Dick Cheney – $100 million

46th Vice President to President Bush, Dick Cheney, is often cited as “the most powerful V.P.” in history. His long and controversial career within the Democratic Party has made him an unpopular figure in American politics. 

Most of his $100 million wealth came from his post as CEO and chairman of the board for the oil service contractor Halliburton from 1995 to 2000. When Cheney left to join Bush’s administration in 2000, he won an early retirement package estimated at $20 million. In 2018 Christian Bale portrayed the political figure in a biopic made about his life, directed by Adam McKay.