The history books are full of stories about the world’s greatest winners. But what about those who came and saw and failed spectacularly? The ones who lost wars, money, friends, their reputation and sometimes, their dignity…
People like Elon Musk , who made it into the Guinness Book of World Records in 2022 as the biggest loser (of personal fortune) ever. Or a British couple, who celebrated an incredible £182 million lottery ticket win, only to discover their bank hadn’t made the transaction for the ticket due to a lack of funds. Ouch.
While it’s never nice to celebrate anyone’s misfortunes or losses, some are just so legendary that they need to be noted. And that’s possibly why a curious soul recently asked , " Who is the biggest loser in history? "
Bored Panda has gone through almost 2,000 responses to put together a list of the best ones. May they help you to feel a whole lot better about your own shortcomings.
Hmmm. Riddle me this: Who filed for bankruptcy six times (Including for his casinos which basically print money), has dozens of failed business ventures, was convicted of fraud 34 times, was impeached twice, has a speaking grade level between 4th grade and 7th grade, cheated on all of his wives, has narcissistic personality disorder, cheats on his taxes, is racist and sexist, bullies people, threatens people and is actively seeking to destroy the world order? Hmmmm. I’ll have to think about my answer.
The_Spyre , White House Report
Elon Musk. Even Epstein thought he was a loser.
-Galahad- , NORAD and USNORTHCOM Public Affairs Report
Anybody with a net worth of 1B+ who has not chosen to become Batman.
dope-rhymes Report
US citizens, a nut job was given the steering wheel twice.
Tsperatus Report
Jared from subway. Biggest loser in weight, but an even bigger loser in morality.
Ziggy396 , Anna Hanks Report
Anyone who bought NFTs.
BornSlippy69 Report
The guy at Decca who rejected the Beatles claiming that there wasn’t a taste for boy bands.
FeistyPhone9351 , Capitol Records Report
Elon Musk is richer than anyone in history and still pays kids to pretend he’s good at video games.
BritChap42 , Elon Musk Report
General Santa Anna was so cocky during the Texas Revolution that he let his army take a siesta without any scouts. He was captured in his pajamas, forced to sign away Texas, and eventually lost half of Mexico’s entire territory to the U.S.
Maverick_Ekta , SMU Digital Collections Report
The people to put all their money into the Huak Tuah meme coin that cratered in like 10 minutes and effectively ended her 15 minutes of fame.
cpatkyanks24 , Tim & Dee TV Report
The guy who decided to wage war against Russia during the winter. Not learning from past war decisions. Never go full scale during the winter.
PorkyPain Report
Ronald Wayne. Along with Steve Jobs and Steve Wozniak, one of the founders of Apple Computer. He didn’t think it would work out, so he left the company early and cashed out his shares.
bflaminio , Unknown Report
Australian army. Lost a war to emus in 1932. 986 emu lives lost. 1 nations ego died.
No-Distance-2124 , Unknown , The Land Newspaper Report
Thomas Midgely Jr. he invented CFCs and leaded gasoline.
NotNinjalord5 , Blank & Stoller N.Y. Report
Dokkeri , Seymour Joseph Guy Report
William Topaz McGonagall is considered the worst poet in history. The only way he could people to listen to his poems was when he was hired by the circus and allowed to be pelted with rotting fruit while reading his work.
777Void777 , The Independent Report
The UK couple who thought they had won £182M in the lottery only to find their bank hadn’t made the transaction for the ticket due to a lack of funds.
EricaRA75 , Erik Mclean / Unsplash (not the actual photo) Report
Me. I’ve failed marriage, fatherhood, career, and overall life. Trying to recover, but doubt I will!
SylvesterCross Report
Masayoshi Son, the founder of SoftBank, is often cited as the individual who lost the most money on paper in history. During the dot-com crash of 2000–2001, his personal net worth fell by an estimated $70 billion as tech valuations collapsed. Despite the staggering loss, he rebuilt his fortune and remains one of the most influential investors in global technology.
jordanpatrich Report
Louis Klotz, founder of the Washington Generals who have a 6-17000+ record against the Harlem Globetrotters.
cityofpalms Report
Gotta be the guy who sold his Bitcoin for pizza back in the day. Now that’s regret with extra cheese!
cloudcontinuum- Report
Nick Leeson - a single bad stock trade collapsed Britain’s oldest bank.
jacobid , Johnny Savage/The Guardian Report
Anthony Young, a NY Mets pitcher who lost 27 consecutive games .
TheAcmeAnvil , Bill Pucko Report
Michael Ballack wasn’t a loser because he lacked quality. He was one because football kept denying him the final reward. It began in 2000: playing for Bayer Leverkusen on the final matchday, Ballack scored an own goal against Unterhaching — a single moment that turned a title race into heartbreak and gifted Bayern Munich the championship. 2002 alone, he lost the Bundesliga title on the last matchday, the German Cup final and the Champions League final. At the 2002 World Cup, Ballack dragged an otherwise limited German side into the final with decisive goals — then watched the biggest match of his career from the stands due to suspension. Germany lost. Four finals. Zero trophies. Six years later, history repeated itself. As captain, Ballack led Germany to the Euro 2008 final, only to lose again — this time to Spain’s emerging golden generation. And then came 2010: another cruel twist. A brutal injury ruled him out of the World Cup entirely. Germany went on to reach the semifinals without their leader, leaving Ballack as the absent face of what might have been his last chance at redemption. Ballack was a world-class midfielder stuck between eras: too late for Matthäus’ titles, too early for the 2014 World Cup generation. He led strong teams — just never legendary ones.
gollinho Report
Hillary Clinton..lost to Obama in 2008…struggled to beat Bernie for the nomination in 2016 (with considerable help from the establishment) Lost to Trump in 2016. Beaten twice by political neophytes and nearly lost the nomination to a man who isn’t even a Democrat.
Willing_Crazy699 Report
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