Ex-NFL Player Kellen Winslow II Pleads Guilty to Raping an Unconscious Teen

The plea deal came just hours before he was set to be retried on charges relating to assaulting three women.
November 5, 2019, 5:09pm
The plea deal came just hours before he was set to be retried on charges relating to assaulting three women.

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Kellen Winslow II, a former NFL tight end, pleaded guilty Monday to raping an unconscious teenager in 2003 and the sexual battery of a 54-year-old hitchhiker in 2018. The plea, part of an agreement he made with prosecutors to receive a lighter prison sentence of 12 to 18 years, came just hours before Winslow was set to be retried on charges relating to assaulting those two women and a third woman, with the potential for even harsher penalties, according to the San Diego Union-Tribune.


The 36-year-old from Encinitas, California, has been in jail without bail since March after a string of sexually violent or inappropriate incidents.

In June, Winslow was convicted on charges related to raping a 58-year-old homeless woman in May 2018 after he befriended her and convinced her to get coffee with him. He was also convicted of misdemeanor sexual misconduct charges after he exposed himself to a another woman a few weeks after that rape. He faced up to nine years in prison for those charges alone. However, the jury in that case remained deadlocked on several other charges, including the alleged rapes of the hitchhiker and the teenager — so the judge declared a mistrial. In the retrial, Winslow faced a potential life sentence if found guilty of raping the second woman.

So, rather than risk that life sentence, Winslow agreed to plead guilty to raping the teenager in 2003 and sexual battery of the 54-year-old woman in 2018. Prosecutors in turn agreed to drop kidnapping and rape charges in the hitchhiker case and one of two rape charges in the teenager case, according to the Union Tribune. (The woman who alleged she was raped at a San Diego party when she was passed out from drinking in 2003, when Winslow was 19 and she was 17, came forward after Winslow was arrested in 2018.) He also agreed not to contest his prior convictions.

In a bid for a lesser sentence of 12 years in prison, Winslow’s attorneys will claim he displays symptoms of a condition called chronic traumatic encephalopathy, or CTE, which cannot be diagnosed in living patients but has been linked to brain trauma from contact sports, according to USA Today. (There’s no evidence that the trauma causes criminal behavior.) Symptoms can include memory loss and impaired judgement from repeated blows to the head. Winslow was also accused of inappropriate behavior during his NFL career, including openly masturbating in front of teammates, according to a June Sports Illustrated profile. However, he was not accused of aggressive or criminal behavior during his career.

Winslow was a tight end for the NFL from 2004 to 2013. In 2004, he was the No. 6 overall draft pick — the highest-drafted tight end in more than 30 years, according to the Union-Tribune. He played for the Cleveland Browns, the Tampa Bay Buccaneers, the New England Patriots, and, finally, the New York Jets.

He’s scheduled to be sentenced in February.

Cover: Ex-NFL player Kellen Winslow II, standing, who was accused of committing several sex crimes against women in North County last year, including rape, answers a question from San Diego County Superior Court Vista Judge Blaine Bowman during a status hearing Friday, June 14, 2019 in Vista, Calif. (Howard Lipin/The San Diego Union-Tribune via AP, Pool)