25 Historical Figures Widely Considered To Be Some Of The Biggest Losers

Throughout history, people have celebrated champions who won wars, built strong economies, or became powerful forces to reckon with. These winners dominate our stories, but we rarely discuss those who tried and failed. They not only lost wars and wealth, but also suffered lasting damage to their reputations because of these spectacular failures. Today, we’ve compiled a list of some of history’s biggest losers, based on the opinions of Redditors who responded to the question, “Who is the biggest loser in history?”

#1

Image source: Ziggy396, Anna Hanks

Jared from subway. Biggest loser in weight, but an even bigger loser in morality.

#2

US citizens, a nut job was given the steering wheel twice.

Image source: Tsperatus

#3

Image source: Maverick_Ekta, SMU Digital Collections

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.

#4

Image source: -Galahad-, NORAD and USNORTHCOM Public Affairs

Elon Musk. Even Epstein thought he was a loser.

#5

Image source: The_Spyre, White House

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.

#6

Anybody with a net worth of 1B+ who has not chosen to become Batman.

Image source: dope-rhymes

#7

Anyone who bought NFTs.

Image source: BornSlippy69

#8

Image source: cpatkyanks24, Tim & Dee TV

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.

#9

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.

Image source: PorkyPain

#10

Image source: FeistyPhone9351, Capitol Records

The guy at Decca who rejected the Beatles claiming that there wasn’t a taste for boy bands.

#11

Image source: Dokkeri, Seymour Joseph Guy

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.

#12

Image source: cityofpalms

Louis Klotz, founder of the Washington Generals who have a 6-17000+ record against the Harlem Globetrotters.

#13

Image source: NotNinjalord5, Blank & Stoller N.Y.

Thomas Midgely Jr.

He invented CFCs and leaded gasoline.

#14

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.

Image source: jordanpatrich

#15

Image source: bflaminio, Unknown

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.

#16

Image source: EricaRA75, Erik Mclean / Unsplash (not the actual photo)

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.

#17

Image source: No-Distance-2124, Unknown

Australian army. Lost a war to emus in 1932.

986 emu lives lost.

1 nations ego died.

#18

Image source: 777Void777, The Independent

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.