How Bloomberg won his first race as a billionaire underdog
By the late 1990s, financially megasecure and professionally restless, the billionaire businessman had told friends that four jobs on earth could tempt him away from his company: president of the United States, secretary-general of the United Nations, president of the World Bank and mayor of New York.
He entered the race in June, three months before the Republican primary, appearing so stiff at an introductory news conference that a reporter had to instruct him on how to proceed. “That’s not going to stop, no matter what I do?” Bloomberg asked anxiously as cameras clicked.Nearly two decades later, as Bloomberg plots an unconventional path to the Democratic presidential nomination, allies see his first mayoral run as proof of concept.
In a flash, the October endorsement from Giuliani, the lame-duck leader suddenly elevated to temporary political deity, also became the highest of municipal blessings. In public, he would broadcast ads trumpeting the more than $100 million he donated to various philanthropies the year before, including Gay Men’s Health Crisis and the Committee to Protect Journalists.
Quickly, some uncomfortable alliances were deemed necessary. Bloomberg, who had determined he could not survive a crowded Democratic primary, won the backing of many Republican officials with the promise of self-funding, despite his socially liberal views. Three of his employees and the brother of a campaign aide were missing. The primary was postponed — all political activity was suspended — but no one much worried about that. Bloomberg had donated one of his company’s spaces downtown for emergency workers seeking food.
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