Winslow was the sixth pick in the 2004 NFL Draft after an excellent career at Miami where he was All-American in 2003. He played nine seasons in the NFL and made the Pro Bowl in 2007 when he caught 5 touchdowns and 1,106 yards for the Cleveland Browns.
In 2018, Winslow was arrested on kidnapping and rape charges. He was ordered by a judge to stand trial for the charges. In 2019, he was jailed after being arraigned for two new counts of lewd conduct and battery and willful cruelty to an elder. The trails were combined and are set to begin in May of 2019.