According to the AP, some of the 37-year-old's crimes included raping a homeless woman in 2018, picking up a hitchhiker and raping her, performing a lewd act in front of a 77-year-old woman at the gym, and attacking a teenager who was passed out at a party. He also exposed himself to a 57-year-old neighbor who was gardening.
Winslow was convicted of forcible rape, rape of an unconscious person, assault with intent to commit rape, indecent exposure, and lewd conduct in public. His prison term was part of a plea deal and was the maximum sentence allowed.
Winslow's father Kellen Winslow was a Hall of Fame tight end for the San Diego Chargers. Winslow II was also a tight end and played for the Cleveland Browns, Tampa Bay Buccaneers, New England Patriots, and New York Jets. He was, at one time, the highest-paid tight end in the NFL.
In 2019, a jury found Winslow guilty of forcible rape, indecent exposure, and a lewd act in public. He reportedly pleaded guilty to raping the teen at the party and sexual battery of the hitchhiker.
According to the Union-Tribune, Winslow's attorney Marc Carlos said Winslow suffered from head trauma he sustained while playing football, calling CTE (chronic traumatic encephalopathy) the "elephant in the room."
Winslow said at the sentencing hearing, "In the future, I do plan to tell my story."