Long since proven to be an all-time bust, the former tight end was convicted of rape, indecent exposure and lewd conduct in a San Diego courtroom on Monday.
The Jane Doe No. 2 Winslow was convicted of raping was a 58-year-old homeless woman at the time of the crime, according to Yahoo Sports.
The former first-round draft pick and onetime highest-paid National Football League tight end was arrested on the 2003 and 2018 charges at his Encinitas, California home in June 2018.
The North County jury, which has been deliberating since last week, reached verdicts on four of 12 counts filed against the one-time Pro Bowl player.
But a week later, authorities dropped a bomb with the announcement that they had rearrested Winslow, and were charging him with a string of sex crimes targeting women in their 50s or older, including two counts of forcible rape. Prosecutors say he felt empowered by his fame to abuse the most vulnerable.
While Winslow was out on bail and awaiting trial, a 77-year-old woman reported that he had committed lewd acts in front of her at a gym in February.
He was found not guilty of one count of another lewd act.
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Winslow's defense attorney, Marc Carlos, countered in his closing argument by urging the jurors to consider each alleged victim's case individually and not collectively under the notion that smoke means fire.
All five women testified in the case against Winslow, outlining their experiences with Winslow and the allegations they made.
A 57-year-old woman said he exposed himself to her while she tended to her garden in May of 2018.
A 54-year-old hitchhiker accused Winslow of raping her in his Hummer last year. The jury found him guilty of that charge Monday. A third woman came forward alleging that Winslow raped her while she was unconscious some 15 years ago.
Winslow II grew up in San Diego and attended Patrick Henry and Scripps Ranch high schools before heading to the University of Miami.
Deliberations are set to continue Tuesday.
The five women testified they didn't know about Winslow's career when they met him. The prosecution said the crux of their stories remained unchanged and that the case was supported by evidence that included traces of Winslow's DNA on one of the accuser's trousers and Global Positioning System locations that placed Winslow at locations where the accusers said the assaults occurred.