Freeman was introduced to George W. Bush in 1979, and the two quickly became good friends.[1] Freeman served on the "Team of 100," George H. W. Bush's group of top fundraisers, and helped raise funds for George W. Bush's campaigns for Governor of Texas.[2] Freeman served as a "Pioneer" in Bush's 2000 presidential campaign and helped raise millions of dollars for Bush and the Republican National Committee.[1] Freeman also served as chairman of the 2000 Presidential Inaugural Committee.[1] Though Freeman himself did not earn a major presidential appointment,[2] Freeman's business partner, Ron Spogli, was appointed Ambassador to Italy in 2005.[4]
In the 2016 film Meet the Donors: Does Money Talk, Freeman said that after raising and contributing millions of dollars to George W. Bush's 2000 presidential campaign, he was expecting a government appointment such as "a chance to run the CIA," but Bush instead offered him his cat.[5] According to friends, Bush did arrange for Freeman a membership of Augusta National Golf Club.
Freeman has served on the board of trustees of Stanford University.[3]