The Revolutionary

The electoral war-gaming can quickly turn into political porn: Whom would Bloomberg hurt most? Could he craft a centrist message—he is a Democrat turned Republican turned independent—and spend so much promoting it in major media markets that he could take a plurality of the popular vote? If he did that, but failed to win the necessary 270 votes in the Electoral College, what would happen? Under the Constitution, the college's failure to elect sends the presidential decision to the House of Representatives, where Democrats hold a majority. (The Congress that is elected in November 2008 would render the verdict.) In that scenario, assuming the Democrats hold on to the House, the Democratic nominee, whoever he or she may be, is the most likely winner.

The clearest-cut alternative is an outright Electoral College victory built on carrying California, New York, Texas—or, in Sheekey's musings, a Congress that decides the 18th-century system of checks and balances should not dictate the selection of a president who did not receive the most votes. "When we went through Florida in 2000, there was a great uneasiness about choosing the guy who may not have gotten the most popular votes," Sheekey says. "Would a Democratic Congress really want to reach down and pick a second- or even third-place candidate to install as president if Bloomberg were to win the most votes? I think that is an open question."

What is not open to question is Bloomberg's steadiness, self-confidence and apparent sanity (the last not being the most common of political traits). "I've been very lucky," Bloomberg says. "My parents gave me a Norman Rockwell kind of upbringing; my father worked seven days a week until he checked himself into the hospital to die; my academic record was never stellar, but it wasn't a disaster, either. I am a believer in what I learned in seventh-grade civics: I really down inside believe that everybody in this country has an opportunity … America is built around this premise that you can do it, and there are an awful lot of people who are unlikely to have done it who did."

His mother, now 98 and still living in the family house, appears never to have doubted that her son could do whatever he wanted. Young Michael, says Charlotte Bloomberg, was always "self-sufficient," always confident. His closest friend in the neighborhood was a boy two years his elder, and he ran with a crowd of older boys. "He could get along with boys that were older than he, he had enough self-confidence," she says. Public speaking came especially naturally to him. As an elementary-school student at the Gleason School, Bloomberg would take part every year in a Memorial Day ceremony. Each year, one student would be picked to give a speech. "You just knew ahead of time that he was going to be the one," Bloomberg's mother says. "It never seemed to bother him to get out in front of an audience and talk."

Bloomberg's academic adventures were not always as heroic as his mother remembers now. He could be an uneven student, though his dustups say more about his character than his mind. "He has a towering intellect," says his sister, Marjorie Bloom-berg Tiven. "In high school, did he use it all the time? No, but he used it on things he was interested in, and he did things the way he wanted. I remember the year he took two math courses, getting an A in one and a D in the other. My parents were baffled, and it turned out that in the course where he got the D he had written down all the correct answers on the final, but he had done the work in his head, and did not show how he had gotten them, so the teacher assumed he was cheating."

Bloomberg recalls a similar story from Harvard Business School. "Yeah, I've had a stubborn streak. In graduate school, you were supposed to write 10 pages solving a problem, and I wrote half a page saying there really wasn't a problem because one of the facts was wrong. After the second time I did that, I got called in and it was explained to me that if I wanted to graduate, then I'd stick to the rules, look at what they're trying to do, and don't be a cute wise guy."