17 NFL Legends Who Became Total Headaches Late in Their Careers

They were once the faces of franchises, the heroes of Sundays, and the pride of fanbases across the league. But as time wore on, these NFL legends traded highlight reels for headlines—and not always the good kind.

From contract disputes and bizarre behavior to locker room feuds and awkward exits, these players didn’t exactly ride off into the sunset. Whether it was ego, injuries, or just not knowing when to call it quits, here are 17 NFL icons who became total headaches late in their careers.

17. Warren Sapp

Jun 15, 2022; Ashburn, Virginia, USA; Washington Commanders defensive end Montez Sweat (90) jokes with special consultant and NFL Hall of Fame member Warren Sapp (R) on day two of minicamp at The Park. Mandatory Credit: Geoff Burke-Imagn Images
Geoff Burke-Imagn Images

Sapp was a force in the trenches and a surefire Hall of Famer, but his blunt attitude wore thin by the end. His time in Oakland was full of fines, sideline outbursts, and media squabbles.

16. Michael Strahan

Feb 3, 2008; Glendale, AZ, USA; New York Giants defensive end Michael Strahan (92) celebrates a sack on New England Patriots quarterback Tom Brady (12) during Super Bowl XLII at the University of Phoenix Stadium. Mandatory Credit: Mark J. Rebilas-Imagn Images
Mark J. Rebilas-Imagn Images

Strahan is now Mr. Morning Show, but his last few years in the NFL included messy contract disputes and threats to retire every offseason. The Giants loved his talent, but not always the drama.

15. Brett Favre

Green Bay Packers quarterback Brett Favre is able to get off a pass despite being dragged by Detroit Lions Luther Ellis during the second quarter of their game on Dec. 10, 2000 at Lambeau Field in Green Bay, Wis
Dale Guldan / Milwaukee Journal Sentinel / USA TODAY NETWORK via Imagn Images

Favre’s on-field greatness was matched only by his inability to retire with dignity. The constant will-he-or-won’t-he routine became an annual headache for multiple teams.

14. Richard Sherman

San Francisco 49ers cornerback Richard Sherman (25) reacts during Super Bowl LIV against the Kansas City Chiefs at Hard Rock Stadium.
Mark J. Rebilas / Imagn Images

Once the mouthpiece of the Legion of Boom, Sherman’s late-career tenure included injuries, public call-outs, and off-field headlines that overshadowed his declining play. He went from elite corner to lightning rod fast.

13. Tiki Barber

Jan 7, 2007; Philadelphia, PA, USA; New York Giants running back (21) Tiki Barber carries the ball against the Philadelphia Eagles in the first quarter of the NFC Wild Card Playoff game at Lincoln Financial Field in Philadelphia, PA. The Philadelphia Eagles defeated the New York Giants 23-20 in what was reported to be Tiki Barber's last NFL game. Mandatory Credit: James Lang-Imagn Images Copyright © James Lang
James Lang-Imagn Images

Tiki walked away from the game at his peak, only to spend his retirement pot-stirring from the sidelines. His criticism of former teammates and a failed comeback attempt didn’t exactly endear him to fans.

12. Randy Moss

San Francisco 49ers wide receiver (84) Randy Moss runs for a third quarter touchdown against the Arizona Cardinals at University of Phoenix Stadium.
Mark J. Rebila / Imagn Images

Moss was unstoppable in his prime, but his attitude shift in later years made things rocky. Whether it was dogging routes or being openly unhappy in interviews, he brought plenty of drama.

11. Antonio Brown

Jan 3, 2021; Tampa, Florida, USA; Tampa Bay Buccaneers wide receiver Antonio Brown (81) smiles after scoring a touchdown against the Atlanta Falcons during the second half at Raymond James Stadium. Mandatory Credit: Kim Klement-Imagn Images
Kim Klement-Imagn Images

Brown went from All-Pro to all-problem in a matter of seasons. His late-career antics—ranging from frostbitten feet to helmet grievances—turned every locker room into a circus.

10. Jay Cutler

Jay Cutler throws a deep pass against the Buffalo Bills
Mark Konezny / Imagn Images

Cutler always had a polarizing personality, but his final NFL seasons were defined by apathy and a general “meh” vibe. His body language alone made fans and coaches lose their minds.

9. Donovan McNabb

Donovan McNabb celebrates his fourth-quarter touchdown pass to Chad Lewis
William Bretzger / Imagn Images

McNabb’s fall from grace included ugly stints in Washington and Minnesota, plus some strange media takes post-retirement. It was a tough watch for a guy who once ran the NFC.

8. Le’Veon Bell

Oct 1, 2017; Baltimore, MD, USA; Pittsburgh Steelers running back LeVeon Bell (26) runs for a gain against the Baltimore Ravens at M&T Bank Stadium. Mandatory Credit: Mitch Stringer-USA TODAY Sports
Mitch Stringer-Imagn Images

Bell’s standoff with the Steelers set the stage for a strange second act. He never regained his elite form and bounced between teams while calling out coaches and hinting at a boxing career.

7. Dez Bryant

Dec 27, 2020; Baltimore, Maryland, USA; Baltimore Ravens wide receiver Dez Bryant (88) strikes his familiar X pose prior to the game against the New York Giants at M&T Bank Stadium. Mandatory Credit: Mitch Stringer-Imagn Images
Mitch Stringer-Imagn Images

Dez was a touchdown machine in his prime, but his sideline blowups and off-field noise became a major distraction. Late in his career, he struggled to land gigs while continuing to talk big.

6. Terrell Owens

Cincinnati Bengals wide receiver Terrell Owens (81) looks to the bench after missing a pass during the second half against the New England Patriots at Gillette Stadium. The Patriots defeated the Bengals 38-24.
David Butler II / Imagn Images

Owens is one of the most talented wideouts ever, but his final years were a carousel of team drama, reality TV, and Twitter rants. He never quite stopped campaigning for one more shot.

5. Cam Newton

Carolina Panthers quarterback Cam Newton
Crystal LoGiudice / Imagn Images

Newton brought swagger and an MVP trophy to Carolina, but his post-prime seasons were defined by cryptic social media posts, odd fashion statements, and subpar play. He stayed in the spotlight, just not always for the right reasons.

4. Albert Haynesworth

Tennessee Titans defensive tackle Albert Haynesworth (92) pressures New York Jets quarterback Chad Pennington (10) at LP Field in Nashville on Sep. 10, 2006. The Titans lost their home and season opener 23-16
George Walker IV / Imagn Images

After cashing in with a monster contract, Haynesworth’s effort level plummeted. He clashed with coaches, ignored conditioning, and quickly became one of the league’s most expensive problems.

3. Odell Beckham Jr.

Cleveland Browns wide receiver Odell Beckham Jr. (13) runs a route during training camp at the Cleveland Browns training facility.
Ken Blaze / Imagn Images

OBJ’s late-career image has been more about fashion shows, sideline tantrums, and cryptic tweets than consistent play. The hype stayed, but the production didn’t always follow.

Read More: 15 Most Respectful Rivals in Sports History

2. Ben Roethlisberger

Pittsburgh Steelers quarterback (7) Ben Roethlisberger and wide receiver (86) Hines Ward wait during a time out against the Cincinnati Bengals at Paul Brown Stadium. The Steelers won 24-13.
Frank Victores / Imagn Images

Big Ben brought Pittsburgh two rings, but the final chapters of his career included passive-aggressive media comments, locker room leaks, and a refusal to admit when it was time to hang it up. The decline was tough to ignore.

Read More: Ranking the 30 Best Quarterbacks of All Time

1. Aaron Rodgers

Jun 10, 2025; Pittsburgh, PA, USA; Pittsburgh Steelers quarterback Aaron Rodgers during minicamp at their South Side facility. Mandatory Credit: Philip G. Pavely-Imagn Images
Philip G. Pavely-Imagn Images

Rodgers’ twilight years have included everything from vaccine controversy to offseason retreats and cryptic interviews. He’s still got talent, but the drama has started to outweigh the dimes.

Read More: From Burrow to Young: Ranking The Top 10 Most Epic QB Performances in College Football Ever

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