From San Diego, California, Winslow Jr. is the son of Hall of Fame TE Kellen Winslow. After a potent High School career, Winslow Jr. committed to play collegiately at the University of Miami.
He proceeded to dominate as a Hurricane, earning a starting role as a sophomore following Jeremy Shockey going pro. As a sophomore, Winslow set University of Miami records for a TE with 57 receptions for 726 yards and 8 touchdowns, and was named a 1st-team All-American and a finalist for the Mackey Award. He followed up this dominant effort with a strong junior campaign, this time winning the Mackey Award and receiving 1st-team All-American honors. He declared for the NFL draft following his junior season.
Winslow was drafted 6th overall in the 1st round by the Cleveland Browns. His finest season in the NFL came in 2007, when he recorded 82 receptions for 1,106 yards and 5 touchdowns, and was selected to the Pro Bowl. Winslow was traded to the Tampa Bay Buccaneers in 2010, where he set single-season franchise records for receptions by a TE. He also had stints with the Seattle Seahawks, New York Jets, and New England Patriots.
In 2017, Winslow joined The Spring League to attempt a comeback after sitting out for 2 seasons. The league gave him an ideal platform to get live repetitions and film in real-time against elite competition.