Teams Athletes Seriously Regret Signing With

A number of sports signings have made headlines in the past for an array of reasons. Jalen Hurts' five-year $255 million extension contract with the Philadelphia Eagles was reportedly the first of its kind, "The Messi Effect" brought big business after the soccer star's move to Inter Miami CF, and LeBron James' $205 million contract with the Lakers put him on a fast track to reaching billionaire status.

Although many athletes are often delighted to conquer newer grounds, some moves don't turn out successful. Tampa Bay Buccaneers wide receiver Antonio Brown had his contract terminated in January 2022 following a reported disagreement with the team over an ankle injury. Brown's exit came months after he'd re-signed with the Buccaneers. On a more mutual front, Austin FC and Paraguayan soccer player Cecilio Domínguez cut ties amicably in July 2022. The announcement of his departure was after an earlier suspension regarding a domestic violence incident.

While many athletes often express joy after closing a new deal, the same cannot be said when things go south. Regrets are rarely made public — however, these players did make their displeasure known, citing circumstances such as sudden trades, uninspiring teammates, and the good old desire to follow the money. Keep reading to find out which teams these athletes would have kept out of their resumés.

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Mitch Trubisky's contract with the Steelers 'happened too quick'

When backup QB Mitch Trubisky closed a two-year deal with the Pittsburgh Steelers in March 2022, he expressed how satisfied he was with his choice. "When we found out Pittsburgh had interest, I talked to my agent and said this is where I want to be," Trubisky, who'd been in the NFL for five years by that time, said.

Even though the then-free agent seemed content, he'd sing a different tune less than a year into his contract. Trubisky felt that the choice to go with the Steelers was abrupt. "I didn't really have a long time to think of the decision. I wish I would've taken some more time and not just signed the first day of free agency," he shared with ESPN. The former Chicago Bears quarterback added that he ought to have conducted proper research and consideration before signing the contract. 

However, his run with the team continues, as of this writing. During a May 2023 appearance on "The Pat McAfee Show," Steelers' general manager Omar Khan revealed that Trubisky had wrapped up an extension agreement that will see him commit to the six-time Super Bowl champions for another two years.

Jamaal Charles got tired of the bench

Running Back Jamaal Charles was let go from the Kansas City Chiefs in February 2017, nearly a decade after his April 2008 pick. Although Charles' career was threatened by several injuries, his NFL legacy appeared to be on the right track when he signed a reported one-year contract with the Denver Broncos later that year. Charles' signing was crowned with a welcoming tweet from ex-Broncos-player-turned-consultant John Elway.

However, being continually benched as the season progressed would eventually lead Charles to regard the position as a dead-end. Charles voiced his frustrations with the Broncos, according to The Denver Post. "I ain't playing," he said discontentedly, citing his skills as visibly underutilized. "No reason for me to just sit around and look at people play."

Although he showed support for his fellow teammates, Charles was seriously considering shopping elsewhere. "At the end of the day, I just got to see what's the future for me. That's the next step," he commented. In October 2018, Charles made a year-long commitment to play for the Jacksonville Jaguars. It was his shortest deal yet, one that only lasted two games.

Dwyane Wade wanted more time with the Cleveland Cavaliers

The better part of Dwyane Wade's NBA career was spent with the Miami Heat. Wade's first and only long-term run with the Heat ended in 2016 when he agreed to move to the Chicago Bulls for two years. It was a nerve-wracking move that gave him many sleepless nights, as he shared on "Live with Kelly."

He later signed with the Cleveland Cavaliers for one year, a move that made for a wholesome reunion with his ex-Heat teammate, LeBron James. Unsurprisingly, James had persuaded Wade to join him. Wade's stint with the Cavaliers was cut short in a February 2018 trade, which was endorsed by James through an Instagram post. Wade's destination: Miami Heat, where his career began. Only later that year did he share his discontent with the trade.

"If I had known that was gonna happen, I wouldn't have signed there," the three-time NBA champion remarked in a chat with The Athletic. "It's gonna be an item on my resumé that's hard to understand, but it happened." Regardless, the three-time NBA champion was confident that he paid his dues and established good connections during his time with the Cavaliers.

Lionel Messi's two-season stint at PSG was unwanted

Since his early teens, Lionel Messi called FC Barcelona home. His departure from the team in 2021 was therefore emotional — not only for the one-time World Cup winner, but for his devout fanbase as well. In his farewell speech, a teary-eyed Messi highlighted that the principles he'd acquired at Barcelona FC were all part of his legacy. Additionally, the star soccer player mentioned that he and his family would have preferred to remain in Spain.

What followed was a two-year run at Paris Saint-Germain, one which was tumultuous at best and highly criticized by PSG fans, such as ex-winger Jérôme Rothen. After moving to Inter Miami CF in July 2023, Messi shared that the decision to move to PSG wasn't desired. Speaking at his inaugural press conference, he said (as translated by The Athletic), "When I left for Paris it was something that I didn't want to do. I didn't want to leave Barcelona. That was a last-minute decision." Finding a footing away from all he knew since childhood, he added, was a herculean task. Unlike Paris, however, adjusting to life in Miami had been a much easier transition.

Pablo Sandoval wished he'd chosen the Giants over the Boston Red Sox

In 2014, third-baseman Pablo Sandoval declined a three-year, $40 million extension deal with the San Francisco Giants to instead agree on a multi-year deal with the Boston Red Sox. In a since-deleted Instagram post, Sandoval shared in part that the end of his relationship with the Giants — the team he was with when he was named the 2012 World Series MVP— was an individual choice inspired by the need to take on a more challenging course. In an interview with Bleacher Report, Sandoval divulged that his exit from the Giants was a long time coming and that he didn't like how the team was treating him. "I knew early in spring training last year I was going to leave," he said. "They didn't respect my agent. Contract talks, everything. The way Brian Sabean (Giants' general manager) talked to my agent."

As it turned out, the Red Sox were a risky bet. Sandoval struggled to measure up to his $95 million contract and finally parted ways with the team in 2017. Speaking to GQ, Sandoval mentioned that he should have taken the Giants' offer. "I should have stayed. I know. I learned my lesson," he told the publication. "But I'm happy I went through it, man, because I kept my eyes open and learned a lot of things." Baseball's beloved "Kung Fu Panda" later rekindled his bond with the Giants, and just as loud as his dismissal of the team had been, he offered a heartfelt written apology.

Scottie Pippen's Houston Rockets dream hit a wall

Scottie Pippen may have helped the Chicago Bulls bag six championships during the first 11 seasons he played with the team, but it wasn't enough to revise his contract. In 1991, Pippen signed a five-year $18 million extension deal with the team that was highlighted in Michael Jordan's "The Last Dance" as a particularly bad contract. A dispute ensued between Pippen and Bulls' general manager Jerry Krause. Pippen equally had resentment toward Bulls' team owner Jerry Reinsdorf.

In January 1999, Pippen was finally traded from the Bulls to the Houston Rockets in a reported $67 million deal. He was meant to be part of a power team headlined by himself, power forward Charles Barkley, and Hakeem Olajuwon. Pippen had every intention to add a seventh ring, according to a conversation he had with NBC at the time. "It [the move] gives me the opportunity to still contend for a championship and that was the most important thing that I looked at when I made my move out of Chicago," he said.

Pippen's ambitions proved to be a pipe dream that started a years-long feud with Barkley. "We just didn't have the right chemistry," he revealed in an interview with Sirius XM. "We were aging a little bit ... I didn't realize how much Hakeem had diminished in the game, I'mma be honest. And I didn't realize Charles wasn't as dedicated as I thought he would be." Pippen only lasted a season with the Rockets and afterward joined the Portland Trail Blazers.

DeMarcus Cousins would have 'skipped my Sacramento Kings draft workout'

DeMarcus Cousins re-signed with the Sacramento Kings for a reported $62 million in 2013. Kings owner Vivek Ranadive told ESPN that Cousins' retention was commercially beneficial. "I'm just doing what I do in my business every day, just betting on the best. And he represents the best," he stated. 

Although the Kings had stood their ground that Cousins' position with the team was still intact in 2017, they eventually went back on their word and traded him to the New Orleans Pelicans in the company of former Israeli small forward Omri Casspi. Word on the street was that Ranadive banked on the potential of Pelicans' Buddy Hield, whom he acquired alongside Tyreke Evans and Langston Galloway.

In a chat with Andscape, Cousins expressed that he stayed longer with the Kings than he should have. "My biggest regret is not leaving when I had the chance," he told the publication. "I had the chance, but I fought it. I had the chance to leave, but I didn't." The Guaynabo Mets center further hinted that he brought more to the table in his partnership with the Kings in yet another interview with Andscape, saying, "I would've skipped my draft workout [in Sacramento] ... What did Sac do for me? Besides say my name [draft day]. I did more for them than they did for me. That's just being honest."

Jerry Stackhouse 'felt like a better player' than Michael Jordan

Long before he was the Vanderbilt Commodores head coach, Jerry Stackhouse was playing for the Detroit Pistons. In September 2002, Stackhouse received the news that he'd been traded to the Washington Wizards — three weeks after a gym session with Michael Jordan. Stackhouse wasn't impressed. "I'm just disappointed ... because I have to leave my home," he said to the Associated Press. "It's not easy, but at the same time it comes with this business and I understand that."

Although he'd pointed toward a contract renegotiation with the Pistons, Stackhouse knew a trade was possible. At the very least, he expected to move to the Miami Heat or the Portland Trail Blazers, as he shared in an interview with The Washington Post. Regardless, Stackhouse took to the court with Jordan, who'd stepped out of retirement for a second time to play for Washington.

In an unfortunate turn of events, Stackhouse found that he had placed Jordan on a pedestal, one which the six-time NBA champion fell off of when they became teammates. As such, he would have preferred not to have been a Wizard altogether. "Honestly, I wish I never played in Washington for a number of reasons," Stackhouse reflected during an interview with The Woj Pod. "I felt like we were on our way in Detroit before I got traded there, but it was just ... really challenging to be in a situation [with] an idol who at this particular point, I felt like I was a better player and things were still being run through Michael Jordan."

Michael Jordan regretted coming out of retirement

While Jerry Stackhouse was doubting his involvement with the Wizards, his idol, Michael Jordan, had some questions of his own. Jordan's September 2001 move had done rounds unofficially before it was formally confirmed. "I feel there is no better way of teaching young players than to be on the court with them as a fellow player, not just in practice, but in NBA game," he said, per The Washington Post

To return as a player, the A-list basketball star had to give up his post as the team's president of operations and put his 10% share of the Wizards up for sale. Fast approaching 40, Jordan had the difficult task of leading the Wizards to their second championship.

Although he would later maintain that he gave the opportunity his best, in an interview with Cigar Aficionado Jordan revealed that the choice to ditch management for the court was ill-advised. "One of the bad decisions I made was to go back and play," Jordan shared. " Even though I was soothing an itch that I had, I also thought I was being innovative in my job by going down and evaluating the talent firsthand."

Alex Rodriguez would have preferred to play for the Mets

In December 2000, Alex Rodriguez transcended sports signing heights when he secured a reported 10-year $252 million deal with the Texas Rangers that guaranteed a $10 million onboarding bonus spread across his first five years. "It's an extraordinary contract for an extraordinary player," the New York Mets' then-general manager Steve Phillips said when the announcement was made, per SFGATE

Unknown to him, the shortstop's heart was with the Mets. "I went for the contract when my true desire was to go play for the Mets," Rodriguez said in an interview with the New York Daily News (via Deadspin). Rodriguez would have had a chance with the Mets, in fact, were it not for requests he put forward through his agent Scott Boras that made them opt out. He asked for his own office, a promotions team, a stand at spring training, a luxury box, private air transport, and a ton of billboards, according to ESPN.

Following the tumultuous relationship he had with the Rangers, Rodriguez was careful not to repeat the same mistake with the Yankees. "To make the right decision just feels really good," he told the New York Daily News. "Versus being taken down a road where I'm like, 'Oh, my God, where am I? Oh, $400 million to play in some place I hate? Great, I'll blow my f*** head off.'" Rodriguez's Mets dream nearly came full circle when he was a contender for the team's purchase in 2020.

Shaquille O'Neal 'would have stayed' with the Orlando Magic

Shaquille O'Neal got his start with the Orlando Magic in 1992 in a reported seven-year deal worth $40 million. Four years went by and O'Neal became a free agent. Both the Magic and the Los Angeles Lakers fought to sign him, and in the end, O'Neal inked a presumed $120 million contract. His upbringing in a military household played a part in his final choice, and so did the Lakers' legacy. "Change is for the good," O'Neal said at a press conference, via ESPN. "I'm a military child, so I'm used to relocating every, you know, three or four years and the Lakers have a great tradition."

O'Neal spent eight seasons with the Lakers, which included a three-championship winning streak. His trade to the Miami Heat afterward was rumored to have been because of an existing feud with his fellow Laker Kobe Bryant, one which was further fueled when O'Neal told reporters he was in the South Florida city to find a home in a team. O'Neal would eventually vow to make a life change after Bryant's death.

When he was inducted into the Orlando Magic Hall of Fame long after retirement, O'Neal looked back at his exit remorsefully."I regret it sometimes." he shared. "If I had known what I know now, I would have stayed. I would have stayed and fulfilled my seven years and then looked at it differently after my seventh year." 

Jason Kidd doubted his decision to stay with the Nets

Jason Kidd often wondered what it would have been like to play alongside Tim Duncan, whom he spoke so highly of in a conversation with ESPN. The catch was, he would have actually been able to make it happen if he made a different choice in 2003. Kidd and the San Antonio Spurs had reached an agreement he turned his back on, one which would haunt him.

"The biggest disappointment is maybe not joining them [San Antonio] and trying to win a championship when I had the opportunity of becoming a free agent," he admitted. "I thought I was going to be a Spur and I committed when I was down there on my visit and on the flight home I think I got cold feet."

The then-point guard renewed his bond with the New Jersey Nets in a six-year $103 million deal. At the time, he pointed out that becoming a Spur would have been an effortless transition, but he had a mission to get a ring with the Nets. Unfortunately, Kidd got his only ring after 17 grueling years — as a Maverick.