The plea deal was made in San Diego Superior Court after five accusers had come forward stating that Winslow had raped them. This past June, Winslow was convicted of four criminal charges, including raping a homeless woman and committing a lewd act in public, but a jury deadlocked on eight others.
On Monday, Winslow was due back in court to be retried on those eight counts, but instead he struck up a deal to plead guilty to the two counts mentioned at the top of this page, in order to get the other six charges dropped. That is significant because, if found guilty on those counts, Winslow could've been sentenced to life in prison.
Now he will face between 12-18 years in prison, with that sentence to be determined during a court appearance on February 19, 2020.
TMZ reports that Monday's guilty pleas were for crimes that occurred in 2003 and 2018. The first of those is said to have occurred at a party when a then 19-year-old Winslow Jr. allegedly raped an unconscious 17-year-old identified as Jane Doe #4.
As for the 2018 incident, that involved a 54-year-old woman identified as Jane Doe #1, who says that Winslow raped her in his Jeep.
Winslow had previously proclaimed his innocence to the charges prior to Monday's guilty plea. TMZ reports that Winslow asked the judge for a minimum sentence of 12 years so that he could see his family.
Also in attendance at Monday's proceedings was Winslow's father, Hall of Famer Kellen Winslow Sr., who was reportedly emotional, with him telling the prosecutor at one point "Do not look over here."
Winslow Jr. played 10 seasons in the NFL, from 2004 to 2013, after being taken in the first round of the '04 Draft out of Miami with the sixth overall pick. During his career he made one Pro-Bowl, and played with the Browns, Bucs, Patriots (for a game), and Jets.