Learning To Lose: 15 Of The Toughest Losses In Sports

There’s nothing more American than professional sport. We love our sports and we have plenty of them. Ever since we are young, were encouraged to play a sport and overtime we grow to love the sport that we play whether it’s baseball, basketball, football, hockey, soccer, tennis, and the list goes on and on. We love sports because of what they teach us and how they mould us, but unfortunately when playing competitively there always needs to be a winner and a loser. And sometimes winning is a whole lot easier than losing- especially when the losses are crushing. Absorbing crushing losses doesn't get easier the older you get- they only sting more and tend to last longer. They aren't done in front of family and friends anymore but in front of 16,000 screaming fans and millions more watching from their homes. So, what constitutes a crushing loss? Any loss that is so unexpected it leaves the player or team devastated and reeling for months and even years later. Some losses can impact a a team, city, and and it’s fans for several years. The memories hover over the arena and leave a city feeling deflated and defeated. With this list, well measure the agony of defeat against the thrill of victory that caused it. The 15 Toughest Losses in Sports History will also relive some of sport's most classical moments.

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15 Tony Romo Botches the Hold

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In 2007, Dallas Cowboy quarterback, Tony Romo, only needed to catch a snap and place-hold the football for his kicker to nail a 19-yard field goal attempt against the Seattle Seahawks in the NFC Wild Card playoff game. The kick would have won the game and advance the Cowboys into the next round. Trailing by one with the score 21-20, and 1:19 left on the clock, the Cowboys faced fourth-and-one. They sent in the kicker and the snap was good but Romo bobbled the snap and tried to run it in himself- only to be tackled on the two-yard line. Seattle went on the win the game, and Romo’s reputation as a choke artist when a big game is on the line was etched in stone. Though often near the top of NFL quarterbacks in terms of passer ratings in the regular season, Romo has only been able to win two playoff games with the Cowboy throughout his 16 year career.

14 John Carney Misses

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There is perhaps no greater pressure situation than kicking a field goal to tie or win a game. But while quarterbacks get all the glory, place kickers carry all the blame when their kick misses the mark. This is what happened to John Michael Carney while kicking for the New Orleans Saints. As a Saints took on the Jacksonville Jaguars on December 21, 2003, they trailed by a touchdown 20-13. The final moments were set up by an infamous play known as the "River City Relay." It required the Saints to use three lateral passes to score a touchdown just as time expired. All Carny needed to do was kick the extra point through the uprights and send the game into overtime. But Carney watched as his extra-point attempt sailed wide-right. The shocking moment was captured by Saints play-by-play radio announcer Jim Henderson, who screamed into the microphone, “NOOOO! He missed the extra point wide right! Oh my God, how could he do that?” Though they missed the playoffs that year, they won the 2004 ESPY Award for Best Play thanks to the Relay.

13 Bill Buckner Blunder

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Baseball is a very superstitious sport and throughout its history it’s had it’s share of famous ones. Some involve the playing field such as stepping over the foul line, while others involved teams like “The Curse of the Billy Goat” which is attached to the Chicago Cubs. Then there was “The Curse of the Bambino” placed upon the Boston Red Sox for trading one of the greatest players to ever live- George Herman “Babe” Ruth Jr. During the 1986 World Series against the New York Mets, the Red Sox were well on their way to break The Curse when a slow dribbler down the first base line changed everything. Red Sox first baseman, Bill Buckner, was hobbled by chronic ankle soreness yet allowed to stay in the game by Red Sox skipper John McNamara. Concerned with Met’s batter Mookie Wilson’s speed, Buckner tried to hurry the play which resulted with Wilson’s slow roller going off his glove, through his legs, and into right field. The Mets scored the winning run and the series in one of the most improbable comebacks in World Series history.

12 The Music City Miracle

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This ending might sound like fun unless you’re a Buffalo Bills fan. But for those familiar with the play know it as one of the most shocking endings to an NFL playoff game ever. On January 8, 2000, the Tennessee Titans took on the Buffalo Bills in a see-saw Wild Card game played in Tennessee. The Bills had scored what appeared to be the game-winning field goal when Steve Christie nailed his kick from 41 yards with only 16 seconds left to play. Down 16-15, Tennessee received the kickoff and proceeded to run a play they called “The Home Run Throwback.” It called for the kick receiver to hand the ball off to Frank Wycheck- would then threw the ball across the field to Kevin Dyson. Dyson caught the ball and ran 75 yards to the end zone for the score. After a long and lengthy review, officials finally determined the play legal, and awarded the Titans the touchdown. They went on to win the game 22-16. What sparked even more controversy was Bills head coach Wade Phillips’s decision to start quarterback Rob Johnson over Doug Flutie, who had started 15 games and led the team to the playoff game.

11 Ewing’s Missed Layup

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Playing in New York is definitely no walk in the park. Include being the number one Draft Pick of the NBA’s first-ever lottery, and the saviour of a franchise badly in need of a title and you have Patrick Ewing. Ewing was the New York Knicks center during the '80s and '90s and “the guy” who was going to bring a title to New York. They even hired former Laker coach Pat Riley to ensure it happened. But when they failed to win the NBA Finals the year prior, expectations were at epic levels. Then on May 22, 1995, it all came crashing down. The Knicks were facing their bitter rivals- the Indiana Pacers (led by nemesis Reggie Miller). Ewing played well throughout the series- even hitting a game winner in Game Five with 1.8 left. But his Game Seven missed finger-roll lives in infamy. With a chance to tie and send the game into overtime, Ewing took an inbound pass and instead of dunking it, tried to lay it in. He missed and the Knicks were eliminated from the playoffs. Riley left the team after the loss and Ewing never brought a championship to the Garden.

10 The Fumble

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Football fumbles happen all the time, but when you mention “The Fumble,” it’s in reference to the 1987 AFC Championship game between the Cleveland Browns and Denver Broncos. The game was played in 1988 at Denver’s Mile High Stadium where the Broncos were up 38-31 with only six minutes left. They had jumped to an early 21-3 halftime lead, but then the Browns came storming back behind quarterback Bernie Kosar to keep the game close. Going for the game-tying score, Browns running back Earnest Byner appeared to be headed toward the goal line, only to get stripped by Broncos defensive back Jeremiah Castille. The Broncos pounced giving the Browns a safety instead of a much-needed touchdown. The game end 38-33 and “The Fumble” had gone on to exemplify Cleveland’s lack of futility and fan’s long suffering misery until Lebron James brought a title to Cleveland in 2016. The Cavs title win ended one of the longest droughts for a major sports city.

9 Chris Webber’s Costly Timeout

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Chris Webber’s timeout blunder will always be remembered as one of college sports most memorable moments. He was part of the Michigan Wolverine’s "Fab Five," which also consisted of fellow future NBA players, Jalen Rose and Juwan Howard, who were trying to avenge their championship loss to Duke the season prior. Taking on Dean Smith’s North Carolina Tar Heels in New Orleans for the 1993 NCAA Championship game, they played it fairly close and the game came down to the closing moments. That's when Webber corralled a rebound and raced down the sideline. Down by two (73-71) with only 20 seconds left and surrounded by a sea of power-blue jerseys, Webber called for time out. The problem was Michigan was out of timeouts and the Wolverines were issued a technical. The Tar Heels won the game and sadly, Webber’s collegiate basketball career ended that day. Though he played well (23 points, 11 rebounds, and three blocks), he’ll mostly be remembered for that single blunder in New Orleans.

8 The Pats Almost Perfect

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The 2007 New England Patriots were well on their way to becoming the first team to finish an entire season undefeated since the 1972 Miami Dolphins and only the New York Giants stood in their way to perfection. Dominant during the regular season, the Pats ran over opponents with intention trying to avenge their AFC Championship loss to their rivals, the Indianapolis Colts, in the playoffs. The Giants meanwhile, were heavy underdogs going into Super Bowl XLII having limped into the playoff as a Wild Card team. It took one of the most memorable catches in Super Bowl history-Eli Manning to David Tyree, who made a leaping, one-handed catch against his helmet for 32 yard gain to keep the Giant’s hopes alive. Manning’s touchdown pass to Plaxico Burress sealed the victory a few plays later giving the Patriots their only taste of defeat in front of a Super Bowl record 97.5 million US viewers.

7 Norwood Misses Wide Right

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Scott Norwood was a Buffalo Bills placekicker for six years, making the Pro Bowl in 1988. Few know that Norwood once led the NFL in scoring and played in two Super Bowls- both with the Bills. What he’s best known for is the kick he didn’t make; a wide-right field attempt from 47 yard out in Super Bowl XXV. Facing the New York Giants on January 27, 1991 at Tampa Stadium, the Bills were locked in a low-scoring affair when Bills quarterback, Jim Kelly led the them down the field in their final possession. With eight seconds left, down 20-19, and the ball on the Giants 29 yard line, Norwood’s booted football sailed less than a yard outside the upright goalpost- giving the Giants the Super Bowl victory. The loss was devastating to Bills fans and players and Norwood was waived after the following season. After leaving football, Norwood disappeared completely from the public eye for several years.

6 The Cubs and Steve Bartman

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If you google the words “Cubs Infamy” one of the very first pictures you’ll see is the play involving Cubs fan, Steve Bartman. Bartman thrusted himself into infamy when he attempted to catch a foul ball during the 2003 National League Champion Series, which turned out to be a very crucial moment. The long-suffering Cubs were up 3-0, over the then Florida Marlins, in Game Six at Wrigley Field. All they needed to advance to the World Series were five outs when the Marlins Luis Castillo hit a pop-up down the left-field line towards the seats. Cubs leftfielder Moises Alou, tracked the ball and attempted a play on it until Bartman interfered leaving Alou clearly frustrated and yelling towards him. Castillo walked, and the next batter delivered a run-scoring single. By the time the inning ended, the Marlins had scored eight runs to take an 8-3 lead and eventually the series. Fearing for his safety, Bartman was escorted out of Wrigley Field and was never seen in public again.

5 Bill Mazeroski Sinks The Yankees

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Walk-off World Series home runs are perhaps the greatest moments of the game and baseball’s had a few of them. Kirk Gibson’s 1988 homer vs. the Oakland A’s, and Joe Carter of the Blue Jays left-field dinger against the Philadelphia Phillies. But, before those moments of greatness, there was Bill Mazeroski’s home run against the New York Yankees. “Maz” as he was known, was a great defensive second baseman. Some even argue he was the greatest second baseman to ever play the game, so when he stepped up to the plate, few expected him to do what he did. He hit one of the greatest home runs in Major League history and the only Game Seven World Series walk-off in World Series history. His homer ended the Yankees domination and began their sharp decline. They fired manager Casey Stengel, and many of their stars began to age- ending baseball’s first true dynasty and one of the greatest teams in baseball history.

4 Jordan Over Ehlo

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Michael Jordan is undoubtedly the greatest basketball players ever to lace up a pair of Nikes. But, Jordan needed to begin his legacy somewhere, so he chose Game Five of the 1989 Eastern Conference playoffs. Jordan’s Bulls took on the Cleveland Cavaliers- who owned the Bulls during the regular season, going 6-0 against them. It was Jordan’s sixth year in the league and he had yet to be on the winning end of a playoff series. The third-seeded Cavs had little reason to believe they wouldn’t advance versus the sixth-seeded Bulls. That changed when Jordan took an inbound pass from Brad Sellers and in spite of being double-teamed by Craig Ehlo and Larry Nance, drained a jumper from the foul line. The moment was immortalized for those watching at home by the announcers who yelled, “Here's Michael at the foul line, the shot on Ehlo...GOOD! Bulls win! GOOD! THE BULLS WIN IT! THEY WIN IT!”

3 The Angels One Strike Away

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Baseball is full of heart-breaking losses due to the fact that one pitch can decide an entire series- if not an entire season. Such was the case with the California Angels and Boston Red Sox. The game took place in Anaheim on October 12, 1986 during the American League Championship Series. Angels All-Star closer, Donnie Moore came in to pitch with the Angels needing only one out and were one strike away from advancing to the World Series for the first time in the franchise’s history. The Red Sox’ Dave Henderson was able to hit a 2-2 pitch for a home run to take the lead, which the Angels tied, sending the game into extra-innings. Staying in the game, Moore was able to keep pace until giving up a sacrifice fly in the 11th inning. The Angels failed to score and lost the game and eventually the series. The Red Sox would eventually suffer their own heart-breaker to the New York Mets.

2 Soviet Union Defeats Team USA in Basketball

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Before MichaelJordan, Larry Bird, Patrick Ewing and Magic Johnson decided to take over Olympic basketball and reset expectations for future teams. There was the 1972 Team USA Summer Games heart-breaker in Munich, Germany. Down by one, a young Doug Collins, age 21, was fouled and stepped to the foul line with three seconds left to calmly drained both free-throws. As the Russians in bounded the ball, the Soviet coach tried frantically to call for a time out and jumped onto the court with the clock winding down- forcing the referee to stop play. What preceded next was a comedy of errors between referees, shot clock officials, and both teams. The Russians in bounded again, and missed a long shot beyond half court- sending the Americans into celebration as the horn sounded. But the game still wasn’t over. The clock was never reset properly and the players were forced back onto the court. In their haste to return, the U.S. left reserve 7’2 center Tom Burleson on the bench instead of guarding against the long pass. This allowed 6’7 Russian Aleksandr Belov to score off the long inbound pass for the upset. In spite of two protests, the Americans were denied and never accepted their silver medals.

1 Tyson Loses for the First Time

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“Iron” Mike Tyson was “the baddest man on the planet” in 1990. Dressed in his trademark all-black, Tyson entered the ring in Tokyo, Japan as a 75-1 favourite. Few expected his fight with Buster Douglas to last past two rounds. But fighting under the shadow of his recently deceased mother, Douglas went toe-to-toe with Tyson- even absorbing some of his blows. That allowed him to survive until the eigth round when Tyson caught him with a right uppercut which sent him to the canvass. After a long nine count, Douglass got to his feet and was saved by the bell. In the tenth, Tyson, under a flurry of blows, was clearly in trouble. Douglas kept up the pounding and floored Tyson for the very first time in his unbelievable career. Tyson fumbled for his mouthpiece in an attempt to get back up, but referee Octavio Meyran had seen enough and counted him out. Buster Douglas became the new Heavyweight Champion of the World and the fight is still regarded as one of the biggest upsets in sports history.

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