Amassing a large personal fortune as a political wheeler-dealer, McAuliffe used his various positions to raise funds for politicians and to expand his political network. There is no line between personal business deals and politics for McAuliffe. He once said “if the worst thing you say about me is ‘Terry McAuliffe has done business with people he’s met through politics,’ so be it. I plead guilty.”
McAuliffe’s litany of politically connected businesses started with his failed tenure as Chairman of Federal City National Bank, which had a cozy relationship with prominent liberal politicians, including a controversial unsecured loan to Congressman Dick Gephardt’s 1988 presidential campaign. The bank was cited by federal bank examiners for “unsafe and unsound banking practices” which led to a regulator crackdown and its eventual sale.
Some argue that the worst example of McAuliffe’s politically-driven business career is his role as a consultant to Global Crossing CEO Gary Winnick. McAuliffe made a $100,000 investment in the company while setting up golf games between President Bill Clinton and Winnick. Yet, Global Crossing was on the path to failure. The company filed for bankruptcy, 10,000 workers lost their jobs, and billions in pensions and retirement savings evaporated. McAuliffe, labeled a “Winnick crony,” however, managed to make a handsome $8 million windfall off of his $100,000 investment. Meanwhile, Global Crossing’s bankruptcy would be compared to the debacle of energy giant Enron, and Winnick and Global Crossing would be the subject of FBI and SEC investigations.