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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.
This post may include affiliate links.
#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.
Robyn Hill 2 days ago
Don't forget all the allegations in the Epstein files, his own admissions about grabbing women by the __ and committing s****l a*****t on them, and oh yes, macking on his own daughters.
StrangeOne 2 days ago
Just the fact that he was allowed to run for any political position in the first place both answers a lot of questions about the mentality of the USA and leaves some disturbing questions I'm not sure I want to know.
antoinette maldari 2 days ago
I guess we (The People) should add another condition to the eligibility to become President-NO FELONIES! I'm surmising that out Fore Fathers left that condition out thinking who in their right mind would run if they had a rap sheet and even more bizarre is who the fuckel would vote for them. 250 years later, we have the answers.
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Multa Nocte 2 days ago
Now that I see this is an option, I may have to go back and downvote my own answers for Elon being number 1.
KatSaidThat 2 days ago
The problem with that is that he dies a martyr and gets state funeral. And then Vance takes his place. I now understand why all the different agencies are making sure he is not in fact assassinated and dies by his own sword instead.
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TACO Don's Authentic TexMex 2 days ago (edited)
I've come to believe that MAGA is a learning disability. Those stupid felon worshipping cultists defending that pedophile in the comments are proof. Can you imagine seeing an old convicted felon that s***s his pants on camera and paints his face in bright orange makeup every day and being like "yeah, that's who I'm going to dedicate my very existence to"? How f*****g pathetic are those felon worshipping mouth breathers? Can you imagine being so pathetic you willing let yourself be cucked by an old man in diapers and orange face paint?
Emilu 1 day ago
Don't give them ideas; they'll probably try and use it as a reason to get social security or something.
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Pferdchen 2 days ago
He is truly a despicable person and the world would be a better place if he had never been born. On the other hand, he hasn't spent a single day in jail or otherwise paid any real penalties for all of his egregious actions, including extorting bribes totaling over a billion dollars while in office. I suspect all of those strategic bankruptcies occurred after he drained all the equity out of the businesses and avoided paying the debts and contractors. Given this, I think "master criminal" might be more appropriate than "biggest loser."
Nicole Weymann 2 days ago
I think the key to his success IS the narcissist personality. The rasoning seems to be "He's so sure of himself, he is quick at making decisions, pro active, not a dawdler. So competent!" All the while ignoring that he's so sure because he blithely ignores everyone and everything not to his liking - including facts - and where ignoring doesn't work he'll shout louder so nobody hears anything bus his voice. Narcissist shine like the sun, blinding others, because to them they are the only relevant factor in any and all affairs.
Virgil Blue 2 days ago
You got it. My therapist explained it pretty much like that to me, they are kind of a parasitic mind that warps others perception of them and uses their talents to seem better themselves. It was when we where exploring my troubles with my dad who also has consumed a sizeable slice of the narcissism cake. Not as bad as Trump though. Just imagine. Man. Good grief. The thing is that under that glamour (in the classic sense) they are a kind of incomplete damaged soul. But one you can't pity or help because they will eat you whole, practically on instinct.
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Robert T 2 days ago (edited)
You missed "f***ing idiot" with a room temperature IQ measured in Celcius!
Virgil Blue 2 days ago
People that narcissistic often are. They can't develop properly because they lack the self reflection that leads to self improvement. The successful ones almost instinctively dupe people into thinking they must be intelligent to be that confident and work with them in the hope of "profiting" of that fake genious and end up keeping them and their legend afloat.
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meeeeeeeeeeee 2 days ago
rapist, rapist of children, s***s Bill Clinton's d**k but hates gay people...etc, etc, etc
Brandi VanSteenwyk 2 days ago
Trumpaloompa would also lead any list of the "Most Embarrassing People in History". I have never, ever prayed for an individual's personal destruction/death more than I have for Trump's demise.
Multa Nocte (she/her/8647) 1 day ago
He's a loser. LOSER. Big fat unpatriotic traitorous loser. Get over you adoration of this rapist pedophile and use your brain.
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Multa Nocte (she/her/8647) 1 day ago
Fuck off, Wheeskers, you loser. You're one of the loyal stasi, but you are a traitor to the United States.
Load More Replies... TACO Don's Authentic TexMex 2 days ago (edited)
And as always we have a single digit IQ mouth breathing pedophile worshipper defending their orange painted god. I feel so sorry for you MAGAt freaks, so stupid you don't even know you've been conned by a felon in orange face paint. You felon worshipping cucks have got to be the most moronic and pathetic creatures in existence. You hardly qualify as human at this point
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RELATED:
#2
Elon Musk. Even Epstein thought he was a loser.
Farah (she/her) 2 days ago
Imagine begging to go to that island where EVERYONE was and epstein just saying "umm no"
#4
US citizens, a nut job was given the steering wheel twice.
#5
Jared from subway. Biggest loser in weight, but an even bigger loser in morality.
Nathaniel He/Him Cis-Het 2 days ago
If only he was a billionaire, then he would have rich and powerful friends to do business with despite being a nonce.
#6
Anyone who bought NFTs.
Luke || Kira (he/she) 2 days ago
I really have to laugh at all those cryptobros smugly flaunting their hideous monkey pictures, thoroughly CONVINCED they'll be worth millions.
#7
The guy at Decca who rejected the Beatles claiming that there wasn’t a taste for boy bands.
StPaul9 2 days ago (edited)
Decca went back and signed Gerry and the Pacemakers and George recommended some band called The Rolling Stones to them. That band is going good. What is also not said is that the Beatles auditioned with some cover versions (only three Lennon-McCartney songs), and he just didn't see them as original.
#8
Elon Musk is richer than anyone in history and still pays kids to pretend he's good at video games.
Multa Nocte 2 days ago
Yeah, that was weird to read about. If I had that much money I believe my ego would be a little stronger.
#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.
Ace 2 days ago (edited)
I'm reminded of the Asterix in Britain comic book, where the Romans manage to conquer Britain by using the jolly unsporting tactic of attacking while the Brits had stopped for their afternoon tea break. (Actually, it was just hot water, part of a running gag with things like "spot of milk in your hot water, old chap?" ending up with some herbs being used to create a fake magic potion which turned out to be tea).
#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.
Robyn Hill 2 days ago
He also failed to listen to his generals when they had the BEF cornered at Dunkirk . . . wonder how that turned out for him?
#12
Australian army. Lost a war to emus in 1932.
986 emu lives lost.
1 nations ego died.
#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.
#22
Nick Leeson - a single bad stock trade collapsed Britain’s oldest bank.
Did I say that out loud? 2 days ago (edited)
No,it wasn't a single bad trade. It was lots of them. Edit to add. He was basically like a very bad gambler chasing his losses but getting further and further behind. But, because he was able to convince his bosses back in London that he was actually making shít loads of money there was no proper oversight until it was too late. Can you imagine,bank bosses being so greedy they forget the old saying about if something seems to good to be true.....?
#23
Anthony Young, a NY Mets pitcher who lost 27 consecutive games .
Did I say that out loud? 2 days ago
Was he playing the opposition all on his own then? What were his teammates doing?
#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.
What do you think ?
Nota Robot 2 days ago (edited)
I wouldn't say it's important to learn from failures, I d say it's important to show who they really are. Look through the money and the glamour.
TheForrestGreene (he/they/it) 1 day ago
In my opinion, the biggest loser is that guy from the pokemon anime who left his charmander in the rain to die because "it was too weak"
John Monteith 1 day ago
Gerald rather. Who the rather effect was named after. Look it up. He said his jewellery chain stuff was c**p. Tanked the company.
Nota Robot 2 days ago (edited)
I wouldn't say it's important to learn from failures, I d say it's important to show who they really are. Look through the money and the glamour.
TheForrestGreene (he/they/it) 1 day ago
In my opinion, the biggest loser is that guy from the pokemon anime who left his charmander in the rain to die because "it was too weak"
John Monteith 1 day ago
Gerald rather. Who the rather effect was named after. Look it up. He said his jewellery chain stuff was c**p. Tanked the company.
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