The Most Bitter Exits in Sports

It happens to the best of us.

As fans, we invest so much of ourselves in our favorite players and coaches. We purchase their jerseys and wear them with pride. We spend every second of our free time (and some of our on-the-clock time) reading about their exploits. We become deeply invested in their favorite foods/pets’ lives/opinions on The Amazing Race.

And then, their contracts end and they leave us. They leave us, our favorite team, our city, and we’re left with nothing except bitter hatred and a jersey to burn.

Here’s a look at some of the most bitter exits in sports.

20. Adam Vinatieri and the New England Patriots

It always hurts the most when a playoff savior who delivers a championship to your team defects to one of your team’s biggest rivals. That’s what happened with Adam Vinatieri.

He may be a kicker, but he will forever be one of the most storied characters in New England Patriots lore after his fearless performances in the postseason, especially in the infamous Snow Bowl/Tuck Rule Game in 2001, when his overtime field goal allowed the Patriots to continue their quest for the Super Bowl.

Vinatieri gave the Patriots the kind of weapon any team would have loved to have: a kicker who could seemingly make any field goal, from anywhere on the field, at any time. He was a valuable commodity, and it showed when the Indianapolis Colts—who had become one of New England’s biggest rivals during the Peyton Manning/Tom Brady era—plucked him away in 2006.

Watching Vinatieri finish off Manning’s drives instead of Brady’s is not something Patriots fans ever wanted or expected to do, and they have never forgiven Vinatieri for his defection.

19. Pacman Jones and the Tennessee Titans

Sometimes, no matter how much you want a heralded prospect to succeed, it just doesn’t happen. Ever.

Such was the case with Adam “Pacman” Jones and the Tennessee Titans, who drafted him with the sixth overall pick of the 2005 draft. The cornerback was supposed to be a game-changer. He was supposed to turn the Titans into a defensive beast. But he never really got a chance to have an impact at all because of off-the-field problems and injuries.

According to NFL.com’s Mark Sessler, Jones’ stats in two seasons with the Titans amounted to four punts returned for touchdowns, and he has been arrested at least six times since 2006. He was suspended for the 2007 season because of off-the-field issues, and once he returned to the league, it was with Dallas, not Tennessee. So much for those great expectations.

The numerous ways in which he disappointed the Titans faithful aren’t lost on Jones. He admitted to being young and distracted while with Tennessee, and when asked in a 2011 interview whether he expected a warm reception upon returning to LP Field, he told Pro Football Talk’s Michael David Smith:

"

Hell no fans aren’t going to give me a good ovation. They booed me when I was there, so you know they are going to boo me when I’m on the other team. But I don’t care. That [expletive] don’t bother me.

"

18. Donovan McNabb and the Philadelphia Eagles

It was hard to avoid feeling bad for Donovan McNabb during the latter part of his doomed career with the Philadelphia Eagles. In the beginning, he showed so much promise—and perhaps that is to blame for the way things ended for him.

Perhaps expectations for him were just too great.

Perhaps he was doomed from the start, when Eagles fans made it clear they did not approve of the front office’s decision to draft him (see above). 

McNabb spent 11 seasons quarterbacking the Eagles, and he had great records in five of those seasons. Unfortunately, he also had quite a few awful seasons, plus all of the injuries—one of which came directly after he signed a ginormous 12-year, $115-million deal. Fans hated watching him fail in big games during the playoffs, and his teammates were sick of his excuses for those failures.

Needless to say, his time in Philly ended abruptly in 2010, when he was traded to Washington and Michael Vick took over for good.

Was McNabb a bad quarterback? No. There are plenty of decent quarterbacks who fail to win rings. Did his output ever match his reputation, though? Not at all. And that’s why it was so infuriating for fans to watch him for all of those years.

17. Jay Cutler and the Denver Broncos

Poor Jay Cutler.

He just can’t win, and his struggles with the fans and the media started long before he arrived in Chicago. It was all downhill for Cutler and the Denver Broncos after Cutler found out that new coach Josh McDaniels had attempted to bring in Matt Cassel, and once he found out his new coach was interested in replacing him before even giving him a fair shot, it was all over for Cutler in Denver.

When the Broncos dispatched him to Chicago in exchange for Kyle Orton and draft picks in 2009, nobody was all that sad to see him go. He failed to achieve much success with Denver, going 17-20 as a starter.

The fans may not have been too disappointed to see him go, but they certainly wish he would have made a bit more effort to be a pleasant face of the franchise during his three years there. Plus, come on. It’s professional sports. There are always trade rumors swirling around, and no player should take them personally.

It wasn’t only the fans who seemed skeptical about Cutler’s ability as a teammate and as a leader. Upon hearing the news of the Cutler trade back in 2009, Brian Urlacher told The Chicago Tribune, via ESPN.com:

"

I guess the Bears felt like we needed another quarterback, so they made a move. They gave up a lot. Cutler must be pretty good...I will say this: I think Kyle Orton is a good quarterback. He's a great teammate. I hope he does really well in Denver.

"

16. Urban Meyer and the Florida Gators

So he’s not a player—he’s a coach—but still, his exit from the University of Florida remains one of the more bitter departures in the NCAA.

Urban Meyer created a monster with the Gators. He led the football team to national championships in 2006 and in 2008, and during his tenure, he compiled a 64-15 record. Florida was always scary with Meyer at the helm. It was always a threat—until 2010, when it went 7-5. And right after that disappointing season is when Meyer chose to walk away, only to pop up a couple of years later at the helm of another premiere program: Ohio State.

At the time of his resignation, according to AOLNews.com’s Jim Henry, Meyer cited a desire “to focus on his family and his life outside of football.” Apparently, that’s a nice way of saying, I’m done with you, Florida, because Ohio State is way cooler and I went there.

15. Peyton Manning and the Indianapolis Colts

Outwardly, this wasn’t a contentious divorce. It seemed pretty amicable.

Peyton Manning was the face, the heart and the soul of the Indianapolis Colts from the moment they drafted him with the first overall pick back in 1998. He turned this team into a perennial competitor and delivered a championship ring in Super Bowl XLI, which also was Indy’s first trip to the big game since 1970.

When Manning went down with a neck injury that caused him to miss the entire 2011 season, though, the writing was on the wall, and everyone knew it. It was time for a change, and Manning would soon be on his way out in favor of 2012 first-round draft pick Andrew Luck.

Manning, admirably, was a gentleman about the fact that the team he built decided to treat him like soap scum instead of one of the best quarterbacks in NFL history.

Yes, football is a business, but there are a few cases in which loyalty is necessary. And after what he did for this franchise, Manning deserved a little support.

As I love to point out, this is a man who wouldn’t talk to his little brother for a week when they were kids because young Eli beat him in a backyard football game. He is one of the most competitive people on the planet. So therefore, anyone who thinks it wouldn’t give Manning immense pleasure to stick it to the Colts by dominating with the Broncos this season is crazy.

14. Alex Rodriguez and the Texas Rangers

He’s one of the most polarizing players in the history of sports, and no matter what he says or does, someone is always on his case.  

For a long time, A-Rod was heralded as the most talented shortstop in baseball. For a long time, he even seemed like a nice guy. That all changed when he was traded from Texas to New York in 2004.

The Rangers would have loved to hold on to their superstar—who, in three years in Arlington, hit .305 with 156 homers and 395 RBIs—but they were financially handcuffed. They needed to move some payroll, and A-Rod—and the $179 million remaining on his $252 million contract—was the best option. 

It’s not A-Rod’s fault that the Rangers decided to pay him so much only to later decide they couldn’t/didn’t want to keep him. And Texas has certainly recovered pretty nicely over the last several seasons.

But fans, apparently, are still unwilling to let their sour feelings toward their former hero subside. According to a 2011 poll conducted by The Dallas Morning News, A-Rod was deemed the No. 1 Rangers character fans love to hate. 

13. Jeremy Lin and the New York Knicks

Jeremy Lin’s time with the New York Knicks was short and befuddling, but unlike many of the others on this list, Lin is one of the most likable players in his league. So how did this happen?

Lin earned a lot of fans in New York last year when he stepped in as the Knicks’ backup point guard and helped them reel off seven straight wins in February. He became an unlikely hero and beloved fan favorite, even after going down with an injury that kept him out for the final month of the season and for the Knicks’ short-lived trip to the postseason. 

Then, things got weird.

First, the Knicks started giving the impression that they weren’t 100 percent buying into the Lin hype. Then, Lin—a restricted free agent—signed an offer sheet with the Houston Rockets that would pay him $28.8 million over four years. Maybe Lin assumed the Knicks would match it. Maybe the Knicks didn’t think Lin would consider signing an offer sheet before conferring with them.

Whatever the case, there was some kind of miscommunication. As a result, the Knicks couldn’t—and didn’t—match. Lin, shockingly, became a Rocket.

There certainly seemed to be some hard feelings on the part of the Knicks after Lin skipped town, but if anything, fans are mad at the franchise that they were forced to bid farewell to their new fave after getting only a couple of months to enjoy him. 

12. Eli Manning and the San Diego Chargers

Way back when, when he was just The Other Manning, Eli gifted us with one of the most hilarious awkward moments in NFL draft history. 

Manning’s tenure with the San Diego Chargers was short. So short, in fact, that it does not even appear on his stat line at any point. Back then, there wasn’t much Manning knew about the NFL, but he did know one thing.

He didn’t want to play for the Chargers.

The problem was, Manning was the best quarterback prospect on the board, and the Chargers had the No. 1 pick. 

Manning told the Chargers he wanted nothing to do with them, and they selected him anyway—only to trade him to New York minutes later in exchange for the No. 4 overall selection, Philip Rivers. But that moment when Manning had to stand up on the podium holding that Chargers jersey and attempt to smile is an image that gave all of us a giggle for many years to come.

Except San Diego fans.

No fans want to hear from the first overall selection in the draft that their team isn't good enough. And these days, they may be bitterly wondering what life would have been like with the two-time Super Bowl champion under center instead of Rivers.  

11. Terrell Owens and the Philadelphia Eagles

Terrell Owens wasn’t the first wide receiver in the NFL to show tremendous promise on the field and tremendous warning signs off it. A wideout like T.O. was one Philly felt blessed to have—at first—because his skill was so scintillating.

In his first year with the Eagles in 2004, Owens registered 1,195 yards and 14 touchdowns to help them earn a trip to the Super Bowl (where they eventually lost to New England), battling injuries in the process to be able to stay on the field and help his team. 

In 2005, the honeymoon ended. Bright and early, T.O. was suspended for a week in training camp for swearing at head coach Andy Reid, and the suspensions didn’t end there. In November, T.O. was suspended for four games and was deactivated for the rest of the season due to what Reid called “a large number of situations that accumulated over a long period of time,” according to ESPN.com.

After his first season in Philly, Eagles fans got a look at what could have been. It looked like Owens had something really good going. He looked like he had promise. But it didn’t take long at all for that illusion to be shattered, and Eagles fans haven't forgotten about it. 

10. Pedro Martinez and the Boston Red Sox

This exit is particularly infamous because of an instance that occurred just weeks before the player in question skipped town. While the Boston Red Sox were in the midst of a bitter playoff race against the New York Yankees—while they were attempting to win their first World Series in 86 years—Pedro Martinez was asked in a postgame news conference whether he’d leave the Red Sox as a free agent in the offseason. He said no. 

Then, just a few weeks later, he was crowned the newest member of the New York Mets. 

Granted, it wasn’t all Pedro’s fault. Theo Epstein didn’t believe the ace was worth the four-year deal he was asking for, and Theo was right. Pedro’s effectiveness on the mound plummeted after just two years.

But the Red Sox wouldn’t have been able to defeat the Curse of the Bambino without Pedro. He faded into the background a bit given the arrival of Curt Schilling, but when Boston needed him to be lights-out in the postseason against the Yankees, he was just that.

He was also a big part of one of the most infamous moments in Red Sox history (see above), for better or worse. He was one of those players Red Sox fans expected to be around forever.

Also, World Series aside, watching one of the best pitchers in the history of the franchise skip town is never easy for the fans. 

9. Brett Favre and the Green Bay Packers

Like Manning, Brett Favre built the Green Bay Packers into a machine. But unlike Manning, he spent far too long toying around with the organization he built, and it got tired—fast. 

Favre spent 16 years with the Packers. He brought them Super Bowl XXXI. For a long time, he was the most beloved figure in the history of the city. And then all the retirement nonsense began. 

Each offseason from about 2006 onward, Favre took his sweet time deliberating between giving it another season and embarking on a permanent vacation from the league. That meant the Packers often had to wait months after the season ended for word on whether or not they’d have their star quarterback in the fold, or whether they’d have to pursue other options.

Just in case they needed him, Green Bay drafted a guy named Aaron Rodgers in 2005. Rodgers, like the Packers, never really knew when—if ever—he’d be getting his shot instead of sitting on the bench in favor of Favre. (That lowly backup, of course, would go on to lead the Packers to a Super Bowl victory in 2010.)

Finally, in 2008, Favre decided enough was enough. He retired. Just kidding! He cropped up a few months after “retiring” as a member of the New York Jets. And everyone in Green Bay and beyond responded with a sigh and a half-hearted eye-roll. 

8. Eric Mangini and the New England Patriots

This is another one that is coach-centric instead of player-centric, but any time a handshake between two coaches becomes must-watch TV, you know the story behind it must be good. 

Eric Mangini, of course, was one of Patriots coach Bill Belichick’s prized disciples. Mangini served under Belichick for nine years and was on Belichick’s coaching staff for all three of the Patriots’ Super Bowl victories. As Regina George would say, Belichick made Mangini.

And then, the defensive coordinator made a couple of faux pas. He finally left the Patriots in 2006 to replace Herm Edwards as the head coach of the New York Jets, the Patriots’ chief division rival. But more importantly, he is widely regarded as one of the informants who was instrumental in bringing the Spygate scandal to light. 

Since then, Mangini expressed substantial regret over the way he handled things in light of the way his relationship with Belichick has disintegrated. That, of course, could be partly due to the way his head coaching career has panned out.

Hint: It didn't go well. 

In 2011, Mangini told WEEI, via ESPNNewYork.com’s Richi Cimini:

"

It's one of those things where the end result wasn't the goal. I owe so much to Bill. I appreciate what he's done for me and my intention was never to hurt him or the [Patriots] organization, the Kraft family. Yeah, there's a lot of regrets, I didn't want to hurt him or the Patriots by any stretch.

"

You can apologize all you want, Mangini, but throwing your mentor under the bus? Not cool.

Clearly, Belichick has always held a grudge, judging by the way that he often embarked upon his postgame handshakes with Mangini as though he were afraid of catching something. 

7. Carmelo Anthony and the Denver Nuggets

Like so many top-tier draft picks that ended up with non-huge-market teams, it didn’t take long for Carmelo Anthony to tire of the Denver Nuggets.

Denver drafted him in 2003 with the third overall pick, and for the next seven-plus seasons, he helped the Nuggets become a contender. But it appears that the Nuggets weren’t competitive enough for Carmelo’s tastes. Although they went to the playoffs for seven straight seasons with Carmelo and had the talent to do some damage, they only advanced past the first round once. 

Fans were surprised that Carmelo didn’t seem to have any intention of signing an extension with the Nuggets or sticking around for the near future. The franchise player was making it clear he wanted out in favor of a big-market team. Just in case there was any confusion, his agent told the team to “do itself a favor and trade him” in 2010, according to Yahoo!’s Adrian Wojnarowski. The Nuggets met his demand shortly thereafter, sending him to New York. 

No fan ever wants to see the franchise player express so little interest in sticking around with the team he helped build. But in Carmelo’s defense, at least he didn’t announce his trade in a prime-time television special on ESPN. 

6. Manny Ramirez and the Boston Red Sox

Manny Ramirez went from one of the most beloved characters in Red Sox history to the most hated in record time.

Like so many others on this list (I'm sensing a pattern—why are superstars so eager to leave Boston), Manny was one of the poster boys of the “idiot” Red Sox team that won it all in 2004, when he was the Series MVP.

He was also critical to Boston’s 2007 win and, for a while, was regarded as the scariest right-handed hitter of this generation. Even his strange habits—failing to show up for team pictures, keeping a bottle of water in his back pocket while playing left field, cutting off throws to the cutoff man (see above)—were met with adoration from those in Red Sox Nation. 

That is, until 2008, when he appeared to be mailing it in. His relationship with the Red Sox—with his teammates, the coaching staff, the front office—quickly eroded, mostly due to off-the-field issues and a perceived lack of effort. In the waning minutes of that year’s trade deadline, he was shipped off to the Los Angeles Dodgers, and Fenway Park said a bitter farewell to one of the greatest sluggers to ever grace its green pastures. 

I will also take this opportunity to direct you to Bill Simmons’ post-trade epic analysis of the enigma that is Manny Ramirez. A must-read. 

5. Ron Artest and the Indiana Pacers

Ron Artest has been nothing if not polarizing during his career. He’s been a part of some high high's—he won a title with the Lakers in 2010—and some low low’s. (Malice at the Palace, anyone?) Though he seems to have reformed to some degree these days, his roughest moments came during the five seasons he spent with the Indiana Pacers. 

Even Artest makes no bones about the fact that perhaps he wasn’t at his best while he was with the Pacers, telling CBSSports.com’s Ken Berger that he regrets “bailing out on that Pacer team.” He’s talking about the aftermath of his 73-game suspension stemming from the infamous brawl with the Detroit Pistons, in which he was adamant about his desire to be traded. 

Artest told Berger:

"

I mean, outside not going to church every single Sunday, bailing out on that Pacer team is my biggest regret. Every time I see Jermaine, every time I see Steve [Jackson] and Jamaal [Tinsley]...I get a little bit of a feeling when I see Bird, because he was such a great player and I respect him so much. So I get that feeling when I see Bird. I feel like a coward. I feel like I don't even belong in their presence, really.

"

Well, at least Artest is apologizing. Sort of. He gets credit for that. But he'll still be remembered in Indiana for being a part of one of the lowest moments in franchise history. 

4. Babe Ruth and the Boston Red Sox

This is perhaps the most bitter exit in the history of sports, but in light of the fact that the Curse of the Bambino has since been broken—and that it's been almost 100 years—it has faded into the background. Still, this was the trade that set the tragic tone for the Red Sox for the greater part of the 20th century. 

The Red Sox and the Yankees didn't always hate each other—at least not as much as they did after Babe Ruth was sold from Boston to New York on Jan. 3, 1920.

Prior to the trade, Boston was the best team in baseball, winning five of the first 15 World Series, and Ruth was the best player in the game. But according to folklore, Red Sox owner Harry Frazee needed the money from the sale of Ruth to finance an ill-fated musical. 

And we all know what happened after that.

The Yankees went on to become the most feared team in baseball, while the Red Sox would not only fail to win a championship for 86 years—they would lose in the most excruciating ways.

Yankees fans would taunt the Red Sox and their fans with chants of "1918"—the year of Boston's most recent title—up until 2004, when the supposed curse was broken. 

3. Ray Allen and the Boston Celtics

The end began for Ray Allen and the Boston Celtics long before it came in July 2012. The star shooting guard—who was once beloved for helping to deliver banner No. 17 to Boston in 2008 as part of the Celtics' revamped Big Three—went down with an injury during the 2011-12 season, and Avery Bradley took his place in the starting lineup.

Even when Allen was healthy enough to return, he discovered that Bradley was Option Numero Uno. Plus, he was still smarting over trade talks that had cropped up earlier in the season. 

And so, after the Celtics were bounced from the playoffs by the Miami Heat, Allen aligned with the enemy, turning down a more lucrative offer from the Celtics to join LeBron James & Co.

It’s bad enough that Allen ditched the Celtics—whom he spent five years with—in favor of the hated Heat. It’s worse that he turned down more money and, allegedly, a no-trade clause, because he was so eager to ditch the Green. But the worst part is he seems to care more about his own stat line and his ego than helping his team win. He wanted more touches, he wanted more starts, even if it was Bradley’s time to shine. 

It’s one thing to join the enemy for more money and a better offer. It’s another to do what Ray did. Can you blame KG for giving him the cold shoulder? 

2. Dwight Howard and the Orlando Magic

For the last several years, Dwight Howard never seemed to be happy with the Orlando Magic. The team drafted him with the first overall pick in 2004, and though it often seemed to be on the verge of a championship in the ensuing eight seasons, it never quite got there.

And once Howard realized he wasn’t going to win a ring with the Magic—not with the Big Threes in Miami and Boston dominating the Eastern Conference—he made his feelings clear. He wanted out. 

Or did he? It changed daily. 

In one of the most annoyingly dragged-out personnel moves ever, Howard—whose departure from Orlando had been rumored to be imminent for months—was traded to the Los Angeles Lakers in August 2012. Casualties of his departure included coach Stan Van Gundy—who, rumor has it, was fired at season’s end after Howard spent the second half of 2012 begging the front office to dispose of him—and a Magic team that is lost without its superstar center. 

1. LeBron James and the Cleveland Cavaliers

The biggest betrayal of them all occurred on the evening of July 8, 2010. As sports fans, we all remember where we were the moment LeBron James told the world he was taking his talents to South Beach. 

After he spent seven years with his hometown Cleveland Cavaliers, his fans were hoping that LeBron would show some loyalty once he became a free agent in 2010. They were hoping that he’d put his faith in the organization. That he’d put faith in the front office’s insistence that it would surround him with championship-caliber players. That he’d stick around and deliver a ring to the glory-starved Cavs. 

Instead, LeBron joined Dwyane Wade—and, later, Chris Bosh—in Miami to form a superteam that would finally achieve glory in 2012, leaving the Cavs with nothing. To add insult to injury, he announced his decision in an infamous, PR-disaster-of-a-TV-special on ESPN, which has often been described as the equivalent of dumping a girl on national television. Cleveland, of course, is the girl. 

For seven years, Cleveland dedicated itself to its lone superstar. To this day, Cavs fans can barely see a photo of LeBron without descending into a rage blackout.