In a uniquely personal episode, Jake unpacks the "Appalachian Trail" scandal of his friend and former South Carolina Governor Mark Sanford and explores the difference between the politician and the man underneath.

In 2008, the Sheriff of Wall Street, New York Governor Eliot Spitzer, imploded spectacularly when he was revealed to be the infamous Client 9 during a sex worker sting operation. Jake charts the rise and fall of a potential president with Spitzer's former mentor and closest friend.