Every NFL offseason is full of bold declarations, splashy signings, and trade blockbusters that get fans dreaming big. But not every move ends up looking like a genius stroke—some start to stink faster than a forgotten gallon of 2% in the back of the fridge.
Whether it was a free agency overpay, a head-scratching trade, or a coaching hire that never clicked, these moves had people excited… until the games actually started. From quarterback flops to instant-regret contracts, here are 16 offseason decisions that aged terribly in the bright light of hindsight.
16. The Browns Trade for Brock Osweiler
The Browns basically bought a second-round pick by taking on Osweiler’s bloated contract, but pretending he was their starter was a reach. He never played a regular-season snap for Cleveland—thankfully.
15. The Jets Sign Le’Veon Bell
The Jets broke the bank for Bell after he sat out a full year, hoping he’d be their offensive savior. Instead, he looked like he still had his feet up on the couch.
14. The Broncos Trade for Joe Flacco
Denver brought in Flacco as a “win-now” veteran presence. The only thing he won was the race to the bench.
13. The Raiders Sign Antonio Brown
Antonio Brown to the Raiders was supposed to be electric. It turned into a chaotic circus that ended before he even played a game.
12. The Jaguars Pay Big for Nick Foles
Fresh off a Super Bowl MVP, Foles got paid big money to lead Jacksonville. He broke his collarbone in Week 1 and was never the guy again.
11. The Bears Trade Up for Mitch Trubisky
Trading up to grab Trubisky over Mahomes and Watson? That move will haunt Bears fans for generations.
10. The Patriots Sign Jonnu Smith and Hunter Henry
Double tight ends, double trouble. The Patriots went all-in, but the production never came close to matching the price tags.
9. Washington Signs Albert Haynesworth
One of the biggest free agency flops ever. Haynesworth cashed in, then checked out.
8. The Colts Trade for Carson Wentz
The Colts thought Wentz just needed a change of scenery. Turns out, what he needed was a reset button.
7. The Texans Trade DeAndre Hopkins
Bill O’Brien gave away one of the league’s best receivers for peanuts. The Texans’ offense hasn’t been the same since—and neither has the front office.
6. The Dolphins Sign Mike Wallace
Wallace was paid like a WR1 and delivered like a WR3. Miami quickly learned that speed isn’t everything.
5. The Seahawks Trade for Percy Harvin
Seattle gave up a lot to get Harvin, who was more injury-prone and drama-filled than productive. His Super Bowl return TD was a moment, but the rest? Forgettable.
4. The Saints Sign Jairus Byrd
Byrd was supposed to be a game-changing safety. Instead, he became a cautionary tale in free agency spending.
Read More: 20 Times a Superstar NFL Signing Backfired
3. The Cardinals Sign Emmitt Smith
An aging Emmitt in Arizona just didn’t make sense. He looked out of place from the moment he put on that uniform.
Read More: 20 NFL Stars Who Lived Like It Was Always the Offseason
2. The Jets Sign Neil O’Donnell
Fresh off a Super Bowl appearance with Pittsburgh, O’Donnell was supposed to be the Jets’ savior. Instead, he flamed out fast and left the fanbase bitter.
Read More: The 20 Worst Free Agent Signings in NFL History
1. The Vikings Trade for Herschel Walker
The Vikings made the move—and it might be the worst in NFL history. Dallas got a haul, and Minnesota got buyer’s remorse on a gold-plated platter.
