According to the San Diego Union-Tribune, the agreement in him pleading guilty was he would receive a lighter prison sentence of 12 to 18 years. The announcement came just before he was set to be retried on charges relating to assaulting a third woman, which would have resulted in even harsher penalties.
Winslow has been in jail without bond since March following a string of sexually violent and inappropriate incidents.
Winslow was convicted on charges of raping a 58-year-old homeless woman back in May of 2018 after befriending her and getting coffee with her. He was then convicted of misdemeanor sexual misconduct charges after he exposed himself to another woman a few weeks after the rape in May of 2018.
Winslow II was facing nine years for rape, and misdemeanor, but the jury, in that case, remained deadlocked on several other charges. In the retrial, Winslow faced life if found guilty of raping that second woman.
Opposed to risking a life sentence, Winslow II decided to plead guilty to raping the teenager in 2003, and sexual battery of the 54-year-old in 2018 and will face 12 to 18 years in prison.
Prosecutors, in turn, agreed to drop kidnapping and rape charges in the hitchhiker case and one of two rape charges in the teenager case, according to the Union-Tribune. The woman who alleged she was raped at a San Diego party when she was passed out from drinking in 2003, when Winslow was 19 and she was 17, came forward after Winslow was arrested in 2018. He also agreed not to contest his prior convictions.
Kellen Winslow II is the son of Hall of Famer Kellen Winslow. Winslow II was drafted in 2004, with the 6th overall pick. That was the highest pick used on a tight end in over 30 years.
Winslow last played in the NFL in 2013 with the New York Jets. He is scheduled to be sentenced in February.