Giuliani's Policy Professor

The elder Simon came away from the experience of Watergate with a disgust for the partisan character of the affair, and the capital. The experience of impeachment convinced him, like members of the liberal "Net roots" 30 years later, not that partisanship was necessarily poisonous, but that his opponents were far better at partisanship than his side was.

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The experience "had a very combative influence on Bill Simon the father," said James Piereson, president of the William E. Simon Foundation. Simon would spend the remainder of his life helping to redress the balance -- spending years on the boards of the Heritage and Olin foundations and the Hoover Institution -- in his person melding the old Republican establishment with the antsy, rising conservative one.

For all the aggression of his father's parenting style, Bill Simon Jr. followed him in his politics ("basically a chip off the old block in terms of his perspective," Feulner says); his deeply felt, conservative Catholicism (a Knight of Malta, Simon makes a pilgrimage to the cathedral in Lourdes, France, every year); and ultimately, his career.

After Williams College and law school at Boston College, Simon went to work for Giuliani, then the U.S. attorney in New York. Simon said he saw an innovative public policy sensibility in his old boss: "Rudy pioneered investigations in the forfeiture area, the use of criminal RICO [racketeering law], areas of law that hadn't previously been explored."

By the late 1990s, Simon had moved to Los Angeles and was running his family's investment firm with his brother and father and serving on the boards of conservative groups: Heritage, Hoover and his father's foundation. He struck associates as less of an ideologue than his father, a quick study but not a committed policy man.

In 2000, three months after his father died, Simon decided to run for governor after being approached by some members of the California Republican organization. Simon ran as the conservative in the Republican primary in 2002, attacking Democratic Gov. Gray Davis over the looming budget deficit, and used his experience at Hoover and Heritage to frame himself as the candidate of ideas needed to fix a failing state.

Simon cast himself as an insurgent conservative candidate, and he upset the favorite in the primary, former Los Angeles mayor Richard Riordan, a moderate. Later, as it became clear that a Davis victory in the general election was likely, Simon's media consultant, Ed Rollins, developed a very aggressive, last-ditch, anti-immigration television ad that he wanted the campaign to run. Opinion in the campaign was divided; many thought it simply nasty, politics at its worst, while others considered it Simon's last, best chance.

Simon decided not to run the ad, and he lost by five percentage points.

'Proud to Be His Friend'

During presidential campaigns, relationships can come encased in legend. For Simon, the source of his legend is that he happened to be in New York on the morning of Sept. 11, 2001, and happened to be eating breakfast with the mayor when the World Trade Center was struck.

They were discussing Simon's gubernatorial bid and preparing to leave when Giuliani got the call and rushed downtown. Simon watched the next days unfold and saw Giuliani acquire the aura that has been a sustaining basis of his presidential candidacy. "When I watched Rudy on TV, I wouldn't say I was surprised about how he reacted," Simon recalls, "but I will say I was proud to be his friend."

Over the summer of 2006, as Giuliani began to seriously contemplate a presidential run, Simon began hosting occasional roundtables with scholars at Stanford University's Hoover Institution during the former mayor's California trips. He eventually signed on as the policy director for his friend's presidential campaign.