A.J. Brown and the NFL's 10 Messiest Player-Team Breakups Since 2000

The fallout of the Philadelphia Eagles and A.J. Brown split continues to settle. While Brown had a very successful four-year stint with the Eagles—one that included a Super Bowl ring—it also ended with a strained relationship that was evident during a disappointing 2025 campaign.

"Not every moment I can say I handled the best way," Brown told Maria Taylor on 7PM in Brooklyn following his trade to the New England Patriots (h/t Bleacher Report's Julia Stumbaugh).

Brown's situation in Philadelphia this past season was messy enough that his June 1 trade was expected—and the media has closely watched his final interactions with the franchise. In the grand scheme of things, however, it may have been more awkward than ugly.

Where does Brown's breakup with the Eagles rank among this century's messiest splits? Let's take a look.

Honorable Mention: The 49ers and Brandon Aiyuk

AP Photo/Ben VanHouten, File

This one clocks in as an honorable mention, only because the split between Brandon Aiyuk and the San Francisco 49ers hasn't officially been completed. However, it's shaping up to be one of the messiest NFL divorces of the modern era.

Things began brewing last season while Aiyuk was recovering from the prior season's devastating knee injury. The Athletic's Dianna Russini and Michael Silver reported in November that the 49ers weren't happy with Aiyuk's approach to his recovery and had voided his 2026 guarantees as a result.

Most expected Aiyuk to be released this offseason and for San Francisco to wash its hands of the situation. Instead, the 49ers have held onto Aiyuk's contract, hoping they can eventually get something in return via a trade.

To say that Aiyuk hasn't been pleased with the 49ers' approach would be an understatement.

"They mad 'cause they stupid. They dumb," Aiyuk said in an Instagram video (h/t NFL.com's Grant Gordon). "They mad that they paid me $50 million in eight months and then voided my guarantees for 2027. And I'm about to be on a new team in 2027."

Most likely, Aiyuk will eventually be with another team. However, he's ensured that his remaining time in San Francisco is extremely messy.

10. The Eagles and A.J. Brown

AP Photo/Terrance Williams

To be clear, Brown's split with the Eagles hasn't been clean. The receiver publicly voiced his frustrations with the Eagles and their offense during the 2025 season, and Philly did nothing to mask its intentions to move on from him in 2026.

While the Eagles didn't try to aggressively move Brown, at least not publicly, they did foreshadow his departure. They signed Marquise Brown, traded for Dontayvion Wicks, and used a first-round pick on Makai Lemon.

According to Jeremy Fowler, Sarah Barshop, Mike Reiss, Daniel Oyefusi, and Tim McManus of ESPN, Brown wanted out because of his waning chemistry with quarterback Jalen Hurts:

"A good bit of his angst stemmed from the play of Hurts, league sources said, in part because of Hurts' perceived reluctance to target Brown on tight-window throws against zone coverage."

Still, the two sides didn't publicly attack one another, as other teams and players on this list have done. Philly ultimately got a strong return from New England, and Brown landed in a favorable situation.

The relationship became strained, and the split long felt inevitable. However, this breakup felt more like a case of things running their course and less like a bitter separation.

9. The Broncos and Jay Cutler

AP Photo/Michael Dwyer

Back in 2009, the Denver Broncos traded quarterback Jay Cutler following a series of events that Broncos' Hall of Famer John Elway called "sad and unfortunate."

The friction started when the Broncos fired longtime head coach Mike Shanahan and replaced him with Josh McDaniels. Denver's new head coach then began shopping Cutler without the quarterback's knowledge. This didn't sit well with Cutler, who eventually requested a trade publicly.

Cutler's agent, Bus Cook, told ESPN's Chris Mortensen then that while Cutler was ready to commit to Denver, the Broncos weren't willing to commit to him.

The drama surrounding the stretched relationship overshadowed the early 2009 offseason before Cutler was traded to the Chicago Bears. The rapidly increasing discontent made the split feel especially messy at the time, though Cutler was happy to be in Chicago by the summer.

"I think both sides would change certain things and go about it a different way, but I think both sides are happy now and we're moving on," Cutler told reporters.

8. The Seahawks and Earl Thomas

AP Photo/Elaine Thompson, File

While Cutler's situation with the Broncos snowballed rather quickly, Earl Thomas' 2019 split with the Seattle Seahawks was more than a year in the making. It began when one of Seattle's last remaining defensive stars tried holding out for a new contract.

The previous offseason, Thomas skipped all of training camp and the preseason, hoping to pressure Seattle into a new deal. He never got it, but he did report in time to play in Week 1 of the 2018 season.

Then, in Week 4, Thomas' storied tenure with Seattle came to an abrupt halt. He was carted off the field with a season-ending leg fracture, and as he was heading to the locker room, he made his feelings about the situation very clear.

Thomas literally gave his own team the middle finger as he exited his final game as a Seahawk. The standout safety clearly blamed the Seahawks for putting him in a no-win situation.

"That's the crazy part of our business," linebacker Bobby Wagner said, per Oliver Connolly of The Guardian. "If he doesn't come, then he's not a team player. If he does come and gets hurt, it's he shouldn't have come."

Rarely do franchise legends experience the sort of exit that Thomas had from Seattle.

7. The Jets and Aaron Rodgers

AP Photo/Seth Wenig

There were no literal middle fingers given during Aaron Rodgers' 2025 split with the New York Jets—that we're aware of—but the Jets gave Rodgers a bit of a metaphorical finger on his way out of the door.

The split followed a tumultuous two-year run in New York that included Rodgers missing almost all of Year 1 with a torn Achilles and the firing of both coach Robert Saleh and GM Joe Douglas in Year 2.

Rodgers told The Athletic's Zack Rosenblatt that he flew to New York early in 2025 to speak with new head coach Aaron Glenn, only to be told he wouldn't be back.

"I felt there wasn't an ample amount of respect in that meeting. I guess I shouldn't have been surprised based on some things I saw over two years," Rodgers said, per Rosenblatt.

Rodgers' 2023 exit from the Green Bay Packers was weird—darkness retreat and all—but it did culminate with a trade to New York, which Rodgers wanted. His exit from the Jets was downright messy.

6. The Packers and Brett Favre

AP Photo/Rick Havner, File

Green Bay's transition from Rodgers to Jordan Love in 2023 was uncomfortable. Its transition to Rodgers from Brett Favre in 2008 was downright messy.

Early that offseason, things seemed to be going smoothly. Favre announced his retirement in March, leaving the Packers free to pivot to their 2005 first-round pick, Rodgers.

By July, though, Favre was interested in a return. He requested his release from Green Bay, which was denied, and he then filed for reinstatement. The Packers then filed a tampering charge against the rival Minnesota Vikings for alleged contact with Favre.

Favre was eventually shipped off to the Jets in a trade. He spent one season in New York before talking retirement again, getting his release from the Jets, and eventually signing with those pesky Vikings.

The separation was ugly at the time and led to Favre and the Packers being rivals for two seasons. However, the two sides have since mended fences. Green Bay retired Favre's No. 4 jersey in 2015, and the quarterback took the blame for starting the whole mess.

"It's over and done with. I was at fault," Favre told WGR 550-AM in 2013 (h/t ESPN).

5. The 49ers and Terrell Owens

AP Photo/Denis Poroy

Terrell Owens' 2004 split with the San Francisco 49ers was messy on multiple fronts.

It was messy because of how it transpired. Owens believed that he would be a free agent in 2004, but San Francisco asserted that his agent, David Joseph, failed to file the necessary paperwork in time to void the remainder of his contract.

"Terrell Owens did not exercise his option in a timely fashion, which is what is required," NFL spokesman Michael Signora said in February 2004, per Kevin Lynch of the San Francisco Chronicle.

This led to an unusual situation in which Owens believed he was free to negotiate with other teams, while the 49ers worked on a trade to send him to the Baltimore Ravens.

NFLPA eventually filed a grievance on Owens' behalf, and the NFL worked out an agreement with the 49ers, Ravens, and Philadelphia Eagles to resolve the situation. San Francisco and Baltimore both received compensation, while Owens landed with the team he had planned to sign with as a free agent.

While things didn't get as ugly as they could have in this situation, it's clear that Owens remained unhappy for some time. When asked by TMZ in 2018 which team he'd represent when inducted into the Hall of Fame, the receiver responded "It won't be the Niners."

4. The Buccaneers and Antonio Brown

AP Photo/Adam Hunger, Archive

Antonio Brown's 2019 split with the then-Oakland Raiders was messy in a conventional sense. He was sent to Oakland after requesting a trade from the Pittsburgh Steelers. Then, following a bizarre series of events, he was released before ever playing a game with the franchise.

Brown's release came after he suffered a cryotherapy injury while away from the team, briefly refused to wear an NFL-certified helmet, missed multiple meetings and practices, and engaged with GM Mike Mayock in an argument.

However, his break with the Tampa Bay Buccaneers in January 2022 was equally messy and exponentially more shocking.

After winning the Super Bowl with Tampa in 2020, Brown returned on a one-year deal. His up-and-down second season with the Bucs ended in Week 17 against the Jets, when the receiver removed his helmet, shirt, and pads, waved to fans in the end zone, and walked off the field and out of the stadium.

After the fact, Brown explained that his actions were a reaction to Tampa asking him to play hurt and not involving him in the offense.

"You don't want to throw me the ball and you making me like I'm crazy, so, I was like, 'I'm crazy, f--- all you motherf---ers, I'm out of here.'" Brown said on Tyreek Hill's podcast (h/t CBS Sports' Jared Dubin).

This breakup was as swift as it was stunning.

"He is no longer a Buc," then-head coach Bruce Arians said after Tampa's win over New York, per ESPN's Jenna Laine. "That's the end of the story."

3. The Steelers and Le'Veon Bell

AP Photo/Michael Wyke

Le'Veon Bell was a standout running back during his five seasons with the Pittsburgh Steelers. He made three Pro Bowls and tallied just under 8,000 scrimmage yards with the franchise before things went south during the 2018 offseason.

In March of 2018, the Steelers made it clear that they'd be giving Bell the franchise tag for the second consecutive offseason. That decision came after Bell made it clear that he didn't want to play without a multi-year agreement.

"I'm not going to settle for anything," Bell said, per ESPN's Jeremy Fowler. "I know what I do and what I bring to the table. I'm not going out here getting the ball 400 times if I'm not getting what I feel I'm valued at."

After initially indicating to fans on social media that he would play on the tag in 2018, Bell reversed course and never reported to the Steelers. His holdout lasted well into the regular season, and with James Conner proving to be a quality replacement, the Steelers never appeared eager to bring Bell back into the fold.

"So be it," coach Mike Tomlin said when asked what would happen if Bell never returned, per Fowler.

Bell never did report to the Steelers in 2018, and he signed with the Jets as a free agent the following offseason. It was an overall messy situation because it hung over Pittsburgh throughout the season, and it wasted a prime year of a running back who, at the time, was considered one of the best in the league.

2. The Texans and Deshaun Watson

AP Photo/Kamil Krzaczynski

Lengthy disputes that turned into missed seasons are always messy. The Steelers experienced that with Bell in 2018, but they still salvaged a nine-win season.

When quarterback Deshaun Watson refused to play for the Houston Texans in 2021, it led to a four-win season, the firing of head coach David Culley, and the unexpected fall of an up-and-coming star.

Watson had reached the Pro Bowl in three of his first four seasons, and he led the league in passing yards in 2020. Despite agreeing to a contract extension in 2020, however, Watson requested a trade one year later.

According to ESPN's Adam Schefter, Watson had simply become fed up with Houston's direction and the way the franchise chose to operate:

"The Texans did not inform Watson that they intended to hire [GM Nick] Caserio, and he found out about the hire Tuesday on social media. ...Last offseason, Houston didn't let Watson know that star wide receiver DeAndre Hopkins would be traded, which led to some disappointment. Now that it has happened again, Watson is said to be infinitely more bothered, sources told ESPN."

By February 2021, Watson had informed Culley that he had "no intention of suiting up for the team again," according to ESPN's Dan Graziano.

Watson didn't, and he stayed away for a full year while also facing multiple allegations of sexual assault and misconduct. The NFL suspended him for 11 games and fined him $5 million, though two grand juries declined to pursue criminal charges. He was dealt to the Cleveland Browns in 2022—a parting that has worked out well for Houston in retrospect while being a total flop for both Watson and Cleveland.

1. The Eagles and Terrell Owens

AP Photo/Bill Kostroun

Some NFL breakups are messy. Others are downright spiteful. Terrell Owens' split from the Eagles in 2006 fell into the latter category.

Owens' first season with Philadelphia went almost as well as it could have. He had a 1,200-yard season, and the Eagles reached Super Bowl XXXIX. Despite playing with a broken leg in that game, Owens still tallied nine catches for 122 yards—though Philly fell short in a 24-21 loss to the New England Patriots.

The following offseason, though, Owens demanded a new contract from the Eagles, and at one point, he was sent home following a heated argument with head coach Andy Reid.

That preceded Owens' now-infamous driveway interview.

The acrimony carried into the 2005 season. Owens got into a fight with former teammate and Eagles ambassador Hugh Douglas in November. He appeared to criticize quarterback Donovan McNabb in an ESPN interview just days after the fight, while openly criticizing the Eagles for not making a bigger deal about his 100th career touchdown. Following the interview, the Eagles suspended Owens indefinitely.

"There's an accumulation of events culminating with a series of things last week, including the very public interview that he did," then-Eagles president Joe Banner said in a news conference. "I think there's a long list of things, some of which you know about and some of which aren't public."

The Eagles rejected a public apology from Owens, and he never again played a down for the franchise. He signed with the rival Dallas Cowboys in 2006, and he remained critical of his relationship with the Eagles years later.

"I think everyone sees and knows that it really wasn't my fault," Owens told 97.5 The Fanatic in 2016 (h/t Ryan Wilson of CBS Sports). "Donovan was their guy. I was pretty much the scapegoat."

Considering how things ended for T.O. and the Eagles, Philly's split with Brown almost seems amicable.