National Review,
December 17, 2007

As Bill Simon Jr. prepared to run for governor of California, he sought the advice of his old boss, Rudy Giuliani. They agreed to have breakfast at The Peninsula, a ritzy hotel in Manhattan. The date was September 11, 2001.

About 45 minutes into their meal, a member of Giuliani’s detail handed the mayor a cellphone. “There was a brief conversation,” recalls Simon. When it was over, Giuliani said that there had been some kind of incident involving a plane at the World Trade Center. “I’ve got to go,” he said.

Giuliani went on to become “America’s mayor,” Time’s “Person of the Year,” and all the rest. Simon captured his state’s GOP nomination but lost the general election in 2002. Now these two have teamed up again, only this time Giuliani is seeking Simon’s help. As policy director of the Giuliani presidential campaign, Simon is the head of what might be called Giuliani’s brain trust — a network of more than 150 policy experts who counsel the Republican frontrunner on everything from North Korea to health care. The ranks of a Giuliani administration would draw heavily from this crowd, and Simon himself could be in line for a big job.

For the 56-year-old Simon, it might mean following in the footsteps of his father, William E. Simon, who was secretary of the treasury under Presidents Nixon and Ford. The senior Simon was known not only for his horn-rimmed glasses but also for a hard-charging conservatism that blended his famously short temper with a deep commitment to free-market principles. After leaving government, he served as president of the John M. Olin Foundation, a right-leaning philanthropy, until his death in 2000.

Around the time the Olin Foundation was turning into a major underwriter of the conservative intelligentsia, Simon’s oldest son — “Billy” to intimates — was graduating from Boston College Law School. A couple of years later, he became a federal prosecutor under Giuliani, who was then U.S. attorney for the Southern District of New York. “Some accounts make it sound like I was his right-hand man,” says Simon. “But I was a rookie assistant.” Between 1985 and 1988, Simon and Giuliani nevertheless got to know each other. They stayed in touch even after Simon left to become his father’s business partner and Giuliani pursued a political career.

Last year, when it became obvious that Giuliani was thinking about the White House, Simon offered to help. “I knew his campaign would need a policy infrastructure,” he says. “I asked him what I could do.” Before long, Simon arranged for Giuliani to meet with Hoover Institution scholars at the Pacific Union Club in San Francisco on August 18, 2006. Attendees included Hoover director John Raisian, economics guru Michael Boskin, and the late Milton Friedman. “Everyone thought Giuliani was smart and quick,” says Martin Anderson, who was there. He signed on with the campaign, as did several other Hooverites, including Boskin, who is now its chief economics adviser.

As summer turned to fall, Simon drafted memos to Giuliani and asked James Piereson, the longtime executive director of the Olin Foundation, to lend a hand. Giuliani encouraged them to work with John Avlon, who was chief speechwriter for the mayor during his second term. They were soon joined by Stephen Goldsmith, the former Republican mayor of Indianapolis who had advised President Bush on domestic policy during the 2000 race. In Giuliani’s circle, this group was nicknamed the Four Horsemen. “You’d think there’s a more elite-sounding phrase for us,” laughs Goldsmith. Yet nobody calls them the Quartet of Wonkdom.

Their immediate priority was to schedule briefings. Giuliani wanted the first set to focus on Iraq, and so they did, during the first week of January 2007. “He asked for a variety of perspectives and that’s what we gave him,” says Simon. “From a center-right viewpoint, we included both supporters and critics of the president’s strategy.” Neoconservative hawk Norman Podhoretz met with Giuliani in person. Republican war skeptic Richard Haass of the Council on Foreign Relations paid his own visit. Retired Marine general Anthony Zinni, who opposed the invasion, participated on speakerphone. American Enterprise Institute scholar Frederick Kagan and former Army general Jack Keane argued for the troop surge.

This wasn’t the first time Giuliani had reached out to policy intellectuals. During the 1990s, he developed a close relationship with the Manhattan Institute, a free-market outfit. Between Giuliani’s mayoral defeat in 1989 and his first victory in 1993, he began reading the institute’s City Journal and took notes at a conference on urban issues. Major themes in both venues included welfare reform and the “broken windows” theory of crime control. As mayor, Giuliani became a champion of both. “He borrowed a lot of our ideas,” says Larry Mone, president of the Manhattan Institute. On June 21, 1999, the mayor declared it “Manhattan Institute for Policy Research Day” in New York City.

Since the Iraq briefings, Giuliani has attended sessions on subjects ranging from energy to taxes. Along the way, he has assembled a crew of conservative and libertarian advisers: Clint Bolick on education, Louis Freeh on homeland security, Charles Hill on foreign policy, Ted Olson on judges, and Sally Pipes on health care. “We’re like a mini-think tank,” says Simon. The campaign also has sought advice from experts who haven’t publicly endorsed Giuliani. “I’ve spoken with him and helped organize some briefings,” says former U.N. ambassador John Bolton, now of AEI. “It was a pleasure to do it for him, but we would do it for any presidential candidate, including Hillary if she ever asked.”

Giuliani’s political vision is spelled out most concisely in the “12 Commitments,” a package of promises on how he would govern. The Four Horsemen look for opportunities for Giuliani to put flesh on the bones of this campaign centerpiece. Foreign Affairs recently carried a 6,000-word article by Giuliani — a summary of how he views the world. “He knows his own mind and has a clear vision,” says Simon. “We help fill in some details and provide some facts.” An idea in one area can affect another, and so the campaign’s policy machinery churns nonstop. In May, at a speech at the Citadel, Giuliani proposed adding ten new combat brigades to the Army — but not before his economics advisers had calculated the cost. “We have to figure out what it means for our budget and tax plans,” says Piereson. “If we don’t, our opponents will.”

One of the pledges in the 12 Commitments involves abortion. It speaks of “reasonable restrictions” — but, conspicuously for a GOP candidate, it isn’t a pro-life plank. “He’s pro-choice,” says Simon, who is himself a pro-life Catholic. Does it discomfort Simon to work for a man who supports abortion rights? The question bothers him. “My faith is very important to me and I believe the mayor is a man of faith,” he says, in carefully measured words. “Even within the abortion context we agree on partial-birth abortion, parental notification, and judges.”

If Giuliani is ever to gain even grudging support from pro-lifers, he’ll have to do it through judges. Many pro-lifers understand that the next two or three Supreme Court appointees may determine the future of Roe v. Wade, either to cement its place in American jurisprudence or to weaken it fatally. At a speech on November 16 at the national convention of the Federalist Society, Giuliani courted some of conservatism’s finest legal minds. He promised to nominate justices similar to John Roberts, Samuel Alito, Antonin Scalia, and Clarence Thomas. “That would be my model,” he said. The pro-life case for a pro-choice candidate then becomes a prudential one: Better to win with Giuliani and this commitment on judges than to lose with Mitt Romney or someone else.

These are high-flying judicial and political questions, but the Giuliani policy team also participates in the daily give-and-take of a grinding campaign. At the Republican presidential debate on October 9, Romney attacked Giuliani for going to court over the line-item veto in 1997. Right away, Giuliani’s campaign put out a statement from Olson, defending his man. The dispute spilled into the next day, with Romney adviser Douglas Kmiec, a Pepperdine law professor, attacking Giuliani in piece for National Review Online. Within hours, Steven Calabresi, a Northwestern law professor from the Giuliani camp, posted a rebuttal. “We have policy people standing by, ready to respond to anything at a moment’s notice,” says Avlon.

The wide-open GOP nomination probably won’t hinge on decade-old disputes about the line-item veto. Yet it may come down to some other piece of policy minutiae. If that happens, the result will flow from the statements and positions of the candidates themselves. And these, of course, will have been influenced and shaped by experts like the ones Bill Simon Jr. has recruited for Rudy Giuliani.