So if he doesn’t run, what exactly is all this flirting about? Part of the answer is that Rudy Giuliani is more than a politician. He is also a businessman.
One of the most spectacular failures in presidential-primary history concluded on January 30, 2008. That was the day Rudy Giuliani, fresh from his 15 percent, third-place showing in the Florida Republican primary, appeared next to John McCain and announced he was dropping out and endorsing his former rival as the best man for the job. “Obviously, I thought I was that person,” Rudy said at the time. “The voters made another choice.”
No one—not John McCain, not Bill Clinton—walked away from the 2008 presidential campaign as diminished as Rudy Giuliani. He entered the campaign with one of the most valuable brands in American politics and drove it straight into a tree. It’s hard to chronicle all the embarrassments: the Kerik indictment, the stories about taxpayer funds spent for his then-girlfriend Judith Nathan’s security; that bizarre cell-phone call he took from Nathan during a 2007 speech to the NRA.
And then there was his cockamamy campaign strategy, in which he sat out the Iowa caucuses, skipping a contest that riveted the world for a month, and competed halfheartedly in New Hampshire and South Carolina. By the time he made his infamous last stand in Florida, hoping that weeks of appearances at NASCAR tracks and Little Havana parades could make up for the ground he’d lost, it was too late.
Today, Rudy Inc. offers myriad excuses for the debacle. Giuliani says fund-raising in the crowded field was harder than he expected: “I wish I had figured out that we weren’t going to raise $100 million.” Giuliani also wishes he hadn’t skipped Iowa, a decision he attributes to advisers. “My instincts originally were, if you lose, you gotta go down fighting. You can’t allow yourself to lose a primary. I think I should’ve fought Iowa harder. That was the beginning of becoming irrelevant.”
But the irrelevance was only part of the problem. Well aware that a pro-choice, thrice-married, and occasionally cross-dressing New Yorker would be hard-pressed to win over the social conservatives who control the Republican nomination process, Rudy changed his spots, putting a dark and often sneering emphasis on national security. He charged that Democrats “do not understand the full nature and scope of the terrorist war against us” and warned that America would suffer “more losses” under their approach. (Obama called this “taking the politics of fear to a new low.”) His top campaign allies included Sean Hannity and Pat Robertson, the latter of whom endorsed Rudy on the grounds that he best understood “the defense of our population against the bloodlust of Islamic terrorists.” And later there was his memorably taunting speech at the Republican convention, in which he ridiculed Obama’s experience—“Barack Obama has never led anything. Nothing. Nada”—and literally laughed out loud when he uttered the words “community organizer.” And his relentless focus on the aftermath of the World Trade Center attack allowed him to become a self-parody, captured memorably by Joe Biden: “There’s only three things he mentions in a sentence—a noun and a verb, and 9/11.”
In May 2008, three months after leaving the presidential race, Giuliani appeared at a Times Square press conference with an unlikely partner: one Vitali Klitschko, a Ukrainian boxer known as “Dr. Iron Fist” for his Ph.D. in sports science. In addition to smashing men in the jaw, Dr. Klitschko dabbles in politics and was running for mayor of the Ukrainian capital, Kiev. Giuliani, who says he has made many friends in Eastern Europe through his business ventures, recalls that Klitschko approached him to “figure out an anti-corruption program for Kiev” (which Rudy pronounced Keev). “Reform is possible if you have the right candidate and the right set of ideas,” Giuliani declared at the press conference, the buff fighter looming over him in a dark suit. “Kiev can accomplish this.” But Klitschko wound up suffering a TKO at the ballot box, and today Rudy dismisses the work as “a really short assignment”—although he still predicts that Klitschko, who last month successfully defended his world heavyweight title, “will eventually be, God willing, the president of the Ukraine.”
Klitschko was not exactly an A-list client. And the episode suggested that after his national flameout, Rudy wasn’t in a position to be highly selective about where he took work. After quitting the campaign, Giuliani returned to his business ventures. But finishing behind Ron Paul and Fred Thompson in several states will put a dent in a man’s business brand. Giuliani’s speaking fees reportedly sagged as much as $25,000 from a peak of $100,000. More significant was the impact on Giuliani Partners, the business he founded weeks after leaving City Hall.