The Southern California Republican's most recent foray into politics was as state chair of his former boss Rudy Giuliani's failed presidential run. He shares the experience of backing losers with Whitman, who supported Mitt Romney in last year's presidential campaign before switching her support to John McCain.
The socially conservative Simon won the Republican nomination for governor in 2002, but lost to Democrat Gray Davis -- even after Davis presided over the disastrous energy crisis in the summer of 2001, but before Davis was recalled and replaced by current Governor Arnold Schwarzenegger.
Like Whitman, Simon has dithered on issues of rights for same-sex couples.
In 2002, Simon endorsed much of the Log Cabin Republican platform including civil unions and adoptions for same-sex couples before saying that he'd never read the group's questionnaire.
Luckily for Whitman, she does have some winners on her side -- former Governor Pete Wilson serves as the chair of the Whitman for Governor 2010 Exploratory Committee.
Simon will serve as co-chair of the committee, as well as senior policy advisor.
Jackson West certainly thinks this will help Whitman with social conservatives, though it may hurt her chances to garner donations from wealthy, centrist Republicans.