Kaplan v. United States, 663 F. App'x 69

Leonid Kaplan pled guilty to one count of conspiracy to commit health-care fraud and mail fraud and received a 94-month sentence; restitution and forfeiture were set at $2,353,427 and three years supervised release was imposed.
Kaplan’s plea agreement included an appellate/collateral-attack waiver for any sentence at or below 97 months and stipulated to the loss/restitution amounts; he also agreed to withdraw pending insurance claims worth hundreds of thousands of dollars.
Kaplan filed a 28 U.S.C. § 2255 motion arguing ineffective assistance of counsel: his lawyer failed to advise him that U.S.S.G. § 2X1.1(b)(2) might afford a three-level reduction for conspiracies.
The district court denied relief; Kaplan appealed and this Court granted a certificate of appealability on waiver enforceability and counsel’s failure to advise about § 2X1.1(b)(2).
The Sentencing Guidelines at issue direct that conspiracy offense levels are generally calculated under § 2X1.1, which can reduce the offense level by three in appropriate circumstances and refers to § 2B1.1 for loss-based adjustments.

Issue	Kaplan's Argument	United States' Argument	Held
Whether plea waiver bars collateral attack	Waiver ineffective as to his § 2255 claim	Waiver is enforceable and bars collateral attack up to 97 months	Court assumed waiver might not bar appeal but resolved merits against Kaplan
Whether counsel was ineffective for not advising re: § 2X1.1(b)(2)	Counsel should have advised Kaplan that conspiracy reduction might apply, lowering his offense level by three	Counsel reasonably believed reduction did not apply because Kaplan completed the acts and losses exceeded $2.5M	Counsel’s performance not shown deficient; alternative holding: no prejudice under Strickland
Applicability of § 2X1.1(b)(2) three‑level reduction	Kaplan argues reduction applies despite completed acts	Government: reduction inapplicable when necessary acts were completed or nearly completed	Reduction did not apply because Kaplan (or co-conspirators) had completed or were about to complete acts yielding >$2.5M loss
Effect of Application Note 4 to § 2X1.1	Kaplan contends Note 4 might yield lower level	Government: Note 4 yields the greater of two offense levels and would not lower below level 18	Note 4 does not produce a lower offense level; level 18 stands

Strickland v. Washington, 466 U.S. 668 (ineffective assistance standard: deficient performance and prejudice)
Scanio v. United States, 37 F.3d 858 (standard of review on § 2255 appeal: facts for clear error, law de novo)
Chrysler v. Guiney, 806 F.3d 104 (application of Strickland in the Second Circuit)