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Kellen Winslow II pleads guilty to raping unconscious woman ahead of retrial

Former NFL tight end avoids life sentence

November 4, 2019

Former NFL player Kellen Winslow Jr. pleaded guilty Monday to raping an unconscious teen in 2003 and to sexual battery involving a 54-year-old hitchhiker in a deal that spared him the possibility of life in prison.

Winslow initially hesitated and seemed to agonize over his decision.

"I'm sorry. I'm just not thinking very clearly," Winslow told the judge at one point.

He asked the judge for more time before he finally entered the guilty pleas moments before he was about to be retried on six felonies including kidnapping, sodomy, forced oral copulation and two charges of rape in San Diego County Superior Court that could have sent him to prison for life if he was convicted.

In exchange for his plea, the court agreed to sentence him to between 12 and 18 years in prison for the two charges and dismiss the others.

In June, a jury found him guilty of raping a homeless woman in Encinitas, north of San Diego. Jurors also convicted him of two misdemeanors -- indecent exposure and a lewd act in public -- involving two other women.

But that jury failed to agree on other charges, including the alleged rape of the hitchhiker and the rape of the unconscious 17-year-old girl in 2003 when he was 19. Under the plea deal, the attack on the hitchhiker was reduced to sexual battery.

The 36-year-old former tight end -- at one point one of the highest-paid in the NFL -- had previously pleaded not guilty to the charges. His attorney, Gretchen von Helms, had said the sex was consensual.

Five women took the witness stand this summer, and three of them were expected to testify again.

Prosecutor Dan Owens said outside of the courtroom that the women were brave to want to testify again but that he was glad they would not have to put themselves through that again.

"Each of these victims, they didn't try to come out here in order to try to frame Mr. Winslow," Owens said "The fact that they had that courage to come forward and speak with law enforcement and to testify to all the things that he had done while facing all these cameras, I think it was important to me to make sure that that truth was heard, and it was important to me to make sure that he was held accountable for each one of those crimes."

Defense attorney Marc Carlos said Winslow made a difficult choice to accept the plea deal.

"The downside of any conviction would land him in prison for the rest of his life, and he made this decision based upon his family, his father, his children, and he wanted to be there for them in the future," Carlos said.

Defense attorneys attacked the credibility of the five women and pointed out inconsistencies in their stories in the first trial.

The court had planned to allow the new jury to hear that Winslow was convicted of raping the homeless woman, who would have been among those testifying again.

Jurors would also have been told about the indecent exposure conviction, though that woman was not expected to take the stand.

Winslow, who played for Cleveland, Tampa Bay, New England and the New York Jets, earned more than $40 million over 10 seasons in the NFL. He is the son of Chargers Hall of Fame receiver Kellen Winslow, who was in the courtroom throughout the first trial and on Monday.

Winslow Jr. repeatedly looked back at his father before entering his plea. As he left the courtroom Monday, he reached an arm out to his father, who responded by touching his fist to his heart.

Winslow's attorneys said he suffers from traumatic brain injury from his football playing and a motorcycle accident that ended his career.

They will argue that information should be taken into consideration at his sentencing hearing.

Courtroom outburst from Winslow Sr.

Winslow’s father Kellen Winslow Sr. — an NFL Hall of Fame tight end and San Diego Chargers icon — confronted San Diego County Deputy Prosecutor Dan Owens, telling him “Do not look over here” in the courtroom.

A bailiff then removed Winslow Sr. from the courtroom.

Plea deal follows June conviction on another rape charge

Jurors convicted Winslow in June of raping a 58-year-old homeless woman in 2018, but were deadlocked on six additional felonies, prompting the scheduled retrial. Winslow originally faced 12 charges, seven of them felonies.

The jury in June also found Winslow guilty of a misdemeanor indecent exposure charge involving a 58-year-old neighbor and lewd conduct with a 78-year-old woman in a health club.

The prospect of facing life in prison prompted Winslow to reach Monday’s plea deal before the retrial commenced. Prosecutors dropped the remaining charges that could have resulted in a longer sentence as part of the plea agreement.

The deal came at the last minute as jurors had already been seated to hear testimony.