Ranking Cleveland Browns 5 worst first round draft picks since 1999

Every team misses on draft picks, but unfortunately for the Cleveland Browns, it has been a rough few decades when they tried to find talent. 

It’s well known that the Cleveland Browns have had loads of trouble hitting on draft picks since their return to the league in 1999.

With a constant change in the coaching staff and front office every few years, it seemed like no one could ever get on the same page. In recent years, Cleveland has been in good hands with Andrew Berry and John Dorsey.

Berry more so than Dorsey, but we have to thank Dorsey for players such as Denzel Ward and Nick Chubb. Before them, it was a rotating door at general manager, and the misses on draft picks show that. Let’s take a look at the worst draft picks since the team’s return in 1999.

Cleveland Browns worst pick No. 5: TE Kellen Winslow Jr – taken 6th overall in 2004

Things really didn’t get off to a great start for Kellen Winslow, Jr. after he was selected in the 2004 draft. In his rookie year, he suffered a broken leg and played only two games.

In 2005, he was expected to make a comeback until he got in a motorcycle accident and tore his ACL. He was charged with disregarding safety and missed the entire 2005 season.

He did have a decent comeback in 2006 and 2007, catches 89 and 82 passes in those years, but when you take a guy 6th overall in the draft, he is expected to play for your team for a decade or more and notch multiple Pro Bowls and All-Pros.

Winslow fell way short of those expectations and was only on the Browns until 2008. It’s even more troubling that years later, he was sentenced to 14 years in jail for sex crimes against several women. Not a great character selection by the front office at the time either.