From 2001 to 2004, Craig served as Ambassador to the Czech Republic. He was awarded the Jan Masaryk Medal for service to the Czech Republic. In 2004, Craig acted as Connecticut State Chairman for the re-election campaign of President Bush. From 1982 to 2001, he was the President of Marsh and McLennan Real Estate Advisors of New York. Under President George H. W. Bush, Craig served on the Board of the Peace Corps. In 2000, he became the Connecticut State Finance chairman of the Bush-Cheney Presidential Campaign. From 1989 to 1998, Craig joined President Bush in the ownership of the Texas Rangers baseball team. He has been a member on the Visiting Committee for Harvard College and the Committee on University Resources and Athletics. Craig received a B.A. (magna cum laude) from Harvard University and his M.B.A. from Harvard Business School. He resides with his wife, Dorothy Walker Stapleton, in Greenwich, Connecticut. The Stapletons have two children and five grandchildren.