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.
Winslow also was found guilty on misdemeanor charges of indecent exposure and lewd conduct.
But a week later, authorities dropped a bomb when they announced 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.
Winslow, 35, faces life in prison if convicted of a dozen felony and misdemeanor counts.
The Cleveland Browns selected Winslow sixth overall in the 2004 draft; no Miami Hurricanes offensive playmaker has been drafted that high since.
In his National Football League career, Winslow caught 469 passes for 5,236 yards and 25 touchdowns.
Prosecutors say the son of Hall of Famer Kellen Winslow felt empowered by his fame to abuse the most vulnerable.
Winslow II played 12 games for the Jets in 2013. He was a one-time Pro Bowler, in 2007.
Winslow did not take the stand to defend himself during the nine-day trial.
All five women, including a homeless female, a hitchhiker and an immigrant who speaks limited English, testified during the trial that began May 20.
The homeless woman in Encinitas, who was 58 at the time, testified that he befriended her and attacked her next to his vehicle after inviting her for a coffee in May 2018. A 54-year-old hitchhiker accused Winslow of raping her in his Hummer last year.
The jury is expected to continue deliberations on the other eight charges, including an alleged rape of a homeless woman last year and of a 17-year-old girl in 2003, on Tuesday. Winslow's famous father attended every day of the trial.
"The jurors could benefit from an explanation as to what being under oath means", the note said.
Winslow's attorneys, Marc Carlos and Brian Watkins, told the jury that the charged incidents were either consensual sex or never occurred at all.
In opening statements on May 20, Winslow's attorneys said their married client had engaged in extramarital sex, including with the hitchhiker, who had Winslow's DNA in her trousers.
A 77-year-old woman who went to the same gym as Winslow in the beach community of Carlsbad said he committed lewd acts in front of her, including touching himself, while Winslow was free on $2 million bail in February. Bail was revoked following his arrest in that case.
Teri Figueroa reported this story from Vista, California, for the San Diego Union-Tribune.