United States v. DeLaura, 2017 U.S. App. LEXIS 9884

DeLaura was charged with multiple child pornography and related sexual offenses and retained attorney Gary Greenwald; DeLaura’s mother arranged and paid the retainer.
The U.S. Attorney informed the district court of an allegation that Greenwald had a non‑platonic sexual relationship with DeLaura’s mother while representing DeLaura.
The court appointed independent conflict counsel (Stephen Lewis); Greenwald refused to confirm or deny the relationship and gave evasive answers at the inquiry/hearing.
Because Greenwald’s non‑cooperation prevented factual findings, the court instructed DeLaura to assume the worst‑case relationship and asked whether he would waive any resulting conflicts; DeLaura, after a confused colloquy, agreed to waive.
The district court accepted DeLaura’s guilty plea and sentenced him to 420 months (35 years); DeLaura later appealed arguing ineffective assistance due to the conflict and that the waiver was invalid.
The Second Circuit affirmed: the record had significant gaps about whether a relationship/conflict existed and whether prejudice occurred, so the court declined to decide ineffectiveness on direct appeal and indicated collateral review (habeas) and an evidentiary hearing would be the appropriate forum.

Issue	DeLaura’s Argument	Government’s Argument	Held
Whether defense counsel had a conflict of interest that rendered assistance ineffective	Greenwald’s alleged sexual relationship with DeLaura’s mother created an actual conflict impairing representation	Record is unclear whether any relationship/conflict existed or caused prejudice; any claim is better developed on collateral review	Court declined to resolve on direct appeal due to gaps; affirmed conviction and left ineffectiveness claim for habeas/evidentiary hearing
Whether DeLaura’s waiver of conflicts was knowing and intelligent	Waiver invalid because it was given under hypothetical assumptions without proper inquiry	Court complied with procedure given counsel’s refusal to answer; DeLaura had independent counsel and affirmed waiver	Court found waiver on the record but noted ambiguity and declined to adjudicate ineffectiveness on direct appeal
Whether procedural sentencing challenges to Guidelines calculation could be raised	DeLaura contends guideline calculation was erroneous	Plea agreement stipulated to Guidelines and included an appeal waiver for sentences below an agreed cap	Appeal waiver bars procedural Guidelines challenge; claim dismissed

United States v. Levy, 25 F.3d 146 (2d Cir. 1994) (district court duty to inquire when possible conflict is known)
United States v. Schwarz, 283 F.3d 76 (2d Cir. 2002) (some conflicts may be unwaivable)
United States v. Perez, 325 F.3d 115 (2d Cir. 2003) (definition of a "potential" conflict involves future divergence of interests)
Massaro v. United States, 538 U.S. 500 (U.S. 2003) (preference for resolving ineffective‑assistance claims on collateral review)
United States v. Adams, 768 F.3d 219 (2d Cir. 2014) (options on direct appeal for ineffective assistance claims)
United States v. Coston, 737 F.3d 235 (2d Cir. 2013) (enforceability of plea appeal waivers)