These Sports Icons Should Have Quit When They Had The Chance

Darren - December 1, 2023

These Sports Icons Should Have Quit When They Had The Chance

Darren - December 1, 2023

Every sports team has legends and icons that fans idolize. They range from all-star players who gave everything for the team and dazzled with their performances to elite coaches with brilliant minds who masterminded victory. But sometimes, these sports icons stay too long and it becomes obvious they should have quit earlier.

So today we’ll look at top players and coaches who didn’t know when to stop. Maybe their sport simply passed them by or the environment changed around them. But the results didn’t go their way and they endured humiliating ends to otherwise great careers. Remember the sports icons who stayed past their welcomes right here.

Sporting News

Ben Roethlisberger

‘Big Ben’ was one of the Steeler’s most iconic quarterbacks of all time but still should have quit earlier. The quarterback became a legend when he helped them to two instances of Super Bowl glory. This ensured his place with the team for the next decade or more. It’s easy to question his personal life and sordid antics outside football but there’s no denying he was a great player.


However, injuries caught up with him and took their toll on his body toward the end of his career. He missed most of the 2019 season with an elbow problem and was never the same after. It also delayed the Steelers’ ability to plan his succession because they still had their highly-paid franchise superstar on their roster (via CBS Sports).


Aaron Rodgers

Rodgers is one of the two greatest quarterbacks of his era. His diehard fans constantly point out that statistically, he’s better on the field than Tom Brady. He doesn’t have the records or the same number of rings but he’s still an iconic player. However, he made a mistake when he joined the New York Jets in 2023.


Yes, Rodgers saw the chance of a new challenge and believed he’d instantly transform them into contenders. Nobody could have predicted his Achilles injury but it was a risk that he didn’t need to take. He should have quit early and taken a cushy broadcasting contract. But that’s also a reason why the Super Bowl champion is a true competitor (via SNY).


B.J. Penn

‘The Prodigy’ was one of the most exciting MMA fighters ever. Penn emerged from Hawaii with a vengeance and became a two-weight UFC champion while also fighting in K-1 and Brazilian Jiu-Jitsu. He had a very exciting style and provided the UFC with some iconic moments and matchups.

Phoenix New Times

But he should have retired earlier because things fell apart. Father Time doesn’t wait for anybody and Penn fell into a rapid decline. He failed to win his final eight UFC fights with some atrocious performances. The promotion also received criticism for continuing to book him because he wasn’t the same (via MMA Junkie).


Brett Favre

There’s sometimes a revisionist narrative that Favre was never that good, which is ultimately ridiculous. He was a brilliant quarterback in his prime and there’s a good reason why the Packers kept him for so long. However, it’s also true that he should have quit earlier. If he walked away from Green Bay with his head held high, his legacy would be completely different.

Acme Packing Company

But then there was that sexual harassment scandal in New York while his numbers suffered a stark decline. He also played for the Vikings for no good reason and didn’t offer much on the field. It’s a shame that we can’t separate the end of his career from his excellence for the Packers (via Sports Illustrated).


Ed Reed

Analysts were saying that Reed should have retired before he left Baltimore. So it’s not shocking that the voices became louder when he played for the Texans and the Jets. 2013 was a garbage year for the legendary safety because he fluttered between two franchises before hanging up his cleats.

San Diego Union-Tribune

Remember, Reed was outstanding for the Ravens during his prime as he helped them achieve Super Bowl glory. Reed also won the NFL Defensive Player of the Year award in 2004 and regularly led the league in interceptions. Unfortunately, his love of football kept him on the field a little too long (via Bleacher Report).

Sports Illustrated

Patrick Ewing

Ewing is a Knicks icon and should have won an NBA Championship with them. However, he never got his hands on a coveted ring. Nonetheless, he went down as one of the greatest basketball players of all time. But it’s better to forget about his final days in the NBA because they didn’t add much to his legacy.

Arguably, he should have retired earlier because the Hall of Famer joined the Sonics before a stint in Orlando. Neither of these went well because he was past his prime. Luckily, this didn’t damage his legacy much but it was a disappointment to fans of those franchises (via Fansided).


Jerry Rice

Many people think that Rice was the greatest wideout and arguably even the greatest player in NFL history. That’s an incredible statement because there have been so many top athletes in the league. But Rice was at another level and helped the Niners to three Super Bowls over 15 seasons. The two-time Offensive Player of the Year was outstanding but should have retired earlier.

Pro Sports Outlook

Rice could have walked away at the end of his tenure with the 49ers but couldn’t bear to hang up his cleats. He had a few solid seasons with the Raiders before he bounced to the Seahawks and the Broncos. But he wasn’t the same player with those last two teams and it was a shame to watch his ghost trying to reclaim past glories (via Boardroom).


Mike Ditka

Ditka became an NFL legend when he played his part in the Bears winning Super Bowl XX in 1985. This aged well because Chicago has been dreadful over the past couple of decades so it means even more to the franchise. The Bears smashed the Patriots and Ditka became a Chicago icon.


However, he arguably should have walked away from football with his head held high. Instead, he took another job with the New Orleans Saints but it was an unmitigated disaster. They took a decade to recover from the Ricky Williams Draft fiasco because he traded all of their picks away (via ABC News).


Sir Alex Ferguson

‘Fergie’ is the most successful soccer coach in English history. The Scottish manager led Manchester United for over two decades to unprecedented glory. He had complete control over the team’s fortunes but this was arguably a disaster for the team. Some critics think that he knew that he left the team in a weak position when he quit in 2013.


United won 13 Premier League titles with Ferguson in charge but haven’t won another since. Many analysts believe that their directors should have had a better succession plan in place for when he left. The quality of coaching, recruitment, and even the stadium declined when he departed (via ESPN).

Sports Illustrated

Philip Rivers

Some people might laugh at calling Rivers an ‘icon’ but he is a Chargers legend. This is the man who played a full game with a torn ACL and thought nothing of it. He was one of the best quarterbacks in an era of legends. However, he should have quit instead of joining the Colts on a short-term deal.


He was already suffering a downturn and many Chargers fans didn’t mourn his departure. That’s a shame because he gave them over a decade and a half of service. But there’s no sentiment in professional sports because it’s all about winning now. In the end, Rivers wasn’t that man anymore (via Sports Illustrated).


Steve Nash

Many NBA fans agree that Nash is one of the greatest players without a ring. He had a brilliant career with his best performances coming for the Suns and the Mavericks. It’s easy to forget that he had a short but ultimately unsuccessful spell with the Lakers (via Basketball Network).

Bleacher Report

Nash was 40 when he finally retired and deserves credit for his longevity. But the fact is that his last three seasons were garbage. Nash admitted that it disappointed him that he wasn’t able to take to the court as he wanted. Father Time is a cruel master as he discovered.

CBS Sports

Emmitt Smith

Sometimes a player is so amazing that it seems impossible they could fail. Smith was one of the best running backs in NFL history and set countless records with the Dallas Cowboys. He even won the 1993 MVP Award during an era when that was still possible. A three-time Super Bowl champion, there’s no other way to describe his time in Dallas than simply outstanding.


That’s why his time in Arizona makes no sense. Everything went wrong for him and he should have quit before joining them. Smith suffered injuries and a serious dip in production. He was too old and the new scheme didn’t fit him. However, nobody remembers that anymore (via Sports Illustrated).


Michael Schumacher

Every Formula 1 fan knows Schumacher because he was one of the most dominant champions ever. The German won seven titles as Ferrari led the way in style. However, he loved racing too much and carried on longer than he should have. Schumacher couldn’t stay away from the sport because he loved the attention and buzz.


He quit first in 2006 before he returned four years later to race for Mercedes. However, Schumacher had a negligible impact on their team before they replaced him with a young Lewis Hamilton. He didn’t put the same fear into his opponents on the track because he wasn’t the same driver (via The Mirror).


Cristiano Ronaldo

Ronaldo is one of the most iconic players of his generation. The multi-time Ballon d’Or winner had an incredible rivalry with Lionel Messi and won countless titles. He won trophies with Manchester United, Real Madrid, and Juventus. However, it’s fair to say that he handled the end of his career badly.

Sky Sports

The Portuguese star opted to return to United but was garbage and his coach cast him off. Ronaldo then joined Saudi Arabia’s Al Nasser because he decided he didn’t have enough money. This didn’t go down well amongst many supporters who felt that he tarnished his legacy (via GOAL).


Allen Iverson

Iverson was one of the NBA’s top players during his time in Philadelphia. He set electrifyingly high standards as he averaged 20 points per game. That’s also why he became a fan-favorite amongst a diehard base. However, Iverson didn’t know when to quit and became an NBA nomad (via Fox Sports).


It’s very typical for players to jump around franchises at the end of their careers. They’re desperate to secure that final big contract before they inevitably retire. However, it’s sad to see them as shadows of their former selves. Iverson also played for the Pistons, the Nuggets, and Memphis to little impact before he finally stepped away.


Michael Jordan

Why did Jordan come back and play for the Washington Wizards? This remains a question that stirs up debate amongst NBA fans and analysts today. He returned from retirement to play for the franchise after an incredible era with the Bulls. Jordan put up average numbers in the capital because he was old and no longer the same force.

Sports Illustrated

Nonetheless, every team wanted him for marketing reasons before he opted to play in Washington. He had a minority share in the franchise but the rules forced him to sell them before playing. Meanwhile, they only paid him one million dollars per year and that was peanuts to him (via Sportskeeda).


Conor McGregor

McGregor is a strange case because he’s one of the most lucrative athletes in the world. However, the reality is that he may be a billionaire so why does he want people to punch him in the head? He made his fortune by tricking the world into thinking he could beat Floyd Mayweather as well as selling whiskey.

Fox News

However, his MMA record since then isn’t great with multiple losses. Khabib Nurmagamedov and Dustin Poirier both inflicted chastening defeats on the Irishman. Perhaps his wealth and fight knowledge would better serve him if he walked away. McGregor is clearly focused on business instead of fighting, so there’s no reason to act like he’s going to fight anytime soon (via Sportskeeda).

Bleacher Report

Mack Brown

Brown won a national title with the Longhorns as he revived their program. People started taking Texas seriously again because of this great head coach. He made Vince Young and Colt McCoy into two of college football’s best quarterbacks. But then everything went wrong and he should have quit earlier when the fans loved him.


The Longhorns had recruitment problems and struggled to replace McCoy after he turned pro. They struggled for a few seasons before Brown finally departed. It was a shame because it dented his reputation but a break was good for him. Now he’s in his second spell with UNC and is arguably their greatest coach ever (via Texas Monthly).


Evander Holyfield

Holyfield is a boxing legend with multiple boxing titles under his belt. He had epic rivalries and matches with Mike Tyson and Riddick Bowe. He also fought for a very long time and didn’t quit until he was almost 50. This concerned many people who didn’t understand why he kept putting his health at risk.

Sky Sports

It also meant that he wasn’t the same athlete and he should have walked away earlier. However, Holyfield had many debts and also loved the bright lights too much. We’ve seen this story with many athletes over the years and he was no exception. Hopefully, he doesn’t pay a heavy price in the future (via Boxing Social).


Tom Brady

Brady had the perfect opportunity to walk away with his head held high. He won a miraculous seventh Super Bowl when he joined the Tampa Bay Buccaneers in a glorious achievement. However, he should have quit earlier because the following season didn’t go well (via Forbes).

CBS Sports

Age finally caught up with the legendary quarterback because his play deteriorated. This left him open to criticism and it also put the Bucs in an awkward position because he didn’t commit to retirement. In the end, he played one season too many because he had the chance for a fairytale ending.


Arsene Wenger

Wenger is another legend of English soccer. The Frenchman revolutionized the league when he joined Arsenal in 1996. He changed his players’ diets and brought sports science to new levels. Meanwhile, he won multiple titles including the Premier League during the iconic ‘Invincibles season.


But the problem was that he should have quit earlier. Wenger departed in 2018 but he became a caricature of himself. The team struggled to compete with the Manchester Giants and Chelsea. Then the fans turned on him and his departure became inevitable. It’s sad because he should have left on his terms (via Sky Sports).


Shaquille O’Neal

Shaq was arguably the league’s top player when he was in his prime with the Lakers. The four-time champion won the MVP award in 2000 and his career spanned almost two decades. But arguably he should have retired earlier because he faded with a whimper. O’Neal played for the Celtics and the Cavaliers after he left L.A.


However, injuries and fitness issues reduced his ability to play games. The latter problem came from a lack of motivation as he aged and edged closer to retirement. It’s a shame he didn’t quit after he left the Lakers because it would have been special. The reality is that we rarely see these fairytale endings (via Bleacher Report).

Fox Sports

Chuck Liddell

Liddell was one of the UFC’s first mainstream stars. The MMA icon became a fan favorite because of his mohawk and devastating fighting style. He was a berserker in the cage as he became the UFC light-heavyweight title. But Father Time caught up with him and he finished his MMA career with only one win in his last seven matches.

NBC Sports

Even worse was the fact that he suffered five knockouts during that run. Liddell couldn’t resist the allure of the bright lights despite the UFC giving him a cushy job. Dana White looked after his friend and tried to stop him fighting when he was almost 50 in 2018. It was sad to see him lose again (via USA Today Sports).


Muhammad Ali

Many people still think that Ali is the greatest heavyweight champion ever. Nobody had seen anything like him before because he had devastating movement and dynamism in the ring. However, he changed his style completely after the Vietnam War and he began to take more damage. He should have quit earlier but he didn’t.


Losses against Larry Holmes and Trevor Berbick inflicted more long-term suffering on the icon. Later he endured Parkinson’s Disease and struggled with it for the rest of his life. It was sad to see him struggle so much after being a towering emblem of masculinity (via USA Today).

Bill Belichick

Belichick is one of the most legendary head coaches ever with an incredible six Super Bowl rings. He led the Patriots to unprecedented glory but there’s a strong argument that he overstayed his welcome. Some people think that he continued because he wanted to prove that he could win without Tom Brady.

AP News

However, he risked tarnishing his impressive legacy and suffering the indignity of being fired. Belichick started the 2023 season with a dismal 2-9 record on his way to a second successive losing year. He should have quit when he had the chance because there was nothing left for him to prove (via Forbes).