Executives in charge of running National Football League teams are tasked with getting the absolute best values out of every contract possible for every season in order to stay underneath the league’s hard salary cap. This financial limit is meant to spread parity and give just about every club an opportunity to compete for playoff spots even if those teams played poorly the prior campaign. “Worst to first” is a catchy cliche often tossed out in the sports world, but it shouldn’t be ignored, the NFL is a competition where the league wants teams that finish near the bottom of standings one season to climb into playoff races the subsequent year. It is the nature of the salary cap and the league that makes the success enjoyed by the New England Patriots throughout the 2000s so impressive. Dynasties aren’t meant to exist in the modern NFL.
Because every team can, per league rules, only dedicate so much cash to players each year, even one horrible contract can ultimately sink a club’s championship hopes between the start of the NFL calendar year in March and the end of the playoffs. Some of the regrettable contracts featured in this piece are attached to former stars who are either no longer in their primes or who have failed to prove they were worth the money paid to them in the first place. What has to be considered the worst contract of 2017, as of the middle of August, belongs to a quarterback who probably shouldn’t have been signed by his current employer considering who that franchise selected in the first round of this year’s draft.
15 Brock Osweiler
Nobody should blame the Cleveland Browns for taking on the absolute albatross that is the contract belonging to quarterback Brock Osweilier earlier this year. After all, it was the Houston Texans, not the Browns, who elected to pay Osweiler a small fortune ahead of the 2016 season. In fact, the Texans are still on the hook for $9 million of the deal in 2017 even though Osweiler will never throw a single pass for the club this fall.
Meanwhile, the Browns could, theoretically, move on from Osweilier next winter without having to worry about any financial burden minus what the team has to pay him this year. Don’t feel too bad, Houston fans. At least your favorite team isn’t responsible for the undisputed worst QB contract of 2017.
14 Jonathan Stewart
Carolina Panthers running back Jonathan Stewart’s contract carries a cap hit of over $6.1 million, which is quite a hefty sum considering he turned 30-years-old earlier this year and he consistently fails to rush for 1,000 yards during seasons. Sure, Stewart found the end zone a total of nine times in 2016, but those scores didn’t prevent the Panthers from being one of the most disappointing teams of the campaign.
Logic suggests the Panthers could save some money and find similar production elsewhere, especially now that the team has rookie Christian McCaffrey in the backfield. The dead cap value of Stewart’s deal drops down to $1.5 million for 2018, meaning this may be the last season you see him playing for the Panthers before both entities move on.
13 Kenny Britt
The Cleveland Browns handing wide receiver Kenny Britt $17 million in guaranteed money is, on its own, not a horrible decision, but this contact becomes laughable when you remember who the Browns could’ve kept instead had the club been smart earlier this year.
Had the Browns placed the franchise tag on Terrelle Pryor this past February at a time when Cleveland had more than enough available cap space to afford doing so, Pryor, who is, physically speaking, better than Britt in every way, would be working with rookie Cleveland quarterback DeShone Kizer in practices this August. Instead, the Browns failed to secure Pryor’s services, he signed a one-year deal with the Washington Redskins, and the Browns had to settle on paying Britt more money than he's worth.
12 Blake Bortles
This example of a supposed horrible contract a team is regretting is more about “drafter’s remorse” than “buyer’s remorse.” Jacksonville Jaguars quarterback Blake Bortles has failed to improve since the club acquired him early in the 2014 NFL Draft, and there are serious doubts he’ll ever prove to be anything more than a journeyman backup.
Things look so gloomy for Bortles’ Jacksonville future in August, in fact, that the team has given backup Chad Henne some practice reps with starters over Bortles. In total, the Jaguars have paid a little over $20 million in guaranteed money to Bortles over the years. Imagine where the club would be today had the Jaguars spent that money on Khalil Mack, Mike Evans or Odell Beckham, all of whom were drafted after Bortles in 2014.
11 Coby Fleener
One would think teams would know, by now, that paying a tight end a large sum of money is rarely worth it unless that man happens to be one of the top-three players at the position. The contract belonging to New Orleans Saints tight end Coby Fleener has a cap hit of $7.5 million and a dead cap value of $12.2 million for the 2017 season, and those two figures are astonishing considering he is averaging three touchdowns per season over his past two years.
He caught only 50 passes in 2016 as a member of the New Orleans offense despite playing in 16 games, and there is currently no indication the 28-year-old will become a revelation during his second campaign with the Saints. The book may be out on the former Indianapolis Colts player.
10 Tavon Austin
Odds are you probably won’t have to look far to find Los Angeles Rams wide receiver Tavon Austin listed among the worst NFL contracts and, dare we say, the worst draft picks in recent memory. In August 2016, the Rams signed Austin to a four-year extension that could be worth up to $42 million despite the fact the 26-year-old still hasn’t come remotely close to earning that type of pay with his play.
Anybody doubting that to be true need only realize the Rams traded for Sammy Watkins, who has struggled remaining healthy throughout his career, in August, and that transaction has led more than a few people to believe the team could look to trade Austin if the Rams can find a franchise willing to take his contract.
9 Russell Okung
It was not all that long ago when the Los Angeles Chargers paying offensive tackle Russell Okung at least $25 million in guaranteed money and possibly up to $53 million over four years wouldn’t have been such a crazy notion. Okung has clearly not been the player of old throughout the past several seasons, however, and the Denver Broncos declined his option for 2017 after the club deemed him to not be worth what would’ve been owed to him for the upcoming season.
While Okung’s cap hit is only at $6 million for the 2017 campaign, that value skyrockets up to $15 million next year. He’ll need to turn the figurative clock back and find Pro Bowl form to silence critics who believe his signing was a regrettable error.
8 Clay Matthews
A dilemma NFL teams often face is whether or not to pay top defensive players, and how much money to award to men who aren’t quarterbacks and top-tier offensive stars. Nobody thought much of it, at the time, when the Green Bay Packers gave linebacker Clay Matthews over $20 million in guaranteed money and a contract potentially worth up to $66 million across five years.
Matthews has failed to match the numbers he produced in 2012 when he accumulated 13 sacks by the end of the campaign, and he had only five sacks and 24 total tackles in 12 appearances in 2016. While Matthews remains one of the most recognized stars in the NFL thanks to a handful of marketing campaigns, the Packers may feel they need to move on next winter if the 31-year-old is nothing more than a serviceable player in 2017.
7 Sam Bradford
The Minnesota Vikings had to do something drastic after quarterback Teddy Bridgewater suffered a serious knee injury ahead of the 2016 season, which is why the club trading for Sam Bradford last September made sense. Think about this, though: The Vikings have $18 million in cap space associated with a QB who threw 20 touchdowns, an average of well under two per game, in his first season with the team. Is it really that hard to believe the Vikings couldn’t get similar production, if not better, for less money?
Controversy aside, Colin Kaepernick would be a cheaper option. Even Jay Cutler wouldn’t carry as high a cap hit for the 2017 season. Bradford can prove he’s worth his pay by guiding the Vikings to a playoff berth this year.
6 Alex Smith
A perception that has yet to be disproven is that quarterback Alex Smith is good enough to get you to the playoffs but cannot win the big game for the Kansas City Chiefs or with any other team. It’s clear the Chiefs are already thinking of a future without Smith, as the club selected Patrick Mahomes in the first round of the 2017 NFL Draft.
It’s believed Mahomes has impressed during training camp and the preseason process, and he could enter September as the backup on the roster. Smith’s contract carries a cap hit of $16.9 million for 2017, while Mahomes’ is on a deal worth a fraction of that price. The only way the Chiefs won’t be regretting the Smith contract is if he takes them to at least a conference title game.
5 Sean Lee
The reality here is that Dallas Cowboys linebacker Sean Lee is worth the $42 million contract the club gave him back in 2013 when he is fully healthy. Unfortunately, Lee has struggled with a variety of injury issues throughout his career, and he is already dealing with hamstring tightness this August.
Lee’s cap hit for 2017 is over $7 million, and that number rises to over $11 million before the start of next year. The Cowboys won the NFC East in 2016, and Dallas is, on paper, a contender to return to the playoffs and possibly expand on the success the team enjoyed last year. When you consider everything, it’s not a stretch to suggest the Cowboys wouldn’t be better off spending Lee’s money on other assets.
4 Joe Haden
At this point, it is barely a secret the Cleveland Browns are regretting giving cornerback Joe Haden a five-year contract worth $67.5 million in 2014. Haden, almost remarkably, has not been the same player throughout the past three seasons, and he’s also been slowed by injuries.
A variety of rumors existed in the fall of 2016 that the Browns were looking to trade Haden during the team’s latest attempted rebuild, but no club pulled the trigger on such a transaction. The Browns are now stuck with Haden eating up over $14 million in cap space for the upcoming season. Haden’s dead cap value drops to $3.2 million for 2018, meaning the Browns will likely either look to restructure his deal or move on from him next winter.
3 Richard Sherman
When he's at his best in the secondary, Seattle Seahawks cornerback Richard Sherman is worth his $13.631 million cap hit for the 2017 season. Remember, though, that we’re discussing contracts teams are regretting, and a clear sign a franchise is having second thoughts about a deal is when that club reportedly attempts to trade a player. This past offseason, there was far too much smoke regarding Sherman trade rumors to not believe there was nothing to those whispers, and the Seahawks even being slightly interested in trading the one-time Super Bowl champion says plenty about how Seattle has valued him over the past eight months.
The relationship between Sherman and the Seahawks could be one of the more fascinating stories to follow throughout the upcoming season.
2 Muhammad Wilkerson
Fans of the New York Jets can cross their fingers and hope, all they want, defensive end Muhammad Wilkerson bounces back and has a tremendous season. The Jets, nevertheless, are on pace to suffer through a disastrous campaign, and it’s only a matter of time before Gang Green either trades or cuts Wilkerson.
While Wilkerson’s cap hit goes up from $18 million for 2017 to $20 million next season, the dead cap value of that contract drops down to $9 million in 2018. There’s little doubt the Jets are more than a year away from being able to compete with the best teams in the AFC, which is why the club will be happy to jettison from Wilkerson’s contract if the opportunity to do so presents itself ahead of this year’s trade deadline.
1 Mike Glennon
The Chicago Bears gave quarterback Mike Glennon a three-year contract worth $45 million, $18.5 million in guaranteed money and, we all thought at the time, the starting job this past March. Then, the club moved up in the first round of the draft to grab QB Mitchell Trubisky in a move that shocked many football observers. Naturally, Trubisky has shined in practices and during the preseason, and it’s widely believed the rookie will start ahead of Glennon in 2017, perhaps as soon as September.
While the Bears can move on from Glennon after one season, that doesn’t change the fact that the team’s handling of the QB position during the first half of the year remains downright bizarre. Glennon’s contract has to be seen as the worst and most regrettable of the year.