Castelle v. United States, 1:21-cv-04694

May 2019 superseding indictment charged Eugene Castelle with illegal gambling (Count One), attempted extortion (Count Two), and racketeering conspiracy (Count Three).
Government offered a plea: plead to Count One only (illegal gambling); Counts Two and Three would be dismissed; estimated Guidelines range 8–14 months.
Trial counsel Gerald McMahon advised Castelle of risks and gave an estimate (33–41 months if convicted on Counts One and Three); Castelle rejected the plea and elected trial.
Jury convicted Castelle of illegal gambling and racketeering, acquitted on attempted extortion; at sentencing the court found uncharged extortion by a preponderance, computed Guidelines 53–61 months, and imposed a 77-month sentence.
Castelle filed a §2255 petition claiming ineffective assistance for incorrect Guidelines advice that caused him to reject the plea, and separately sought release on bond pending §2255.
The district court denied the §2255 petition and the bond motion, finding counsel’s performance reasonable and petitioner failed to show Strickland prejudice; no evidentiary hearing was required.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether counsel rendered ineffective assistance by miscalculating or misadvising about the likely Guidelines/sentence tied to the plea	McCann (Castelle) argues counsel gave a lower Guidelines assessment and that, but for this, he would have accepted the plea	McMahon reasonably based estimates on charged counts, warned of higher outcomes, urged plea acceptance; estimates are inherently uncertain	Counsel’s performance was reasonable; no Strickland deficiency found
Whether Castelle established Strickland prejudice — reasonable probability he would have accepted plea and received lesser punishment	Castelle says he would have accepted the government’s plea and received a lower sentence	No contemporaneous corroboration that he would have accepted; plea might not have remained; defendant gambled by going to trial	Prejudice not established; no reasonable probability plea would have resulted in less prison time
Whether petitioner should be released on bond pending resolution of §2255	Requests release on bond while §2255 is decided	Petition lacks merit; no basis for release	Bond denied

Strickland v. Washington, 466 U.S. 668 (1984) (two‑prong standard for ineffective assistance of counsel)
Missouri v. Frye, 566 U.S. 134 (2012) (defendant has right to counsel’s effective advice about plea offers)
Lafler v. Cooper, 566 U.S. 156 (2012) (prejudice analysis in plea‑related ineffective assistance claims)
Purdy v. United States, 208 F.3d 41 (2d Cir. 2000) (counsel should discuss strengths/weaknesses and likely sentencing outcomes when advising on pleas)
Doe v. United States, 915 F.3d 905 (2d Cir. 2019) (look to contemporaneous evidence to substantiate whether defendant would have accepted a plea)
Cuoco v. United States, 208 F.3d 27 (2d Cir. 2000) (standards for §2255 relief)
Puglisi v. United States, 586 F.3d 209 (2d Cir. 2009) (no evidentiary hearing where the record conclusively shows no relief)
Chang v. United States, 250 F.3d 79 (2d Cir. 2001) (affidavits may expand the record without a full hearing)
Frady v. United States, 456 U.S. 152 (1982) (collateral review burden is higher than on direct appeal)