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Top 15 worst free agent signings in NFL history

By Sayre Bedinger

Top 15 worst NFL free agent signings in history: Brock Osweiler #17 of the Houston Texans warms up on the field prior to the AFC Wild Card game against the Oakland Raiders at NRG Stadium on January 7, 2017 in Houston, Texas. (Photo by Bob Levey/Getty Images)
Top 15 worst NFL free agent signings in history: Brock Osweiler #17 of the Houston Texans warms up on the field prior to the AFC Wild Card game against the Oakland Raiders at NRG Stadium on January 7, 2017 in Houston, Texas. (Photo by Bob Levey/Getty Images) /
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NFL Free Agency can be an extremely valuable tool in building an elite roster. It can also serve as a cautionary tale for the greedy, get-rich-quick types of general managers. Some teams have been burned more than others in NFL free agency, but certain free agent signings in the last 30 or so years as the NFL has started giving out absolutely massive deals have been brutal.

More brutal than the rest.

What are the top 15 worst NFL free agent signings of all time?

15 worst NFL free agent signings in history

NFL free agent signings
Top 15 worst NFL free agent signings; Denver Broncos quarterback Case Keenum (4) scrambles with the ball in the first half against the Los Angeles Chargers at Broncos Stadium at Mile High. Mandatory Credit: Ron Chenoy-USA TODAY Sports /

15. Case Keenum, QB, Denver Broncos

The deal: 2 years, $36 million

Some of the moves on this list may not be on everyone’s list, but this is my list, and it’s hard to ignore how bad this move was by the Denver Broncos given the context of their situation. The Broncos had a top-five pick in the 2018 NFL Draft (5th overall). Their coaching staff, at the time, was tasked with coaching one of the rosters at the Senior Bowl, and they were gifted the opportunity to coach Baker Mayfield and Josh Allen the entire week.

Despite the up-close look at both Mayfield and Allen for a full week, the Broncos passed on drafting any quarterbacks at all. They didn’t make an aggressive enough push at Kirk Cousins (that we know of) in free agency and decided instead to go after Case Keenum of the Minnesota Vikings, fresh off the Minneapolis Miracle.

Keenum had a good season for the Vikings in 2017 in relief of Sam Bradford. Perhaps more important to the Broncos was Keenum’s connection to Gary Kubiak and Vance Joseph from their days together in Houston. Familiarity and connections are always key factors in free agency, sometimes to a fault.

The Broncos gave Keenum just a two-year deal, but it was a crippling move. They paid him starter money with $25 million guaranteed at signing. Keenum started just one season for the Broncos who finished as one of the 10 worst teams in the league in 2018. They traded him the following offseason to Washington and even with Russell Wilson on the roster today, the Broncos are still searching for the answer at QB.

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