johnson v. United States, 135 S. Ct. 2551 (2015) (vagueness doctrine principles for sentencing provisions)
Lanier v. United States, 520 U.S. 259 (1997) (rule of lenity explained)
Taylor v. United States, 495 U.S. 575 (1990) (categorical approach to prior convictions)
Descamps v. United States, 133 S. Ct. 2276 (2013) (divisibility and categorical approach)
Bifulco v. United States, 447 U.S. 381 (1980) (lenity applies to penalties)
Alleyne v. United States, 133 S. Ct. 2151 (2013) (judges may find prior-conviction facts affecting sentence)
United States v. Ramirez-Gonzalez, 755 F.3d 1267 (11th Cir. 2014) (Alford pleas treated as guilty pleas for sentencing)
United States v. McGarity, 669 F.3d 1218 (11th Cir. 2012) (broad reading of “relating to” covers solicitation-style offenses)
United States v. Ramirez-Garcia, 646 F.3d 778 (11th Cir. 2011) (sexual abuse of a minor includes nonphysical and solicitational conduct)