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Former NFL player Kellen Winslow II faces up to 18 years in prison after guilty plea on sex crime charges

Kellen Winslow II listens with attorneys
Kellen Winslow II listens with his attorneys Marc Carlos, left, and Gretchen von Helms, behind Winslow, during discussions before opening statements in the first day of his retrial in northern San Diego County on Monday.
(Charlie Neuman)

Moments before his rape retrial was to start Monday, former NFL player Kellen Winslow II pleaded guilty to two felonies, hesitating in court but eventually agreeing to a deal that caps his potential sentence at 18 years.

Winslow, 36, admitted to two counts involving two victims: the 2003 rape of an unconscious teen and the 2018 sexual battery of a 54-year-old hitchhiker in Encinitas.

Monday’s guilty pleas come five months after a jury found that he raped a 58-year-old homeless woman he had convinced to join him for coffee and also committed misdemeanor sexual misconduct involving two strangers.

With those convictions, the Encinitas resident was already facing nine years in prison. Further convictions at retrial could have sent him to prison with a life sentence. Now, with the plea deal, Winslow is looking at a total sentence between 12 and 18 years in prison.

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Even with the deal, Winslow faces lifetime registration as a sex offender and the possibility he will have to spend the rest of his life on parole. He now also has two strikes on his record.

Before going through with the change in plea, Winslow — son of a Chargers icon with the same name — hesitated several times during the hearing, often providing long pauses as Superior Court Judge Blaine Bowman asked him questions.

In court Monday afternoon, with the retrial jury waiting in the hallway, Bowman noted that Winslow had just spent roughly two hours discussing the change of plea with his attorneys and his family.

When Bowman asked the defendant if he had had enough time to make his decision, Winslow paused, then looked back in the courtroom at his father, who nodded.

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“I know you looked into the audience,” Bowman said to the defendant. “I’m asking you. I’m not asking anybody else. This is your decision and your decision alone.”

In accepting the guilty plea, Bowman warned Winslow to “be prepared” for any sentence between 12 and 18 years.

“I pray to God you give me 12 [years] so I can go home to my family as soon as possible,” Winslow said.

At one point, Winslow asked for more time to think about his decision, and Bowman gave him an additional five minutes. Later, when the judge went through some of the charges, Winslow was slow to respond.

“I’m sorry,” Winslow said. “I’m just not thinking very clearly right now.”

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The defendant is the son of former Chargers tight end and Hall of Famer Kellen Winslow. He grew up in San Diego and went to Patrick Henry and Scripps Ranch high schools before attending and playing football at the University of Miami.

In 2004, the younger Winslow was selected No. 6 overall by the Cleveland Browns in the NFL draft, the highest drafted tight end in more than 30 years. He reportedly earned more than $40 million over his NFL career.

After court, Winslow’s attorneys said they will supply the judge with reasons to consider imposing a sentence on the low end of the range, citing brain trauma brought on not just by football, but also a motorcycle crash several years ago.

Defense attorney Marc Carlos told reporters that his client suffers from frontal lobe damage, and cited the possibility that he has chronic traumatic encephalopathy, otherwise known as CTE, a degenerative brain disease linked to head trauma.

Chargers great Junior Seau, who killed himself in 2012, was found to have suffered from CTE.

Carlos and fellow defense attorney Gretchen von Helms acknowledged that CTE cannot be diagnosed without an autopsy. And while CTE could not be used as a defense in the case, the judge could consider brain trauma as a factor in Winslow’s sentencing.

In spring 2018, a few years after he left the league, Winslow II’s name landed in the headlines when he was arrested and accused of rape and other crimes, which authorities said targeted women in Encinitas.

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His first trial, held earlier this year, ended in June with a split verdict. A northern San Diego County jury found him guilty of the May 2018 rape of a 58-year-old Encinitas homeless woman he had befriended, exposing himself to a 57-year-old neighbor and lewd behavior in front of a 77-year-old woman in a Carlsbad gym.

Those convictions left Winslow facing up to nine years in prison.

But the jury deadlocked on several other charges, including two other alleged rapes. One of the accusers was a hitchhiker who said she got into a stranger’s SUV hoping for a ride down an Encinitas street on St. Patrick’s Day 2018. Instead, she said, she was driven behind a shopping center and raped.

The other deadlock arose from an incident several years earlier. That allegation involved a woman who last year reported that she had passed out after drinking at a San Diego house party and woke up being assaulted by Winslow in June 2003. She was 17 at the time. Winslow was 19 and by then a notable college football player.

Those two alleged assaults were at the heart of Winslow’s retrial. Had he been convicted, he would have faced life in prison.

The jury at the retrial was going to be told of Winslow’s convictions at the first trial.

In taking the plea deal, Winslow agreed not to challenge those convictions.

Prosecutors agreed to accept a plea to felony sexual battery and in exchange dropped kidnapping and rape charges involving the hitchhiker. They also dropped one of the two rape charges Winslow faced for the alleged 2003 encounter.

When his trial started earlier this year, Winslow had a total of five accusers. Between Monday’s guilty plea and the prior convictions at trial, Winslow was found to have committed wrongdoing against all five.

After the hearing, Deputy Dist. Atty. Dan Owens said his office felt that the potential for an 18-year sentence was “appropriate.”

“He has now been held accountable for conduct with all five sexual assault victims, and we have now doubled the potential exposure he is facing to 18 years,” Owens said.

Under state law, the district attorney’s office could consider asking a judge to designate Winslow as a sexually violent predator -- a designation that could keep him in custody indefinitely.


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