The 16 Biggest Political Losers

Benedict Arnold

Who Is He? Former Army General

Benedict Arnold enjoyed fighting the Revolutionary War so much, he fought for both sides. He started out in the American Army but eventually switched over to the British Army, officially making the name “Benedict Arnold” synonymous with “traitor” for the rest of U.S. History.

What few people learn is that the reason he defected to the British is because he was deeply indebted to the US Congress. The British paid him nicely, despite his failure to actually carry out the secret plot they had concocted to bring down the American Army. After the war, he moved to London where he would continue to build up more debt and never pay it off until the day he died.

Everett Historical /

Everett Historical /

Failing to keep promises was apparently his one and only skill.

Anne Cox Chambers

Who Is She? Media Proprietor, Stakeholder in Cox Enterprises


Cox Chambers is one of the mega donors on the Democratic side. The billionaire is worth $17.3 billion. At 95 years young, she is one of the oldest billionaires in the ranks today.

But being a billionaire doesn’t exclude you from the potential to lose big. This year, she’s watched her enormous pile of money shrink by $1.3 billion. The loss came after a decline in her public competitors. Needless to say, she hasn’t been as generous with her campaign dollars this year.

Abraham Lincoln

Who Is He? Former President of the United States

Abraham Lincoln was our 16th and probably most famous president—after George Washington, perhaps. As we are learning from this list, though, no one is exempt from the consequences of being terrible at handling money. You’re probably checking out financial management courses right now to avoid meeting the same fate as these people.

Lincoln met his financial ruin long before he’d become president. In 1832, he bought a general store on credit. Although the economy was strong at the time, he could not manage to turn a profit and ended up filing for bankruptcy. He would spend the next 20 years paying off the debt from that fiasco.

Everett Historical /

Everett Historical /

In 1834, he would turn to politics, realizing that maybe business was not his strong suit. In 1835, he would attempt to pass a bill that would provide relief for debtors—that is, relief for himself—but it didn’t pass and he would have to continue making payments.

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