Worst NFL Free Agency Signings Of All Time

March 16, 2026

Dominick takes a look back at the worst NFL free agency signings of all time. Which players were the worst free-agent acquisitions made in NFL history?

With the 2026 free agency period open in the NFL, it is time to look back at some of the major mistakes that have been made in years past.

While many teams will improve through their acquisitions, many others will continue their slide into obscurity.

Whether it be through bad coaching, bad ownership, team curses, or injury, several factors can play a role in disappointing results. So, let's look at the worst of the worst free-agent signings.

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Randy Gregory, Denver Broncos (5 years, $70 million, 2022)

This was a rare time when the Dallas Cowboys got out of a bad deal.

After Gregory found language in the Cowboys' proposed contract, he decided to sign with the Denver Broncos for the same contract. Denver felt that it was getting a steal when, in fact, Gregory would be the one stealing.

After the signing during the 2022 offseason, Gregory played in four games before suffering a knee injury, which kept him sidelined until Week 15. After a regime change, Sean Payton was brought in to clear house and turn over the roster.

After three games in the 2023 season, he saw the first problem that had to go was Gregory. After sitting him out for multiple games, Payton was finally able to ship Gregory off to the San Francisco 49ers. After playing just 10 games for the Broncos, his tenure was over.

Statement from Broncos’ OLB Randy Gregory, who is appealing the one-game suspension that the NFL handed down Monday: pic.twitter.com/AYWp8ccHud

— Adam Schefter (@AdamSchefter) December 27, 2022

Nnamdi Asomugha, Philadelphia Eagles (5 years, $60 million, 2011)

After being drafted by the Oakland Raiders in 2003, Asomugha became one of the best cornerbacks in the NFL. Mainly playing in press coverage, Asomugha had two first-team All-Pro selections.

His second selection came in the year of his impending free agency. This made him a hot commodity, and the Eagles splurged for him during an offseason in which the team accrued the Dream Team. Thanks, Vince Young.

Much like the rest of the team that season, Asomugha floundered in a scheme not made for him.

Juan Castillo, the worst selection for defensive coordinator that Andy Reid could have made, tried having Asomugha play in a zone, something he was not comfortable with or did well. Not to mention, at the age of 30, Asomugha was also losing his foot speed, leading to getting burned in the same bad scheme.

Had Asomugha gone to a team that did not have an offensive line coach as its defensive coordinator, he could have worked out great. Unfortunately, in what was an unwinnable situation, he suffered the most and continues to be looked at in a bad light due to the contract terms.

Brock Osweiler, Houston Texans (4 years, $72 million, 2016)

Osweiler must pray every night to Peyton Manning for this contract. In the 2015 season, in which the Denver Broncos won the Super Bowl, it was Osweiler, not Manning, who got them there.

Osweiler was forced to play in five of the seven games leading up to the Super Bowl, and he was able to make the plays needed to continue the season for Denver. This great streak allowed him to cash in during free agency. He did so by signing with the Houston Texans to be their new starter.

The only issue with Osweiler is that he is not a good quarterback. Especially when moving from a talented team like Denver to an also-ran like Houston was at the time.

He spent one season as the starter in Houston, completing only 59% of his passes for 15 TDs and 16 INTs for less than 3,000 yards. It was so bad that after the season, Houston gave Osweiler and two draft picks, including a second-round selection, to Cleveland for a late-round pick just so Cleveland would eat the contract it did not want anymore.

.@HoustonTexans have traded QB Brock Osweiler to the Cleveland Browns. Terms of trade were not disclosed. Quote from #Texans GM Rick Smith: pic.twitter.com/M8boKSkdDW

— Houston Texans PR (@TexansPR) March 9, 2017

Byron Maxwell, Philadelphia Eagles (6 years, $63 million, 2015)

Maxwell came into the league in 2011 from Clemson and immediately entered one of the best secondaries of this generation.

Joining the Legion of Boom in Seattle, Maxwell was a solid role player behind Earl Thomas III and Richard Sherman. With this surrounding cast, it was easy for Maxwell to be hidden by better players.

The group led by Thomas and Sherman led the Seattle Seahawks to a Super Bowl win following the 2013 season, and when Maxwell went into free agency in 2015, Philadelphia figured it could get a piece of that secondary. Too bad for the Eagles; they got the lemon.

Hidden by the rest of his teammates in Seattle, Philadelphia failed to see Maxwell's lack of ability. It immediately named him the No. 1 cornerback. He was no match for other teams' WR1, and after just one season, Maxwell was traded to the Miami Dolphins. Worse yet, the Dolphins released him just a year and a half later.

There are certainly more players who could make this list. From Albert Haynesworth and Kristian Wilkerson to J.C. Jackson and Kenny Golladay. But we went with some off-the-radar selections whose contracts were just as egregious. There are sure to be even more contenders for this list after the 2026 signings finish.

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