13. Warren G. Harding Second Offense
When it comes to affairs, like the behavior of thieves, there is rarely one incident. Before Harding was president, Warren Harding maintained a regular affair with a woman named Carrie Fulton Phillips. The affair carried on until he started his bid for the presidency. Phillips tried to blackmail Harding over the affair, which put the last nail in the coffin of their affections. To undermine her efforts, Harding confessed to his party, the Republicans in 1920.