Boies attended University of Redlands and law school at Northwestern and Yale. He received a B.S. from Northwestern in 1964, an LL.B. magna cum laude from Yale in 1966, am LL.M. from New York University 1967, and an LL.D. from the University of Redlands in 2000.
He helped defend IBM in an antitrust case, and years later famously took the other side by representing the Justice Department in the Microsoft antitrust case. Following the 2000 U.S. presidential election, he represented Vice President Al Gore in the ensuing legal battle and participated in Bush v. Gore, one of the few Supreme Court cases ever televised. He has also, unsuccessfully, defended Napster when the company was sued by the RIAA for facilitating copyright infringement.
As of November 2003, he is representing deposed Chief Financial Officer of Enron Andrew Fastow, and has been retained by the SCO Group in their pursuit of alleged infringement of their rights to the UNIX intellectual properties. He is also representing Conrad Black regarding the U.S. Securities and Exchange Commission and the Ontario Securities Commission probes of Hollinger International's disclosure of $32 million (U.S.) in unauthorized payments to Black, fellow executives, and parent Hollinger Inc
Other clients of his had during his career include Tyco International Ltd, Qwest Communications International Inc, and Adelphia Communications Corp.
Boies was also Chief Counsel and Staff Director of the United States Senate Antitrust Subcommittee in 1978. He also served as Chief Counsel and Staff Director of the United States Senate Judiciary Committee in 1979.