Cleveland Browns: 6 Worst free agent contracts since 1999

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Cleveland Browns, Hue Jackson
Oct 28, 2018; Pittsburgh, PA, USA; Cleveland Browns head coach Hue Jackson looks on against the Pittsburgh Steelers during the fourth quarter at Heinz Field.The Steelers won 33-18. Mandatory Credit: Charles LeClaire-USA TODAY Sports /

The Cleveland Browns have had luck lately adding talent to their roster, but let’s not forget about these six guys that didn’t live up to expectations.

The Cleveland Browns appear to finally be under good upper management. Andrew Berry (General Manager, Paul DePodesta (Chief Strategy Officer), and Kevin Stefanski (Head Coach) have all done a fantastic job.

Yes, 2021 was a very disappointing 8-9 season, but that happens every once in a while. Cleveland fans need to remember all the 4-12, 5-11, and even and 0-16 seasons they suffered through not that long ago.

I get it, one taste of the playoffs and it’s hard to turn back. No one was more upset with the outcome of last year than me, but I still remain very optimistic that this organization is in good hands. That’s far more than I have ever thought in the last 23 years.

Remember, this is an organization that has had 12 head coaches since 1999 and what feels like100 starting quarterbacks. There are no doubt question marks on this roster, but for the first time since the Browns returned, they are getting good talent on this roster.

Guys like Denzel Ward, Nick Chubb, Myles Garrett, and even Baker Mayfield never existed in years past. There wasn’t enough talent on this team to win more than four games, let alone have someone who wanted to sign an extension

Cleveland was deemed a loser, the organization couldn’t draft, and it was impossible to draw in good free agents for so long.

Mistakes will still happen, but at a much lower rate than ever before. The list here is long, but here are six of the worse free agency deals the Cleveland Browns have made since their return in 1999.  I already know, I missed someone.