Instead of politics or law, Kennedy ventured into publishing, founding George, a political-culture magazine, in 1995. Kennedy was editor-in-chief of George until his death. George ceased publication in early 2001.

Kennedy also pursued philanthropy, serving on the boards of several foundations and a number of nonprofit organizations.

An avid athlete, People named Kennedy the "Sexiest Man Alive" in 1988.

Kennedy unveiled the "inaugural" issue of George in 1995.