David BoiesS

One of the most prominent trial attorneys in America, Boies is best known for unsuccessfully representing Al Gore during the legal wrangling after the 2000 presidential election and for teaming up with Bush v. Gore adversary Theodore Olsen for challenging the constitutionality of Prop 8.

Boies attended the University of Redlands before deciding to enroll in the law program at Northwestern. When he was caught having an affair with the wife of a professor, he was banished from campus, and headed to Yale to finish his law degree. (Boies eventually married the woman.) He joined powerhouse firm Cravath Swaine shortly afterward and steadily climbed the ranks, gaining prominence for his work during the high-profile (and protracted) IBM antitrust suit, which carried on for more than a decade. In the early '90s he made headlines representing the FDIC in insider trading litigation, a case that ended with junk bond king Michael Milken paying a $1.1 billion settlement. One of Boies's most enduring clients has been the New York Yankees, but his firm was counsel to Time Warner and when the media giant acquired Turner Broadcasting in the mid-1990s, it inherited ownership of the Atlanta Braves. To avoid a conflict of interest, Boies was told to drop the Yankees as a client. He quit instead and co-founded Boies, Schiller & Flexner in 1997. Not long after, he landed back in the spotlight when he helped the U.S. government win its 1998 antitrust suit against Microsoft.

Boies took on Al Gore's case in 2000 pro bono, and represented Gore all the way up to the Supreme Court, where he lost in a history-making 5-4 decision. For a number of years, Boies largely stayed out of the political spotlight and focused on building his private practice, including Ken Chenault at American Express who hired him in an antitrust action against Visa and Mastercard. But he entered the political fray again in 2009 when the American Foundation for Equal Rights sought to overturn the ban on gay marriage, Proposition 8, which was found unconstitutional. [Image via Getty]