Highest Office Held: Queens Borough President

If you thought Rod Blagojevich was the first to try to sell a position of high power, you thought wrong. Cassidy was up to a whole lot of shady business while he was Queens Borough President, using his power to make a killing in real estate. But his real low-point came after leaving office.

Even after he was accused of 47 counts of financial impropriety and indicted for 24 of those charges, he still held serious sway in the game. Cassidy attempted to sell a seat on the New York Supreme Court to William Willet, which finally landed Cassidy a well-deserved one-year term in Sing Sing.