O'Reagan v. Commissioner of Correction, AC44390

O’Neil O’Reagan pleaded guilty (2008) to burglary in the second degree, conspiracy to commit robbery in the second degree, and sale of a narcotic substance; sentences were imposed to run concurrently (burglary: 10 years, execution suspended after 4 years + probation; robbery: 3 years; narcotics: 1 year).
In 2017 he was taken into federal immigration custody; by that time the robbery and narcotics sentences had expired, but the burglary sentence remained active because of a pending violation of probation.
O’Reagan filed a habeas petition (Dec. 2017) alleging (inter alia) ineffective assistance of trial counsel for failing to investigate/advise about the case and for failing to advise about immigration (deportation) consequences of his pleas.
The Commissioner moved to dismiss portions of the petition for lack of jurisdiction; Judge Newson dismissed the claims tied to the robbery and narcotics convictions because those sentences had fully expired before the habeas filing; the burglary-related claims proceeded to trial.
After trial the habeas court (Judge Bhatt) denied relief as to the remaining claims, finding counsel’s investigation and plea advice reasonable and concluding Padilla-based immigration advice was not constitutionally required at the time of the plea; judgment affirmed on appeal.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether habeas court had jurisdiction over robbery and narcotics convictions whose sentences expired before filing	Aggregate/global plea/aggregate package theory: custody on burglary is enough to confer jurisdiction over the whole plea package	Sentences for robbery and narcotics expired prior to filing; concurrent sentences do not create a continuous stream of custody; aggregate package does not expand habeas jurisdiction	Court held no jurisdiction over expired concurrent sentences; dismissal affirmed
Whether trial counsel rendered ineffective assistance by failing to investigate and advise about strengths/defenses	Counsel failed to investigate potential witnesses/defenses and misadvised about likelihood of trial success	Counsel reviewed discovery, assessed case as strong, advised petitioner of risks and likely sentence if convicted at trial; petitioner gave no leads or witnesses	Court held counsel’s performance was within reasonable competence; claim denied
Whether counsel was ineffective for failing to advise about immigration consequences of plea	Counsel failed to warn of deportation risk; had he known, he would not have pleaded guilty	Padilla rule (duty to advise re deportation) did not apply retroactively; at plea time no constitutional duty under federal or Connecticut law	Court held Padilla did not apply retroactively (Chaidez, Thiersaint); no constitutional duty then; claim denied

Padilla v. Kentucky, 559 U.S. 356 (2010) (counsel must advise noncitizen client about deportation consequences of a plea)
Chaidez v. United States, 568 U.S. 342 (2013) (Padilla announced a new rule and does not apply retroactively)
Thiersaint v. Commissioner of Correction, 316 Conn. 89 (2015) (Connecticut Supreme Court: Padilla not retroactive under state law)
Lebron v. Commissioner of Correction, 274 Conn. 507 (2004) (conviction whose sentence expired before filing is not "in custody" for habeas jurisdiction)
Foote v. Commissioner of Correction, 170 Conn. App. 747 (2017) (consecutive sentences create a continuous stream for habeas jurisdiction; concurrent sentences do not)
State v. Miranda, 274 Conn. 727 (2005) (aggregate package theory: vacatur of a multi-conviction sentence requires resentencing constrained by original sentencing intent)
Strickland v. Washington, 466 U.S. 668 (1984) (two-prong test for ineffective assistance of counsel)
Hill v. Lockhart, 474 U.S. 52 (1985) (application of Strickland prejudice standard to guilty-plea challenges)