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“Captured In His Pajamas”: 25 Of History’s Biggest Losers And How They Fell From Grace
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.
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#1
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.
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#8
Elon Musk is richer than anyone in history and still pays kids to pretend he's good at video games.
#9
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.
#10
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.
#11
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.
#13
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.
#15
Well the Vanderbilt family effectively lost almost all of one of the largest fortunes ever created in the United States. For some background:
Cornelius “Commodore” Vanderbilt died in 1877 with a fortune of about $100–105 million. Adjusted for inflation, that equals ~$2.5–3 billion today. Measured as a share of the U.S. economy (a more accurate historical comparison), historians estimate his wealth would equal ~$180–185 billion in today’s terms.
Basically offsprings went on an epic spending spree (and I mean an epic, highly suggest anyone interested to read more) and it’s all gone in less than a century.
EDIT: Actually factchecked and most was spend already between 1930-1950 and by 1970’s none of the 120 related people were millionaires.
#16
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.
#17
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.
#18
Me.
I’ve failed marriage, fatherhood, career, and overall life. Trying to recover, but doubt I will!
#19
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.
#20
Gotta be the guy who sold his Bitcoin for pizza back in the day. Now that's regret with extra cheese!
#21
Louis Klotz, founder of the Washington Generals who have a 6-17000+ record against the Harlem Globetrotters.
#24
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.
#25
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.
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