Garciaparra was a top MLB player and the Red Sox knew it. They offered him a massive four-year extension worth $60 million. But then they tried to trade him for the Rangers’ Alex Rodriguez. This infuriated Garciaparra and he rejected the new contract. Perhaps he should have swallowed his pride and put pen to paper.
Business isn’t personal and Garciaparra didn’t accept this. In the end, it cost him dearly as he signed up for one year with the Cubs. But they only paid him eight million dollars while he would have earned almost twice that per year if he signed with Boston (via BroBible).
The ‘double doink’ remains one of the most infamous NFL field goal attempts ever. Parkey watched his life flash before his eyes after his kick. Somehow, he hit the bar for the sixth time that season. Meanwhile, the ball bounced off the upright onto the crossbar in an agonizing fashion.
Parkey had a chance to be a hero had a successful kick won the Bears the game. This would have sent Chicago to the divisional round but that’s not what happened. Instead, Parkey experienced a career-defining moment because fans will only associate him with this notorious miss for the rest of his life (via The Guardian).
Kahn had a brilliant 2002 World Cup as he helped Germany reach the finals. There, they played Brazil but suffered a devastating loss. Unfortunately, Khan committed a career-defining error as he undid his good work. He allowed a tame shot to bounce off his gloves into the path of Ronaldo.
The prolific Brazilian took advantage and scored the crucial goal to win the game. It was a brutal moment for Kahn because he had an excellent tournament until that moment. In the end, his team paid the price as they watched the Brazilians lift the trophy high (via Bundesliga.com).
Bell was excellent during his time with the Pittsburgh Steelers but he destroyed his career. He emerged as one of the NFL’s most exciting players but he grossly overestimated his value. He sat out for a full season in his prime because he thought he could make more money elseshwere. This was a career-defining mistake as Pittsburgh shrugged their shoulders.
Then he paid for his mistake because he went to the Jets. Their neew head coach Adam Gase was a disaster and failed to get the best out of Bell. After a couple of seasons, Bell managed to wrangle a move to the Kansas City Chiefs. But he failed to make much of an impact for the Super Bowl contenders (via SBNation).
Aspas is a Celta Vigo legend but the Spanish forward had a nightmare of a time in Liverpool. Brendan Rodgers brought him to Merseyside because he wanted to spice up his front line. However, Aspas barely made an impact before his inevitable return to his native country (via The Hindu).
Furthermore, one moment summed up his entire Liverpool career. Aspas took a corner against Chelsea when his team was behind. They required a good ball into the box to try and test the goalkeeper. But he passed it directly to Chelsea’s Willian, who instantly broke downfield in a humiliating moment.
Ewing was a brilliant player and remains a Knicks icon. However, he ultimately personifies the most frustrating aspects of the franchise. Ewing took the team within touching distance of glory but fell short at crucial moments. One notorious and career-defining moment came in the playoffs against the Miami Heat.
The series went all the way to Game Seven and Ewing had an opportunity to win. The ball came his way and it appeared that he would dunk it. But the clutch situation affected him and the ball rolled away from him instead. This proved costly and ultimately became a career-defining moment (via N.Y. Post).
Kish will always be the UFC fighter who pooped her pants in the ring. It’s unfortunate but that’s her athletic legacy in a nutshell because nobody remembers anything else about her. She fought Felice Herrig in a UFC event when her body betrayed her in the most unfortunate way (via Men’s Health).
Herrig had Kish in a compromising position and was choking the life out of her. This triggered the Valsalva maneuver that causes the diaphragm to work. It also places stress on the lower parts of the body as Kish discovered. In the end, she left a mess that no one wanted to see.
Sentiment and professional sports go together like water and sodium. Unfortunately, nobody told John McNamara because he cost the Red Sox a World Series. McNamara consistently brought the veteran Buckner into games throughout their playoff run as a late replacement (via SBNation).
Then he decided to keep Buckner in the final match of the World Series. He thought the Red Sox had an insurmountable lead. But Buckner made a career-defining error as he allowed a ball to bounce between his legs. Many Boston fans resented him but it was McNamara’s fault for putting him in the position.
Bergevin made one of the strangest career-defining mistakes in hockey history in 2000. He played for the St. Louis Blues against the San Jose Sharks when he committed the embarrassing error. Bizarrely he accidentally tossed the puck into his team’s net and scored at the wrong end.
It took a few moments for everybody to register what had just happened. The moment felt inexplicable because it appeared that he tossed it into the goal. This wasn’t intentional but the moment sticks in the memory of everybody who watched it. Nobody will forget Bergevin’s most infamous incident (via Sports Net).
The Ricky Williams trade remains one of the most confusing moments in NFL history. New Orleans hired a Super Bowl winner in their new head coach Mike Ditka as they tried to bring their franchise to the next level. However, this decision ultimately set the team back many years.
Ditka decided to trade every draft pick the team had in exchange for Williams, a running back. It’s unthinkable today because nobody even selects running backs in the first round. In the end, Williams had an average career but didn’t justify the Saints’ massive sacrifice for him (via Bleacher Report).
English goalkeepers have a long history of committing terrible career-defining mistakes. Green added his name to this unwanted list during the 2010 World Cup. England played the United States in a group game. Clint Dempsey took an optimistic shot that skidded across the ground and bounced off Green’s palms.
Green dropped the ball and it trickled agonizingly into the net. It was a nightmarish moment for the West Ham star because it cost his team a win. England dropped him in favor of David James in the next match. He barely played for his country again after this horrible moment (via The Guardian).
It’s safe to say that Jones isn’t the second coming of Eli Manning. He replaced the legendary Giants quarterback but failed to inspire the team’s offense. That’s why the franchise declined to take up his fifth-year option because they didn’t think he is worth the investment.
One moment summed up his entire career in New York. He went on a remarkable 80-yard run against the Eagles after he found himself in open space. It appeared that a brilliant touchdown was inevitable but then he tripped over himself. This was a perfect metaphor for Jones and the NFC East (via CBS Sports).
Elite athletes must remain professional and focused throughout their competition. If they relax for a single moment it could produce a career-defining event. Jacobellis discovered this most heartbreakingly when she threw away her chance of a gold medal in 2006.
She had a phenomenal record in the X Games but failed to win first place in the Winter Olympics. Jacobellis built up a massive lad during her final race but then she decided to showboat. This was a fatal decision because she lost her balance and suffered an ill-timed fall (via USA Today Sports).
Yashin was a top NHL player but his team infuriated him. We’re talking about the Ottawa Senators who failed to offer him the terms that he wanted. This caused him to sit out for a season in a career-defining decision. In the end, the Senators sued him because they claimed that he failed to fulfill the terms of his contract.
A court of arbitration agreed and forced him to play for one more season in Canada. Finally, he escaped and moved to the New York Islanders. But it was a nasty contract dispute and one of the most notorious in the history of professional sports. This shadow hung over Yashin for a long time (via The Hockey News).
Coutinho became one of the most exciting players in the world during his time with Liverpool. However, everything when Barcelona displayed an interest in the Brazilian midfielder. He dreamed of moving to Spain and playing with his national teammate, Neymar. Coutinho put pressure on the Reds in a bid to force a sale.
In the end, he received his wish but it didn’t work out well for him. On paper, he won many trophies but it tarnished his legacy. Coutinho became a fringe player and went on loan to Bayern Munich. Meanwhile, Liverpool reinvested their earnings in the team and took a giant step forward (via The Athletic).
Stefan saw his name in light before one of the worst misses in NHL history. The Dallas Stars forward had a chance to seal the win for Dallas against the Edmonton Oilers. The net lay open in front of him and it appeared impossible that he could miss. But that’s exactly what happened with devastating consequences for the Stars.
Instead of securing the game for Dallas, Stefan threw away the win. Edmonton immediately responded to the miss by scoring an equalizer and sealing a tie. However, this career-defining mistake affected the future of the franchise. They failed to draft Patrick Kane because of Stefan’s miss (via Dal Sports Nation).
Carson is another English goalkeeper who made a career-defining error on the world stage. He had a big reputation when he played against Croatia and hoped to seal his place as England’s starter. One of the Croatian players took a long-range shot that bounced in front of the keeper.
He fumbled the ball and it embarrassingly rolled into the net. Instantly, the media vilified Carson and it effectively killed his international career. It took a long time for him to rebound from this moment because people constantly brought it up (via The Guardian).
Joshua was one of the most marketable heavyweight boxers on the planet. However, he made a terrible error when he agreed to fight Andy Ruiz on short notice. Ruiz replaced Jarrell Miller after the latter failed a drug test. Nobody gave the heavyset Mexican fighter a chance because of his rotund physique.
Later it emerged that Joshua suffered a recent knockout in training. Perhaps this affected his performance because he failed to overwhelm his opponent. He knocked Ruiz down early but the Mexican came storming back. Then Ruiz secured the finish after Joshua failed to answer the referee’s count in the seventh round (via Insider).
Zidane was brilliant in the 2006 World Cup as he led France to the finals. They played Italy in the showpiece event and depended on their captain. He scored an early penalty as they took the league but he cost his team the game. This came after he hit Marco Materazzi with a brutal headbutt.
Materazzi allegedly insulted Zidane’s sister and mother but the Frenchman’s reaction was disproportionate. He responded to the bait with violence and potentially cost his team the win. It became an iconic and career-defining moment because of the drama (via NZ Herald).
People don’t remember much about Piscarcik’s career except for the ‘Miracle at the Meadowlands.’ This saw one of the worst play calls in NFL history but it wasn’t his fault. He had problems with offensive coordinator Bob Gibson and made his feelings known throughout the season (via CBS News).
Everybody thought Pisarcik would take a knee against the Eagles with a win in sight. But Gibson ordered him to pass to Larry Csonka. The quarterback opted not to rock the boat and followed this instruction. However, he fumbled the pass and the Eagles seized the ball for the game-winning touchdown.
There’s a time and a place to take a break during a game of soccer. Unfortunately, Brazil’s Roberto Carlos decided to tie his shoelace at the worst possible moment. He didn’t wait until the ball went out of play. France received a free kick in a dangerous position and Carlos left Thierry Henry unmarked.
The brilliant French striker raced behind the Brazilian defense and scored the winner. It was a horrible moment for Carlos because it was completely his fault. He didn’t do anything to put Henry off and the French striker took full advantage. This was a very disappointing tournament for the Brazilians (via The Sportsman).
Nobody expected Bradbury to win a gold medal in Salt Lake City in 2002. But that’s exactly what happened for the Australian in one of the few positive stories on this list. He made the final of the short-track speed skating race as an outsider. However, soon, everybody would know his name after a career-defining performance.
It was like the tortoise racing against the hare because he fell behind the pack. Nonetheless, he benefited from this because the other athletes crashed and had a massive pile-up. Bradbury skated past them and maintained his composure on his way to a historic victory (via Olympics.com).
Many goalkeepers are a little crazy, but Higuita took this to the next level. Fans remember his stunning scorpion kick save against England because it was a ludicrous moment. But sometimes his madness cost Colombia dearly because it was too much. The team reached the quarterfinal against Cameroon but Higuita sent his nation home.
He dribbled the ball out of his area into a dangerous area. Suddenly, Cameroon’s legendary striker, Roger Milla intercepted him and stole the ball. He calmly slotted it home and Colombia packed their bags. Higuita admitted that it was a massive error but he remains a cult hero (via ESPN).
Askren built up a strong reputation during his time as champion with ONE Championship in Singapore. The American fighter had a strong wrestling base and he used this to dominate his opponents. He joined the UFC as a veteran with mixed results. But he talked his way into a clash with Jorge Masvidal that proved to be career-defining.
At the start of the bout, he moved forward with his head down as he attempted to shoot for a takedown. However, Masvidal predicted this move and instantly came forward with a brutal flying knee. It was the fastest knockout in UFC history and Askren’s career never truly recovered from the moment (via TalkSport).
Many people on this list paid a hefty price for their career-defining mistakes. But nobody suffered a cost as high as Escobar after he scored an own goal against the U.S. in the World Cup. It was an unfortunate moment and a low point for the Colombian international.
Then he went home after the tournament to visit his family. But a gunman confronted him outside a bar and murdered him in a brutal fashion. Allegedly he referred to Escobar’s mistake and slayed him for it. Escobar had no relation to the infamous drug lord of the same name (via The Sun).
Usman was on course to eclipse Georges St-Pierre as the greatest UFC welterweight champion of all time. He fought the UK’s Leon Edwards in a title fight in Salt Lake City. Edwards had a good first round but Usman settled and dominated his rival. People began to leave early into the fifth round because the fight appeared to have run its course.
Then, out of nowhere, Edwards smashed Usman in the head with a brutal kick. It was perfect timing because he waited for Usman to drop to one side without keeping his guard up. This career-defining mistake changed Usman’s legacy and meant that he’d never be the greatest of all time (via MMA Fighting).
The Pistons faced the Celtics in the Eastern Conference Finals in 1987. Boston trailed by a single score with 10 seconds left on the clock. It appeared as though their luck had run out and that Detroit would claim a historic victory. But then Thomas made a career-defining error that cost his team the series (via USA Today Sports).
Larry Bird snatched an inbound pass from Thomas who should have tried to run down the clock. All he had to do was run down the clock but he failed miserably. Then Bird passed to Dennis Allen who sealed the victory for his franchise. The Pistons lost against the Lakers in the Finals but this was a day of ecstatic celebration.
Nedved is another example of a player who overestimated his value. The Penguins offered him about $17 million for a one-year extension in 1997. However, Nedved held out for $20 million in one of the dumbest bargaining moves ever. Pittsburgh shrugged and refused to play ball.
If Nedved expected other NHL teams to come to the table he was mistaken. He sat out for the year and didn’t make a dime in salary because of his greed. Players should know their worth but sometimes pragmatism is important. In the end, it was a costly mistake for Nedved (via Olympics.com).
Technically this isn’t a mistake because Smith knew what he was doing. However, he didn’t intend for people to know that he carried a prosthetic urination device in his bag. The Whizzinator entered NFL folklore after he passed through an airport with dried urine and a mysterious appliance.
The NFL discovered that he was attempting to cheat the system. This had career-defining consequences because Smith was a known drug cheat. He served a one-year suspension but then he became damaged goods. Nobody wanted to sign the running back after his shenanigans (via CBC).
Suarez was one of the most talented players in world soccer during his heyday. However, the Uruguayan consistently lived on the edge and resorted to the dark arts. There’s no denying that he intentionally committed a handball against Ghana in the World Cup. But other heinous actions were heinous mistakes.
One of his most career-defining habits was biting opponents. He infamously chewed on Italy’s Giorgio Chiellini as well as Chelsea defender Branislav Ivanovic. It’s bizarre that this was his automatic reaction to adversity but it tarnished his reputation. He received psychological counseling after the final biting incident (via Insider).
Combat sports athletes learn the mantra “defend yourself at all times.” However, a former Glory kickboxing champion forgot these words when he fought Murthel Groenhart. He turned his back against the Dutch fighter while the fight was still on. Groenhart instantly exploited Grigorian’s error and knocked him unconscious.
It was a confusing moment but Groenhart didn’t do anything wrong. He punched a legal target and the referee hadn’t stopped the fight. But Grigorian’s team and fans reacted furiously as they stormed the ring. They also attacked Groenhart in scandalous scenes (via Glory Kickboxing).
During her prime, Harding was America’s darling. The figure skater came from a working-class background but she didn’t allow this to hold her back. She broke multiple records but then she made a terrible mistake. It came after her ex-husband attempted to break Nancy Kerrigan’s leg.
Harding attempted to pretend that she didn’t know anything about this and she received a lot of legal consequences. It was a career-defining moment because she never shook the stain off. This was a massive shame because she had so much talent but she ruined everything for herself (via Biography.com).
Marshall was a brilliant defensive end for the Browns and the Vikings. However, he dropped one of the biggest clangers in NFL history. Imagine recovering a fumble and returning it for a touchdown. Nothing seems wrong with this sentence on the face of it but Marshall made a key error (via History.com).
Somehow the defensive end contrived to run the wrong way up the field back to his team’s end zone. He charged unopposed for 66 yards in the wrong direction. Nobody could believe what they were watching because it was so ludicrous. In the end, Minnesota still won the game but this was a career-defining memory.
Everybody remembers when Michael Jordan scorched Russell and left the Bulls with a final ring. It was the last appearance of Jordan’s professional basketball career and sealed his legacy. But it was also a career-defining moment for Russell albeit for a negative reason (via Clutchpoints).
He became a footnote after Jerry Sloan sent him out to guard Jordan. This was like building a garden wall to keep out the ocean. It was a terrible call on the coach’s part but it also left Russell high and dry. He was helpless against Jordan’s brilliance in the latter’s final brilliant Bulls moment.
Technically, Russell Wilson was the man on the field who committed the error. But he was following Carroll’s orders as the Seahawks came within a breath of a Super Bowl win. Carroll infamously chose to throw the ball instead of handing the ball to Marshawn Lynch (via New Yorker).
Fans saw this as a career-defining mistake despite his previous Super Bowl victory. They couldn’t understand why he didn’t choose to give the marauding running back the ball. In the end, Malcolm Turner intercepted Wilson’s pass and the Patriots won the game. However, Carroll remains adamant that it was statistically the correct call at the time.
It took time for Karius to settle as Liverpool’s starting goalkeeper but he helped the team to a Champion’s League final. They met Real Madrid in the showpiece event but it became a living nightmare for the German. That’s because he made two massive mistakes in a career-defining performance that cost his team dearly (via DW).
First, he inexplicably rolled the ball directly to Madrid’s Karim Benzema. The Frenchman calmly slotted the ball home as Los Blancos took the lead. Later, he mishandled Gareth Bale’s shot and palmed the ball into his net. After the game, tests proved that Karius suffered a concussion during the match, but the career-defining moment still destroyed his career.
Larson was a top NASCAR driver with the Chip Ganassi Racing Team in 2020. Then he stained his career during an online race during the global health crisis. He didn’t realize that his microphone was live when he casually dropped a racist slur. NASCAR has a dubious reputation at best, so there was pressure to throw the book at him.
The driver’s team fired him because of his conduct but he bounced back with Hendrick Motorsport. It doesn’t appear to have damaged his long-term prospects because that’s how NASCAR works. But everyone now knows what type of person Larson is. He wasn’t sorry for what he said but rather just that the world heard him (via NBC News).
Sometimes athletes shoot themselves in the foot with a terrible decision. Burress took this to the next level by unloading his pistol into his leg inside a nightclub. The Super Bowl winner’s weapon went off and left him in agony as well as severe legal trouble. That’s because he didn’t have a license for the gun.
New York has some of the strictest gun laws in the nation and they threw the book at him. He spent 20 months in jail for his troubles and wasn’t the same player when he returned. It was a career-defining moment because he tarnished his legacy and damaged his prospects with one bullet (via Sportscasting).
Moss is one of the few athletes who came off on the good side of a bad decision. The running back had a terrible experience with the Oakland Raiders. However, this was mostly because of Art Shell and his inept coaching team. This was only a couple of years after a Super Bowl appearance but the team was in decline.
Shell’s offensive coordinator Tom Walsh claimed Moss was past his prime. But Moss proved the Idaho bed and breakfast owner wrong when they traded him to the New England Patriots. He was brilliant in Foxborough as he showed the league that he wasn’t finished en route to the Comeback Player of the Year Award. Moss set the single-season record most receiving touchdowns with 23 while playing with Tom Brady.
Darnold arrived in New York as the Jets’ latest great hope. Adam Gase believed he could get the best out of the young man. The head coach arrived after Peyton Manning recommended him to the franchise. However, Gase and Darnold completely failed at that task.
Arguably, Darnold’s worst moment came when he played against the Patriots and claimed that he was ‘seeing ghosts.’ These words haunted his career because the Internet instantly mocked him. Eventually, the Jets fired Gase and traded Darnold to the Panthers (via NFL.com).
Rousey was a force of nature during her early UFC career. Her opponents rarely made it out of the first minute let alone the first round. The former Olympic judoka arm barred her way to victory and became one of the first true superstars in MMA history (via Time).
Then she fought Holly Holm in a career-defining performance. The former kickboxing champion dissected Rousey on the feet in round one. Rousey went back to her corner for advice during the end of the round but her coach told her to keep boxing. It was a terrible error of judgment because Rousey suffered a vicious knockout and lost her title in a career-defining lapse.
Galarraga’s entire legacy suffered because of one terrible mistake. He was on course for a perfect game in 2010 when he was playing for the Detroit Tigers. The umpire admitted he made a horrible error and apologized directly to Galarraga afterward (via USA Today Sports).
Even The White House attempted to intervene to change the course of history. However, MLB refused to overturn the umpire’s decision because they didn’t want to set a dangerous precedent. The state of Michigan recognized Galarraga’s perfect game even if it didn’t enter the league’s official annals.
Terry remains one of the most polarizing figures in Premier League history. The former Chelsea captain was a brilliant defender but he created multiple controversies throughout his career. While it’s easy to attack his character there’s no denying his excellence on the field (via SportBible).
He led the club to the Champion’s League Final in Moscow against Manchester United. The game remained level after extra time and went to a penalty shootout. Terry stepped forward to take his shot but he slipped and miskicked the ball. People forget Nicklas Anelka also missed his shot because this moment became career-defining.
Baseball players earn a fortune in comparison to other Major Leagues. Gonzalez received a record-breaking offer in 1999 from the Detroit Tigers. They wanted to pay him a staggering $140 million extension but he rejected them. This proved to be a career-defining error because he missed a massive payday.
Gonzalez’s next season was poor and his stock instantly declined. In the end, the Tigers didn’t want him and he went to Cleveland. But the Indians only paid him $10 million for a single year. This proves that athletes must be pragmatic about contract situations because things can change very quickly (via Sportscasting).
Robinson won the NFL Bart Starr award in 1998 but he only held it for a day. The Falcons’ safety ruined his image by soliciting prostitutes in Miami. It wouldn’t have mattered if he didn’t speak to an undercover police officer. In the end, Robinson spent a sleepless night in a precinct cell.
Atlanta decided to play him the next day regardless but he didn’t perform well. Robinson received a lot of abuse after the game because fans knew what happened. He returned the Bart Starr Award because he didn’t feel that he deserved it. It was a moment of pure humiliation for the NFL star (via AP News).
Woodley was one of the best MMA fighters on the planet. Some people said the former welterweight champion was on course to eclipse Georges St-Pierre’s record as the greatest 170-pound MMA fighter ever. However, his UFC career came to an abrupt end and he wound up boxing YouTuber Jake Paul.
Paul defeated Woodley after a massive build-up and a boring bout. But the pair agreed to a rematch on short notice. This became a career-defining mistake for Woodley because Paul savagely knocked him out. It was a major indignity because of Paul’s lack of combat sports experience (via Draft Kings).
Gerrard’s story is one of the most tragic on this list because he was a brilliant servant for Liverpool. He came through the club’s youth ranks before captaining the team to glory. However, he never won the Premier League title with his boyhood team and arguably cost his team a long-awaited victory (via The Mirror).
The notorious career-defining moment came against Chelsea in 2014. Liverpool was ahead of Manchester City with a game in hand. Mamadou Sakho sent a weak backpass to Gerrard but the captain slipped as he attempted to retrieve it. Then Chelsea’s Demba Ba stole the ball and scored the goal that snatched Gerrard’s dream away.
‘The Butt Fumble’ remains one of the most hilarious and embarrassing moments in NFL history. It could only have happened to a Jets player because they endure the worst luck. Sanchez was a decent quarterback but failed to set the world on fire during his time with Gang Green (via USA Today Sports).
Then one play became a career-defining moment. Sanchez took the snap and faked a pass but the play broke down. Next, he charged forward as he tried to recover but ran face-first into lineman Brandon Moore’s behind. The Patriots retrieved the ball and immediately scored a touchdown to rub salt into Sanchez’s wounds.