Releasing players who are still owed lots of guaranteed money is hot these days. Nothing says ‘this was a terrible contract’ more than letting a guy walk and still paying him oodles and oodles of money to not play football for your team.
So let’s go back in recent history and take a look at some of the worst NFL Free Agency contracts over the last decade. Obviously, these are mostly quarterbacks; they get paid the most. But we’re also going to sprinkle in a couple of other guys too. Let’s get three of the hard hitters out of the way first.
Deshaun Watson, 2021
There’s only one spot to start when it comes to the worst contracts in the past 10 years, and that's the one the Browns gave Deshaun Watson in 2021.
In 2020, he threw 33 touchdowns and seven interceptions, and led the NFL with 4,823 passing yards. It was a really good season for him… and then he was accused of sexual assault by almost two dozen massage therapists.
He sat out for the entire 2021 season, and then, despite knowing everything going on with Watson, the Browns traded three first-round picks for him… AND THEN gave him a fully guaranteed (which doesn’t happen) five-year contract for $230 million.
In the four years since, Watson has played in 19 of a possible 51 games, and has looked terrible for about 99% of the snaps he took. Oh, and he tore his Achilles in October of 2024, and then re-tore it in January of 2025.
Russell Wilson, 2022
That whole Russell Wilson trade saga in 2022 was weird. There were three or four teams that wanted him, and they all lucked out. Hell, there’s an alternate universe where the 2022 Eagles QB1 and WR are DangeRuss and Allen Robinson… That would’ve been gross.
Anyway, the Broncos ended up trading two firsts, two seconds, and a fifth-round pick (and three players) to Seattle for him. Then, when he got to Denver, he signed a five-year extension for $245 million, $165 million of which was guaranteed money.
Yada yada yada, he stinks. Yada yada yada, he jogs up and down a plane during an overseas flight. Yada yada yada, he has his own office and everyone hates him. Yada yada yada, “Broncos Country, let’s ride.”
The Broncos released him on March 4th, 2024, and took an NFL record $98 million dead cap hit. They ended up recovering from it: they just won the AFC West for the first time in 10 years, and made it to the AFC Championship game… But that doesn’t stop it from being a really bad contract.
Tua Tagovailoa, 2024
I think we all saw the Tua Tagovailoa thing playing out this way, right? When he signed his four-year extension for $212-ish million ($167 million guaranteed), no one thought, ‘Hell yeah, the Dolphins got their guy.’ It was much more of a, ‘Uhh, you sure about that?’
At that point, he’d already been missing all kinds of games because of his concussion trouble, but in 2023 he led the NFL with 4,624 passing yards… So, you could see why they wanted to get him locked up, but it didn’t really outweigh his lack of overall success.
Fast forward two years: Mike McDaniel gets fired, Tua gets benched, and the Dolphins do the Broncos a solid by cutting him and setting a new record with a $99 million dead cap hit. That’s a tough stretch right there.
Le’Veon Bell, 2019
Unless you’re a Jets fan, it’s fun to revisit the Le’Veon Bell catastrophe once every couple of years.
He was so sick in 2017 with the Steelers. He led the league in carries (321), had the second-most scrimmage yards (1,946), and the third-most rushing touchdowns (9). He was all about burst, physicality, vision, patience, and playmaking.
2018 came, and the Steelers said that they were going to franchise tag him for the second year in a row. Bell said if they did that, he wasn’t going to sign it because he wanted to get paid for the value that he brought to the team (whatever that means), and he’d sit out for the season.
So, the Steelers franchised-tagged him, Bell didn’t sign the tag, and sat out for the entirety of the 2018 season.
2019 free agency comes along, and Bell is a free agent. He ended up signing a deal with the Jets (after he released another album). It was for years for $52.5 million ($13.1 million per year, $35 million guaranteed). This made him the second-highest paid running back in the NFL at the time (behind Todd Gurley).
In that 2019 season, his efficiency dropped big time. He had 245 carries for 789 yards and three touchdowns. That was the 11th-most amount of work and the 24th-best production.
2020 came, and Bell hurt his hamstring, got put on IR, and liked tweets that said the Jets should trade him. The Jets couldn’t find a trade partner, so they released him and took a hit of $19-ish million in dead money.
Oh, and then the Chiefs picked him up, and they didn’t win the Super Bowl that year. So, tough for everyone involved.
Mike Glennon, 2017
The three best ways to make money in this world are by getting in a non-fatal plane accident so you can sue the airlines for a million-billion dollars, suing the city because you were accidentally sewn in the pants of the Charlie Brown balloon at the Thanksgiving parade, or by having a couple of fine seasons as a backup quarterback in the NFL. Mike Glennon chose the latter.
In 2013, Glennon was drafted by the Buccaneers in the third round. He started 13 games after Greg Shiano benched Josh Freeman. He threw for 2,608 yards and 19 touchdowns. In 2014, Josh McCown was Tampa’s quarterback, but Glennon got to start five games when McCown hurt his hand. In those games, he threw for 1,417 yards and six touchdowns.
In 2015, the Buccs picked Jameis Winston first-overall in the draft, and Glennon didn’t see the field. In 2016, he only threw 11 total passes. So obviously, there was only one thing that could happen: the Bears signed him to a three-year deal for $45 million ($18-ish million guaranteed) in 2017.
He started four games before the Bears moved on to Mitch Trubisky.
Brock Osweiler, 2016
Remember in 2015, how Peyton Manning was so broken down that he missed seven games so he could get healthy and go win a Super Bowl? The quarterback who came in to replace him was Brock Osweiler.
To be fair to him, he played perfectly fine. He got the ball to Demaryius Thomas and Emmanuel Sanders, and he did his best to limit turnovers. He wasn’t good or anything like that, but he (and mostly the defense) won five games and didn’t fall out of first place in the AFC. That’s a perfectly fine performance by a backup.
Bill O’Brien and the Houston Texans saw that, and couldn’t let him get away. In 2016, they signed him to a four-year deal for $72 million ($18 million per year, and a whopping $37 million guaranteed).
Osweiler would then throw 15 touchdowns and 16 interceptions in 2016 before he got benched for Tom Savage. Savage got a concussion in the last game of the season, so Osweiler started in the wild-card round of the playoffs… a game that the Texans won. But in the divisional round, he threw a pair of fourth-quarter interceptions, and they lost 16-34.
They traded him to the Browns a couple of months later.
Bryce Huff, 2024
Is this one all that bad? In the grand scheme of things, no… But Go Birds, so I think it is.
When Haason Reddick left the Eagles after the 2023 season, Howie Roseman knew that his defense was going to be missing a whole lot of production at the edge rusher position.
He made a little bit of a gamble by signing Bryce Huff, the Jets’ 2020 UDFA, who was coming off a 10-sack season. Did he think that he knew something the rest of us didn’t know, or was he feeling himself a little bit after signing Saquon Barkley? We’ll never know.
All we know is that Huff inked a three-year deal for $51.1 million ($17 million per year, $34 million guaranteed). After that? Don’t worry about it.
He never really clicked in the Vic Fangio defense. He was getting knocked off his feet by tight ends in the run game, and he was wholly inefficient as a pass rusher.
He ended up missing a handful of games because of wrist surgery, and then he was a healthy scratch in the Super Bowl.
The Eagles traded him to the 49ers before the 2025 season. In that trade, both teams decided to share the load of the bad contract: the Eagles paid nine-ish million of the remaining guaranteed money, and the 49ers paid six-ish.
Then, on March 12, 2026, Huff announced that he was retiring from the NFL at 27 years old. Get in, make $34 million, and get out. Not a bad gig on his side.