Skakel v. Commissioner of Correction, SC19251

Petitioner Michael Skakel was represented at trial by attorney Michael Sherman; habeas court found ineffective assistance of counsel and ordered a new trial.
The appellate opinion is a concurrence/dissent by Justice Robinson addressing two alleged failures by Sherman: (1) choosing to pursue a third-party culpability defense targeting Kenneth Littleton instead of Thomas Skakel, and (2) failing to locate and interview Denis Ossorio, a potential disinterested alibi witness for the night of Martha Moxley’s murder.
Robinson agrees with the majority that Sherman’s decision to focus on Littleton rather than Thomas was a reasonable strategic choice entitled to deference under Strickland.
Robinson departs from the majority on the Ossorio issue: she agrees with Justice Palmer that Sherman’s failure to attempt to contact Ossorio was objectively unreasonable and prejudicial under Strickland.
Sherman testified he knew of Ossorio but did not try to contact him, based on assumptions that Ossorio would not recall events from 20+ years earlier and that Ossorio, like Dowdle, had been separated and would have no helpful observation.
Robinson would affirm the habeas court’s grant of a new trial because the failure to investigate Ossorio was deficient performance and likely changed the outcome (reasonable probability of a different result).

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether counsel was ineffective for pursuing Littleton as third-party culprit instead of Thomas Skakel	Sherman unreasonably failed to implicate Thomas, weakening third-party defense	Sherman reasonably chose Littleton based on strategic assessment and risk of implicating Thomas	Counsel’s decision to pursue Littleton was a reasonable strategic choice; not ineffective under Strickland
Whether counsel was ineffective for not locating/interviewing Denis Ossorio (alibi witness)	Failure to attempt contact was unreasonable and deprived Skakel of critical, disinterested alibi evidence	Sherman reasonably assumed Ossorio would not recall events and thus did not pursue contact	Failure to investigate Ossorio was objectively unreasonable and prejudicial; warrants new trial, per Robinson

Strickland v. Washington, 466 U.S. 668 (1984) (two-part standard for ineffective assistance: deficient performance and prejudice)
Washington v. Meachum, 238 Conn. 692 (1996) (right to effective — not perfect — counsel; deference to strategic decisions)