The 5 worst offseason moves in NFL history

NFL owners aren’t shy about taking out their wallets and plunking down enormous sums of cash in front of free agents. Yet, maybe they should.

In some instances, even the biggest and most notable star players have struggled in new locations on their NFL new teams. As we peek around today’s landscape, it’s difficult to pinpoint who will become the next player to struggle after being given an enormous contract.

Will Von Miller live up to the hype in Buffalo after being handed a six-year deal worth $120 million? How about Davante Adams? Now that he has his money, will he live up to the five-year, $141 million contract given to him by the Las Vegas Raiders?

All of those questions will be answered this season. But before we find out which moves were sagacious, let’s look back at some of the most horrendous offseason moves in NFL history.

#1. Daunte Culpepper

Minnesota Vikings v Detroit Lions

At one point, Daunte Culpepper was a terrific NFL quarterback. In 2003 and 2004, in particular, the light switch went off. The former Minnesota Viking made back-to-back Pro Bowls and led the Vikings to respectability. In 2004, he led the entire NFL in passing yards, throwing for 4,717 to go along with 39 touchdowns.

Unfortunately for Culpepper, his career took a turn for the worse during the 2005 season. Halfway through the year, Culpepper crumbled to the turf with a torn ACL, MCL, and PCL in his knee. For whatever reason, the Miami Dolphins believed they could get Culpepper’s career back on track. In exchange, the franchise handed over a 2006 second-round pick to the Vikings but quickly moved off him.

In only four games, Culpepper was a shell of his former self, leading the Dolphins to only one victory during his time as a starter while throwing two touchdowns and three interceptions.

#2. Nick Foles

Chicago Bears v Jacksonville Jaguars

Nick Foles effectively turned two of the best years of his career into life-changing money with the Jacksonville Jaguars. In 2017, the hopes and dreams of the Philadelphia Eagles were pinned firmly on the shoulders of Foles.

With Carson Wentz forced to miss the entire NFL postseason due to a torn ACL, Foles was asked to step up. To the surprise of many, he would do so in a big way.

Foles and his Eagles took care of business throughout the playoffs, resulting in an unlikely Super Bowl ring. The following year, Wentz went down with another injury before the playoffs, with Foles again leading them on another deep run.

The Jaguars saw more than enough out of Blake Bortles and opted to go in another direction, handing Foles a four-year deal worth $88 million. In the first game of the NFL 2019 season, Foles suffered a broken Clavicle. While he would eventually return several months later, he did deliver his best.

In just one season, the Jaguars decided against keeping Foles as their long-term solution as their starter, going with Gardner Minshew and sending Foles to the Chicago Bears.

#3. Matt Flynn

Green Bay Packers v Miami Dolphins

Throughout our infamous list and littered across NFL history, players have inked enormous contracts due to a stellar breakout season. Maybe even two. Never, however, has a player been rewarded due to one game. Well, meet Matt Flynn.

With a historically significant season already wrapped up, Aaron Rodgers and the Green Bay Packers were on their way to the NFL postseason in 2011 after putting together a 14-1 record. In the season's final game, Rodgers sat on the sidelines, as did many of the starters. In his place, of course, was backup Matt Flynn.

A relative unknown at this point, Flynn turned several heads with his jaw-dropping performance. Flynn threw for 480 yards, completing 31 of his 44 passes and lofting six—yes, six!—touchdowns into the end zone. The Seattle Seahawks believed the then 27-year-old was their quarterback of the future, inking him to a three-year deal worth $19 million.

Shortly after, Flynn was outplayed in training camp by rookie Russell Wilson. Flynn became expendable and was traded the following year to the Buffalo Bills.

#4. Brock Osweiler

Divisional Round - Houston Texans v New England Patriots

Quarterbacks don't usually come in Brock Osweiler's size. The former second-round pick stood at 6'7" and weighed 240 pounds. But despite his enormous dimensions, Osweiler was far from impressive.

Yet, regardless of his unimpressive play, the Houston Texans gave the middling quarterback a four-year deal worth $72 million. Overall, Osweiler was solid, throwing 2,957 yards and 15 touchdowns, but his 16 interceptions and 59 percent completion rate were awful.

The Texans accepted that they had made a huge mistake and got rid of the gargantuan quarterback. Osweiler only proved that the Texans were right to cut ties. At the age of 28, after bouncing around a bit more, Osweiler was ushered out of the league. However, before finding himself without a job, Osweiler attempted to revitalize his career by returning to Denver. Needless to say, it was a disaster.

Osweiler started four games back in his old stomping grounds but exhibited many of the same problems that have always plagued him. He would lose every game as the team's starter and completed only 55.8 percent of his passes. He was also not the best in the pocket, throwing five touchdowns and five interceptions.

#5. Albert Haynesworth

Denver Broncos v Washington Redskins

As a Tennessee Titan, Albert Haynesworth was arguably the best defensive tackle in the NFL. In 2007 and 2008, Haynesworth truly stood out. He finished the year with 14.5 combined sacks and 91 combined tackles. His numbers resulted in back-to-back Pro-Bowl appearances and consecutive All-Pro berths.

Haynesworth's best seasons were rewarded with a ridiculous deal worth $100 million for seven years with the Washington Redskins. Ultimately, the financial ramifications were a tough pill to swallow. Still, Washington believed Haynesworth was a franchise-altering kind of player and one they needed to get themselves over the championship hump.

Once Haynesworth got his money, his motivation went entirely out the window. He reached well over 300 pounds, appeared lethargic, and had uninspiring performances on the pitch.

In year one, Haynesworth recorded just four sacks in 12 games. During the following season, they were done with him. He didn't start a single game before being shown the door the following year.