11 Athletes Who Could Have Gone Out On Top - But Didn't



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Voting Rules

Vote up the sports stars who should have left on a high note.

The old cliche “go while they still want you to stay” is worthy advice for almost anyone - from movie stars who want to be remembered for the roles and beauty at their pinnacles, to house guests who want to ensure they'll receive another invitation in the future.

It's also relevant to professional athletes, who devote years - sometimes even decades - to reaching the height of their careers. Many are then content to retire from their chosen sports on a high note. However, some push themselves to keep competing even when they're past their prime, whether via a continuous run, or after an ambiguous period of retirement.

Check out the following list, and vote on which athletes should have left well enough alone, but instead ended up leaving with their tails between their legs.

Photo: El Gráfico / Unknown author / Wikimedia Commons / Public domain

  • The outcomes may be predetermined, and an experienced performer can mask his declining skills for a long time, but even pro wrestlers have to call it quits someday. Father Time is no easier on sports entertainers than on legitimate athletes. Few pro wrestlers have embodied this struggle quite like the “Nature Boy” Ric Flair.

    He was once one of pro wrestling’s biggest draws, but the ravages of such a hard-knock profession and playboy lifestyle were sorely apparent in Flair’s in-ring work as far back as the late 1990s. He continued to wrestle well into his 50s with WWE and entered into a storyline in 2008 where if he lost, he would retire for good. 

    After a string of unlikely wins, Flair finally came unstuck at WrestleMania 24 in a match with Shawn Michaels. 

    When Michaels pinned him, there wasn’t a dry eye in the house as the 59-year-old rose slowly to his feet and walked out of the arena to rapturous applause - the perfect end to a long career.

    Or it should have been. Flair signed with a rival company and returned to the ring in 2009, wrestling sporadically in low-quality matches, a time he later looked upon with regret. Financial troubles stemming from failed investments and the lure of the spotlight kept him coming back for more for years. His most recent “last match” took place in 2022 at 73, where he passed out twice during the match.

  • Muhammad Ali - Too Tough For His Own Good
    Photo: Frictional / Wikimedia Commons / CC BY-SA 4.0

    The greatest heavyweight boxer of all time, Muhammad Ali (born Cassius Marcellus Clay Jr.) just couldn’t walk away when the time was right. He first contemplated retirement in the wake of the rubber match with Joe Frazier, known as the “Thrilla in Manila” way back in 1975. Neither fighter was ever the same after that titanic battle.

    However, Ali’s name was such a huge draw that the temptation to have just one more fight was too great to leave well enough alone. Tough victories over Ken Norton and Ernie Shavers offered yet more opportunities to walk away with his legacy and health intact, but those closest to him wanted to wring a few more dollars out of their golden calf. 

    Ali's personal physician, Ferdie Pacheco, urged him to call it quits after the hard-fought win over the notoriously hard-hitting Shavers and resigned when Ali elected to keep going. Pacheco outlined the conundrum he faced back then:

    How can you keep a guy from making $8 million in the ring because of something in your head that tells you he's shot? He may take a beating when he doesn't have to, but how do you prove that on a meter?

    After a shock loss to relative newcomer Leon Spinks in 1978, Ali just had to regain the title, which he did to become a three-time world champion. What was left to prove after that? 

    Larry Holmes put a definitive end to Ali’s career as a top-level boxer in 1980. Holmes, who would have been a threat to even a prime Ali, simply trounced the aging champion. He even pulled some of his punches, not wanting to seriously hurt his illustrious opponent. After the 10th round, Ali’s trainer Angelo Dundee called a stop to the fight - Ali’s first and only stoppage.

    Once again, that really should have been it, but the manner of the defeat wasn’t something such a proud fighter could bear. Desperate to go out with a win, the now 39-year-old Ali took a match in the Bahamas with Canadian boxer Trevor Berbick - the “Drama in the Bahamas” was the moniker given to his final fight.

    Dundee was firmly against Ali taking the bout, but agreed to be in his corner to protect Ali from himself if he got into trouble. Berbick almost pulled out due to pay issues, while the arena struggled to sell tickets, slashing the prices from $50 to just $5. In the end, Ali was defeated comfortably via decision and finally decided to call it a day:

    I know myself better than anybody else, and I know it's the end. It's not that the magic may be gone, it is gone.

    The Parkinson's disease symptoms Ali suffered later in life may have been caused by the longevity of his career. For all his skill in avoiding punches, he was perhaps a little too good at taking them as well.

    • Age: Dec. at 74 (1942-2016)
    • Birthplace: Louisville, Kentucky, USA
    160 votes
  • Tom Brady called time on his football career following the 2021 season. The “retirement” lasted less than six weeks before he chose to play on for one more season with the Tampa Bay Buccaneers. His swan song campaign was marked by indifferent form and off-field troubles that did little to bolster his legacy as one of the sport’s all-time greats.

    He already had the perfect time to bow out - right after Super Bowl LV. After clinching his seventh Super Bowl in 2020, he could have walked away a champion at 43. He still put up a pretty good showing the following year, but time finally caught up with Brady in 2022 and ended his illustrious career with a whimper. Nobody could blame him for wanting to go for as long as he could; most of us would do the same. But after such a difficult year professionally and personally, was it really worth it?

  • Chuck Liddell - From Granite Chin To Glass Jaw
    Photo: Bad intentionz / Wikimedia Commons / CC BY 3.0

    Chuck “The Iceman” Liddell is a bona fide legend of mixed martial arts. With a gutsy all-action style and an ability to stuff takedowns to keep fights standing, he was a firm favorite with fans. With a chin seemingly carved from granite, he’d walk opponents down and take whatever they had before unleashing his own barrage of punches.

    He reigned supreme in the light-heavyweight division in the mid-2000s before he was stopped by Quinton “Rampage” Jackson in his fifth title defense, and later brutally finished by Rashad Evans. He was never quite the same after that. 

    After three losses in a row by knockout, it was clear his ability to take a punch had vanished, and he was finally talked into retirement in 2010 at the age of 41. He was offered a “lifetime” job with the Ultimate Fighting Championship, and with hopes of an acting career, he seemed set for a comfortable life after fighting.

    It didn’t last. A takeover of the UFC saw Liddell axed from his sinecure position, and with a lifestyle well beyond his means, he was lured back into the octagon to fight arch-rival Tito Ortiz. He’d already beaten Ortiz twice in 2004 and 2006 back when both were top names in the sport. By 2018 neither had anything like that kind of star power. Despite some worrying training footage, the fight went ahead and Ortiz easily vanquished Liddell in just 30 seconds.

    • Age: 53
    • Birthplace: Santa Barbara, California, United States of America
    91 votes
  • Björn Borg - Quit Tennis At His Height, And Couldn't Climb Back A Decade Later
    Photo: Rob Bogaerts / Anefo / Wikimedia Commons / Public domain

    Björn Borg, a native of Sweden, conquered the tennis world in the late 1970s and early '80s, winning Wimbledon five times in a row and six French Open titles. He was known for his composed demeanor on the court - a cool counterpart to his fiery American rival John McEnroe. 

    However, just as suddenly as Borg rose to the top, he quit tennis altogether when he was just 26 - not even in a pro’s prime years. It turned out that beneath that icy exterior, the pressure of top-level tennis and the demands of training were taking their toll on his mind and body. He walked away from it all in 1983, seemingly for good. That was, until a 35-year-old Borg decided to make a comeback in 1991.

    Cynics suggested his tennis reprise was doomed to failure, that the sport had moved on in his absence and he wouldn’t be able to compete against modern players. They were right.

    Borg appeared in several tournaments from 1991 to 1993 without any success whatsoever.

    • Age: 66
    • Birthplace: Stockholm, Sweden
    74 votes
  • Babe Ruth - Couldn't Move But Could Still Hit
    Photo: Irwin, La Broad, & Pudlin / Wikimedia Commons / Public domain

    The name of George Herman "Babe" Ruth Jr. became so synonymous with sporting excellence that stars of other sports were sometimes called “the Babe Ruth” of their respective sports. Such was his stardom that after his controversial trade from the Boston Red Sox to the New York Yankees in 1919, the Red Sox endured an 85-year drought for another World Series, while the Yankees won four in the next decade after signing Ruth. 

    Toward the end of a glorious career, Ruth wanted to get into management, but his many off-field exploits weren’t appealing to club owners. He accepted an offer in 1935 to return to Boston as a player, albeit for the Boston Braves (now in Atlanta).

    By this point of his career, Ruth's lifestyle had caught up with him, and he was signed more for his drawing power than his playing ability. He could still hit, but could scarcely make it around the bases and was a defensive liability. 

    Ruth only played 28 games, but rolled back the years to hit his final three home runs in 1935 to bring the curtain down on a remarkable career. As dismal as his final season was by his own high standards, it did little to diminish his legacy as one of baseball’s greatest-ever players.

    • Age: Dec. at 53 (1895-1948)
    • Birthplace: Pigtown, Baltimore, Maryland, United States of America
    94 votes