Eric Wayne Dempsey v. State of Iowa, 2015 Iowa Sup. LEXIS 26

In April 2008 Dempsey was arrested and charged with second-degree burglary (C felony), assault with intent to commit sexual abuse (initially charged as D felony then later as aggravated misdemeanor), and possession of burglar’s tools (aggravated misdemeanor). He had a prior 2003 conviction for third-degree sexual abuse.
Defense counsel sent multiple letters summarizing charges, possible penalties, and a plea offer history; some letters misstated maximum exposure by one year and mischaracterized one count’s severity.
The State’s first plea offer (June 27) would have dismissed burglary and required guilty pleas to two aggravated misdemeanors; the State would recommend incarceration. Counsel told Dempsey the concurrent maximum would be five years (actually four).
Dempsey declined the first offer, sought depositions. On the deposition day the State withdrew the first offer and presented a second, less favorable offer (plead to second-degree burglary (C felony) and an aggravated misdemeanor; sentencing enhancement and consecutive terms were noted). Faced with the risk of upgraded charges and mandatory enhancements, Dempsey accepted the second offer.
Dempsey later filed a postconviction-relief petition alleging ineffective assistance of counsel for failing to accurately inform him about the first plea offer’s terms and sentencing exposure. The district court denied relief (finding lack of prejudice); the court of appeals affirmed; the Iowa Supreme Court granted further review.

Issue	Dempsey’s Argument	State’s Argument	Held
Whether counsel rendered ineffective assistance in plea bargaining by misinforming Dempsey about the first plea offer’s terms and sentencing exposure, causing him to reject it and accept a worse later offer	Counsel misstated the plea terms (told him a felony rather than two misdemeanors) and sentencing exposure (off by a year), so Dempsey would have accepted the first, better offer if correctly informed	Even if counsel erred, Dempsey has not shown objective, corroborating evidence he would have accepted the first offer; he rejected it because he wanted to test whether witnesses would appear; therefore no prejudice	Court affirmed district court: possible deficiency, but no prejudice — Dempsey failed to show a reasonable probability he would have accepted the first offer or that the outcome would have been more favorable

Missouri v. Frye, 566 U.S. 134 (2012) (defendants have right to effective counsel during plea negotiations; prejudice requires showing defendant likely would have accepted earlier offer)
Lafler v. Cooper, 566 U.S. 156 (2012) (right to counsel extends to plea bargaining; remedy analysis for bad advice in plea context)
Padilla v. Kentucky, 559 U.S. 356 (2010) (counsel must give competent advice about deportation consequences of plea; principle that counsel must inform of clear consequences)
Hill v. Lockhart, 474 U.S. 52 (1985) (prejudice standard for ineffective-assistance claims in guilty-plea context)
Strickland v. Washington, 466 U.S. 668 (1984) (two-prong deficient performance and prejudice test for ineffective assistance)
State v. Clay, 824 N.W.2d 488 (Iowa 2012) (Iowa applies de novo review to ineffective-assistance claims and frames standard for plea-related claims)