Skip to content 
The ending of the Super Bowl signals a momentary pause in the NFL universe, but you need not worry as that pause is only a brief one. Teams are immediately planning their roster building for the next season, with some having tens of millions in cap space to play with in free agency and some having to be a little more creative.
In March, free agency officially begins and while some teams spend big and strike gold, others will swing for the fences and miss completely. On that note, here are my five biggest free agent flops of the last twenty years.
Albert Haynesworth
In 2008, Haynesworth was an absolute monster for the Tennessee Titans, securing All Pro and Pro Bowl status for the second straight season and establishing himself as the most dominant interior defensive lineman in the league.
He wasn’t a stranger to controversy though. In Titans training camp in 2003 he kicked teammate Justin Hartwig in the chest after a disagreement. Then in 2006 he stomped on Cowboys centre Andre Gurode’s head, narrowly missing his eye and resulting in Gurode needing 30 stitches. He was banned for 5 games which was at the time the longest suspension ever handed out for an on-field incident.
All of this was in addition to multiple off field incidents, with several lawsuits ranging from traffic violations, child support, assault and failure to make payments on a loan being brought against him. The warning signs were clear but it didn’t stop infamous Redskins owner Dan Snyder from handing Haynesworth a seven year, $100 million deal in the capital – guaranteeing him a whopping $41 million.
There were problems from the off when Haynesworth refused to participate in offseason workouts and then failing to pass a basic fitness test upon his arrival to camp. He brazenly criticised the scheme used by defensive coordinator Greg Blache and was eventually suspended by head coach Mike Shanahan for “poor conduct and a refusal to cooperate with team policy”. In 2011, after only 20 games and 6.5 sacks, the ‘Skins cut ties and traded Haynesworth to the Patriots for a measly fifth rounder.
Brock Osweiler
In 2015, as Peyton Manning struggled with injury and poor form, Brock Osweiler stepped in and started seven games for the eventual Super Bowl champion Denver Broncos.
Osweiler was steady in guiding the Broncos to the playoffs (where Manning returned), completing 61% of his passes with 10 TDs and 6 INTs. Osweiler got a ring but that wasn’t all, as in free agency the Houston Texans gifted him a quite astonishing four year, $72 million deal with a eye-watering $37 million in guaranteed cash. Osweiler was nothing short of a disaster in southeastern Texas, managing to complete only 59% of his passes, with 15 TDs and 16 INTs in his only season as a starter. Perhaps most damning is that Osweiler lost his job to Tom Savage and was eventually traded to the Browns, where he also lost out to DeShone Kizer.
Deion Sanders
“Prime Time” is arguably the greatest corner to ever play in the NFL, but in 2000 the prime time of his career had undoubtedly fizzled out after being released by the Cowboys in a salary shedding move.
However, Daniel Snyder was once again waiting in the wings ready to give a superstar name an inexplicably huge sack of cash. He handed over a seven year contract worth a potential $56 million, with an $8 million signing bonus. At 32 years old, the length of the contract Sanders received was even more mind boggling than the money.
On the field, Neon Deion looked much older than 32, looking largely disinterested in tackling and snagging only 4 interceptions. He earned $2.4 million for the season and promptly retired, meaning Snyder had paid $10.4 million for one very poor season of work. Despite Sanders’ age, the Redskins would have expected to get more than one year out of him. Despite this, a seven year deal will always look preposterous.
DeMarco Murray
The 2014 season was a monster year for Cowboys running back Murray, as he romped to 1,845 yards rushing, 13 TDs and a shiny Offensive Player of the Year award for his cabinet.
Murray parlayed this into a huge contract with the Philadelphia Eagles, joining up with Chip Kelly in the City of Brotherly Love. The 2015 season was beyond underwhelming for Murray as he managed a meagre 702 yards on the ground whilst struggling to fit in with Kelly’s scheme. Kelly was also the GM, meaning that along with a terrible offensive line, it will be forever perplexing that he thought a north/south runner like Murray would fit in his scheme. Murray voiced his displeasure to owner Jeffrey Lurie and was eventually traded to the Titans the following year. His signing and subsequent failure was a catalyst for the firing of Kelly too, so maybe Eagles fans will always be thankful in a roundabout way.
Javon Walker
Wide receiver Javon Walker broke out with the Packers in 2004, racking up an impressive 1,400 yards. He continued to be productive in Denver too as he again broke the 1,000 yard barrier in 2006, before a terrible ACL injury struck him down in 2007.
Off field problems also began to emerge and the Broncos admitted defeat, releasing Walker after failing to find a trade partner willing to make a deal. This didn’t discourage the Oakland Raiders from handing Walker a truly startling six year, $55 million contract with $16 million in guarantees.
In his first season in the Bay Area he played in only 8 games and managed a woeful 15 receptions for just 196 yards. His second season was even more nondescript, playing in three games and failing to register a single statistic. Walker was released in March 2010 having cashed in a total of $21 million from Al Davis and the Raiders. Other names could have taken this place in the list of terrible signings, but Walker gets the nod because of the sheer magnitude of illogicality displayed by the Raiders front office in giving him that deal.
There were plenty of names that could have made this list (shoutouts to Matt Flynn, David Boston and Jevon Kearse), but these deals will always stick in the mind when it comes to disastrous free agent signings. Hindsight is a wonderful thing but, as illustrated by this list, some deals were never a good idea in the first place. With salary cap constraints and the need to fill a 53 man roster, free agency is a difficult road to navigate for every team in the NFL. If you get it wrong, the consequences can be long reaching and very, very hard to fix.
