Kellen Winslow II Has Officially Agreed to a Lengthy Prison Sentence for His Sex Crimes

Former Cleveland Browns tight end Kellen Winslow II had the potential to become one of the league’s top players at his position.

Injuries and maturity issues got in Winslow’s way during his nine NFL seasons. Now, the ex-Pro Bowl selection is headed to prison after taking a plea deal for multiple sex crimes.

Kellen Winslow II is headed to prison

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Nearly a decade after his final NFL game, Kellen Winslow II is preparing to spend many years in prison.

Winslow, a first-round selection of the Cleveland Browns in 2004, agreed to a new plea deal in San Diego Superior Court. The plea deal sentenced Winslow, 37, to 14 years in prison for multiple sex crimes. 

According to USA Today, Winslow raped two women, assaulted another, and committed misdemeanor sex crimes against two others. Winslow previously agreed to a plea deal in November 2019 after pleading guilty to rape and sexual battery charges. 

The 2019 plea deal stipulated a sentencing range of 12 to 18 years in prison, but would not have sentenced Winslow to life behind bars. 

Winslow, who is Black, brought up his background before the hearing adjourned.

“I just wanted to know if I was to go to trial would I get an actual jury of my peers that (are) people of color that would look like me? Would I get jury trial like that?”

Judge Blaine Bowman told Winslow that race “was not at issue” in the hearing. After a short recess, Winslow agreed to the plea deal.

Winslow’s sentencing hearing is currently scheduled for March 3.

Winslow II had various issues throughout his NFL career

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Before ever going on trial, Kellen Winslow II already had a rap sheet and a reputation for trouble.

Winslow famously missed all of the 2005 season following a motorcycle accident. The second-year tight end tore his right ACL and later battled a staph infection for six weeks. 

When Winslow suffered another staph infection in 2008, he criticized the Browns for not fixing the problem. Cleveland suspended Winslow for a week before rescinding that decision. 

While with the New York Jets in 2013, Winslow served a four-game suspension for using performance-enhancing drugs.

According to, police arrested Winslow in East Hanover (N.J) during the 2013 season for possession of synthetic marijuana. Police were called to the scene outside a Target because a woman thought she saw Winslow masturbating in his vehicle.

Kellen Winslow II and his father both played in the NFL

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There once was a time where Kellen Winslow II was among the NFL’s top tight ends.

In nine NFL seasons, Winslow turned 469 receptions into 5,236 yards and 25 touchdowns. Winslow was at his best with the Tampa Bay Buccaneers, hauling in 218 catches for 2,377 yards and 12 touchdowns from 2009-11.

A Pro Bowl selection in 2007 with the Browns, Winslow also played for the New England Patriots and New York Jets.

Winslow’s father, Kellen Sr., had a much better NFL career. In nine NFL seasons, the elder Winslow hauled in 541 catches for 6,741 yards and 45 touchdowns.

Winslow Sr. also caught four touchdowns in six postseason games.

A five-time Pro Bowl and three-time first-team All-Pro selection, Winslow Sr. entered the Pro Football Hall of Fame in 1995. The NFL named Winslow to its 100th Anniversary All-Time Team in 2019.

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