The 16 Biggest Political Losers

George McGovern

Who Is He? Former US Senator for South Dakota

McGovern began as a congressman for the first district of South Dakota in 1957. He eventually became a senator for the state and held that office for nearly 20 years. He attempted to run for president twice but failed and decided to try his hand at business by opening a hotel in 1988.

Joe Seer /

Joe Seer /

After just four years, he had to file for bankruptcy proving that the transition from politics to business is not any easier than the transition from business to politics. He would later state that his experience with bankruptcy and debt would have made him more sympathetic to American business owners as a politician.

Donald Trump

Who Is He? Real Estate Magnate, GOP Presidential Candidate

Donald Trump is remarkable not for his success in business but for his utter inability to go totally broke despite actually being quite terrible at handling money and making smart business decisions.


His companies have declared bankruptcy 4 times and while he claims to be worth about $9 billion, Forbes’ own investigation put his net worth at no more than about $125 million.

After a slew of scandals during this most recent primary campaigning, he’s lost multiple business contracts including a Trump clothing line at Macy’s, the NBC reality show, The Apprentice, and multiple networks cancelling their scheduled airing of Trump’s Miss Universe Organization beauty pageants.

lev radin /

lev radin /

For a man likely worth significantly less than he claims, he’s sure willing to lose a lot of money. The 3 lost contracts above total about $50 million together which would bring the Forbes estimate of his net worth down to just $75 million.

Tom McMillen

Who Is He? Former US Congressman for Maryland

Tom McMillen is a jack of all trades. Before politics, he was a professional NBA basketball player for the Buffalo Braves. He gave up a life of fame and luxury for a life of bureaucracy and legislative debates in 1986. That was probably the first major bad decision.

He failed to get reelected in 1993 but he will forever be remembered as the tallest congressman. As you know, height is a very important quality in politicians. Being tall failed to prevent him from filing for bankruptcy in 1992, though.

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