The 16 Biggest Political Losers

Jesse Jackson, Jr

Who Is He? Former US Congressman in Illinois

The son of a former US Shadow Senator—an unpaid job which sounds way cooler than it is, trust me—Jess Jackson, Jr decided to follow in his father’s footsteps by taking office in 1995. In 2012, the FBI started investigating him for potential fraud. By 2013, he had plead guilty to mail and wire fraud. It turns out he had used $750,000 in campaign funds for personal use.

Now, if you’re thinking that “personal use” must have been something sinister and corrupt, guess again. He was essentially using the money for shopping sprees. Essentially, he served 2 years in prison for buying a Michael Jackson fedora and a bunch of cashmere capes. Yes, you read that correctly: cashmere capes. You’ll be hard pressed to figure out even one single occasion in which it would be appropriate to wear a cashmere cape, except perhaps fighting really high-end, luxury crimes, maybe. But even then, do you really need more than one cashmere cape for that?

Joseph Sohm /

Joseph Sohm /

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