In 2002, Simon campaigned unsuccessfully for Governor of California as a Republican against Democratic incumbent Gray Davis.

[1] Simon managed the family business (which has over $3 billion in assets), as the Assistant U.S. Attorney for the Southern District of New York, and as a trustee for The Heritage Foundation.

[1] Simon has contributed some of his personal resources to assist less fortunate youths through educational scholarships and beautification of California schools.

Some credit Simon's primary win to incumbent Governor Gray Davis' preemptive campaign against Simon's major primary opponent, former Los Angeles mayor Richard Riordan, a moderate Republican, whom Davis considered a more formidable opponent.

Simon's come-from-behind win reflected both the GOP's dissatisfaction with Riordan's inability to appeal to the GOP base (he had publicly insulted George Deukmejian, California's most popular Republican governor since Ronald Reagan, and it was revealed that he had supported Democratic Senator Dianne Feinstein with campaign contributions) and support for Simon's straight-conservative image.

Simon's campaign centered largely on allegations of corruption in the incumbent's administration, and Davis's handling of the 2001 energy crisis.

Simon spent most of 2004 and 2005 preparing to run for California state treasurer in 2006, and although he was the clear front-runner for the Republican nomination, he dropped out in October 2005 citing the need to devote more time and attention to his family and four children.

They live in Pacific Palisades, Los Angeles, and have a vacation home on Maui and one in Sun Valley, Idaho.