7. Gary Condit: The Ice Cream Man
Highest Office Held: US House of Representatives, California
After the disappearance of his one-time mistress Chandra Levy, Gary Condit's political career was as good as dead. Though he was not asked to vacate his Congressional seat as a result of the scandal, he did lose his bid for re-election. So, Condit did the only sensible thing and bought into some Baskin-Robbins franchises in Phoenix. This didn't end well.
The Condits lost several legal battles with Baskin-Robbins, resulting in hefty penalties against the family that only grew larger when Gary elected to not show up for court dates. While attempting to stave off Baskin-Robbins's debt collectors, Condit sued numerous news outlets for libel stemming from the Levy scandal. All but one of these defamation of character suits was dismissed. The judges felt that Condit was doing a pretty good job of defaming himself by that point.