At the time, a jury also found him guilty on two misdemeanor charges and acquitted him of another, but it deadlocked on some charges, leading to the retrial.
Winslow pleaded guilty Monday to the rape of an unconscious teenager in 2003 and the sexual battery of a 54-year-old woman in 2018. Other pending charges that were dismissed as part of the deal.
If the retrial had gone forward, Winslow risked a life sentence.
The plea deal also required Winslow not to contest the previous verdicts (per the San Diego Union-Tribune). Those included a misdemeanor conviction for lewd conduct, in a case involving a 77-year-old woman at a gym in Carlsbad, Calif., and one for indecent exposure, involving a 57-year-old woman.
Per multiple reports, Winslow was hesitant to accept the deal in court, requiring a recess of several minutes to confer with his attorneys before he declared that he would waive his right to a jury trial.
Winslow also repeatedly looked back at his father, Kellen Winslow Sr., a Pro Football Hall of Fame tight end who was a longtime member of the San Diego Chargers.
At the outset of the proceedings, according to USA Today, Kellen Winslow Sr. raised his voice and told San Diego County prosecutor Dan Owens, “Do not look over here.” The 62-year-old, who was a fixture at his son’s first trial, was then led out of the courtroom by a bailiff.
“The downside of any conviction would land him in prison for the rest of his life,” an attorney for Winslow, Marc Carlos, said Monday (via USA Today). “He made the decision based on his family, his father, his children, and he wanted to be there for them in the future. So by accepting a plea agreement with the sentencing range that he has, he’s got a set number he has to get to rather than spending the rest of his life in prison.”
After Kellen Winslow II was arrested in 2018, a woman came forward and said he had raped her at a San Diego-area party in 2003, when she was 17 and he was 19. She was expected to testify in the retrial.
“I think the first trial was a dose of reality,” said a San Diego-based criminal defense attorney, David P. Shapiro, who has watched the case closely but is not connected to the matter. In a phone interview with The Post, Shapiro said Winslow, who pleaded not guilty on all counts in June, looked “completely shocked and stunned” when the guilty verdicts were announced.
Shapiro said that a possible motivating factor for Winslow in abruptly agreeing to a deal Monday was “realizing that he could get eight years just on that count [of rape], and in all likelihood was going to get close to nine years anyway, no matter what happened in this case."
Carlos, the defense attorney, claimed Monday that Winslow suffers from frontal lobe damage, and he said that at sentencing he would raise the possibility that his client suffers from chronic traumatic encephalopathy, which is commonly known as CTE, a neurodegenerative disease that has been linked to the kinds of concussive and subconcussive impacts football players frequently incur. CTE can’t be diagnosed in living patients.
The No. 6 overall pick in the 2004 draft, Winslow spent 10 years in the NFL, playing for the Cleveland Browns, Tampa Bay Buccaneers, New England Patriots and New York Jets.
Shapiro predicted that CTE “will be used pretty heavily by the defense as it relates to mitigation” of Winslow’s sentence, but he also saw a double-edged sword. The possibility that Winslow suffers from an as-yet incurable disease that can, among other things, impair impulse control could be an issue when he comes up for parole, as authorities could cite California’s Sexually Violent Predators law in seeking to commit him for an indefinite, additional period if he is deemed to still be a “danger to the community.”
“I’m satisfied that now Mr. Winslow has been held accountable for his conduct involving five separate victims over the course of 15 years,” Owens, the prosecutor, said Monday. “I was told this morning that they had worked hard over the weekend to discuss with Mr. Winslow the parameters of a potential change in plea, and it was not until this morning that they offered the specific resolution that ultimately we agreed to.”
Winslow is scheduled to be sentenced in February.