After his junior season, Winslow was selected as a First-Team All-American by the Associated Press. He also won the John Mackey Award as the nation's best collegiate tight end.
"Yeah, I don't give a hell. It's about this U, man. I don't give a flyin' you-know-what about a Vol. I don't give a damn! He would do the same thing to me. It's war. They don't give a freakin' you-know-what about you. They will kill you. They're out there to kill you. So I'm 'a kill 'em. You write that in the paper. You write that. You make money off that. No, man, I'm pissed. All y'all take this down. I'm pissed, man. We don't care about nobody except this U. We don't. If I didn't hurt him, he'd hurt me. They were gunnin' for my legs. I'm a come right back at 'em. I'm a fuckin' soldier!
Winslow took heavy criticism for the rant since many critics felt it was disrespectful to actual soldiers who were serving on duty in the Iraq War, which had started several months before. On November 10, 2003, Winslow issued a written apology for his comments, writing that: "I meant no disrespect to the men and women who have served, or are currently serving, in the Armed Forces. I cannot begin to imagine the magnitude of war or its consequences."
Somewhat surprisingly, Winslow was not the first University of Miami player selected in the 2004 Draft after draft day speculation that he could become the first tight end drafted number one overall. That honor went to the late Sean Taylor, who was chosen by the Washington Redskins one selection earlier, with the fifth overall selection.
Winslow would eventually choose sports agents Carl and Kevin Poston of Professional Sports Planning Inc. (PSP) to represent him at the negotiating table. The Poston brothers - whose clients at the time also included Orlando Pace and Charles Woodson - seemed an odd choice. Although respected in many circles for their ability to secure hefty contracts for their clients, the pair had developed difficult working relationships with several teams, league executives and the NFL Players' Association. In March 2006, Carl Poston was suspended for two years by the NFLPA disciplinary committee after admitting that he had not read the contract of Washington Redskins' linebacker LaVar Arrington, which did not include an agreed upon $6.5 million bonus. Arrington would later buy his way out of his Redskins contract to avoid arbitration in the matter. Eventually, the Postons secured a six-year $40 million deal for Winslow, including a $16.5 million signing bonus.
While Winslow was contractually obligated by the NFL's standard player contract not to "engage in … any activity other than football which may involve a significant risk of personal injury, and specifically not to ride a motorcycle under his contract with the Browns, he nevertheless purchased the powerful sport bike. Lt. Judy Neel of the Ohio State Highway Patrol reported that Winslow obtained a motorcycle learner's permit April 26, after initially failing a written exam administered in the Garfield Heights district of Cleveland. Initially, it was speculated that the Browns would seek to recoup a pro-rated share of the $6 million signing bonus Winslow received in 2004 and perhaps the entire $4.4 million option bonus he was paid in March 2005, although the Browns later declined to take such action.
In the opening game of the 2006 NFL season against the New Orleans Saints, Winslow recorded his first NFL touchdown, scoring on an 18-yard pass from quarterback Charlie Frye. Winslow emerged as a reliable target for Cleveland, finishing the year with 89 receptions, the most at his position on the season, which also tied Ozzie Newsome's all-time franchise record for receptions in a season.
Winslow became the cause of controversy in 2006. During a nationally-televised NFL Network game against the Pittsburgh Steelers on December 7, 2006, Winslow hit Steelers linebacker James Farrior from behind after a play, drawing criticism from outspoken former Pittsburgh linebacker Joey Porter, who called Winslow a "fag" twice during a post-game interview.
Winslow underwent microfracture surgery on his right knee January 31, 2007 at the Cleveland Clinic in an attempt to further repair cartilage damage sustained in the motorcycle accident in 2005.
On December 18, Winslow was named as a first alternate for the 2008 Pro Bowl On February 4, Antonio Gates of the San Diego Chargers announced he would not be attending the Pro Bowl due to injury. This paved the way for Winslow to make his first trip to the Pro Bowl.
He finished the season with 82 receptions for 1106 yards and five touchdowns.
During the 2008 campaign, Winslow was hospitalized for three days for an unknown illness.
| Pro. Career Off. Statistics | Receiving | |||||
| Year | Team | G | Rec | Yards | YAC | TD |
| 2004 | Cleveland | 2 | 5 | 50 | 10.0 | 0 |
| 2005 | Cleveland | 0 | 0 | 0 | - | 0 |
| 2006 | Cleveland | 16 | 89 | 875 | 9.8 | 3 |
| 2007 | Cleveland | 16 | 82 | 1,106 | 13.5 | 5 |
| Total | 34 | 176 | 2,031 | 11.5 | 8 | |