Late last year, Rudy Giuliani was sitting in the library at Gracie Mansion, offering career advice to a visitor--billionaire media mogul Michael Bloomberg. The financial-data tycoon was thinking about changing jobs. Among the possibilities he'd been mulling: President of the United States, Secretary-General of the United Nations and--his top choice--mayor of New York City, and never mind that he had no experience in government. Giuliani could see he was serious about the third idea. A lifelong Democrat, Bloomberg intended to switch parties in order to have a clear shot at the Republican nomination. Giuliani, who has known Bloomberg for years, understood he had the resources to run and figured he'd be a moderate. He promised his support, the mayor told TIME, but he didn't think Bloomberg had much of a chance. "In New York we only elect Republicans when we're in real trouble," Giuliani says. "So, in a way, my administration had not created the mood to help Republicans win." By September, Bloomberg had spent more than $20 million on his campaign, but not even his own supporters expected him to win.
Then the Twin Towers blew up on the morning of the Democratic primary. The election was postponed, Giuliani's stature soared as he helped the city crawl from the wreckage, and when the general election was finally held last week, the whole country was paying attention. The billionaire who didn't have a chance squeezed out a victory anyway--defeating city public advocate Mark Green by about 40,000 votes out of a total 1.4 million cast--and he did so largely because of Giuliani's dramatic endorsement.
On Oct. 29, just eight days before Election Day, Bloomberg's media team--legendary New York consultant David Garth and Bill Knapp, a Washington-based consultant who worked for Bill Clinton and Al Gore--released a commercial that turned Giuliani's support into electoral gold. A fatherly endorsement of Bloomberg and a warm farewell to his city, Rudy's words would echo on TV and radio like a lullaby for the next week. "You may not have always agreed with me," he said, "but I gave it my all. I love this city, and I'm confident it will be in good hands with Mike Bloomberg." During the World Series, says Mickey Carroll of the Quinnipiac Polling Institute, "it was as if Giuliani were campaigning in your living room. You practically had to look over his shoulder to see the game."
In exit polls by Edison Media Research, a quarter of those surveyed said Rudy's recommendation had influenced them to back Bloomberg. Voters who had made up their minds in the last week went 3 to 2 for Bloomberg. They were looking for guidance about who should lead them through perilous times--with downtown still smoldering, the largest budget deficits in city history looming and some 100,000 people unemployed as a result of the attack--and there seemed no better counselor than the man who'd been leading them so well. A city where Democrats outnumber Republicans 5 to 1 put back-to-back Republicans in office for the first time ever. In effect, this was Giuliani's third successful election, the one he had longed for but was barred by term limits from joining. "I didn't recognize how powerful the endorsement would be," he told TIME. "I'd become a different figure."