New York Mayor Michael Bloomberg
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So the more urgent question is, which party would be more hurt by his entry into the race?
Although there are statistics and arguments on both sides, Perot almost certainly hurt George H.W. Bush and Bob Dole (and helped Bill Clinton) in his two Presidential runs, while Ralph Nader clearly benefited George W. Bush in 2000 against Al Gore. Despite Bloomberg's reformist views on welfare and education that put him more in line with conservatives, on a national level, he would almost certainly hurt the Democratic nominee more than the Republican.
But Presidential elections aren't national contests — they are races to those 270 electoral votes. Playing around with the National Archives Electoral College calculator (as I did for most of my morning Wednesday) shows that it isn't impossible for Bloomberg to get enough votes to win, but it is tough indeed. The more interesting question is which reliably Red and Blue states could shift from one side to the other with Bloomberg on the ballot. Of course, determining that in a rigorous way is impossible without knowing who the other candidates will be among the various possible combinations (the all-New York match up of Giuliani versus Clinton versus Bloomberg is particularly imponderable), and without knowing what the mood of the nation will be in 2008.
It appears that a massively funded Bloomberg candidacy would endanger more states won by Gore and Kerry than those won by Bush. On the other hand, if Bloomberg was able to pick off some electoral votes, he could theoretically throw the outcome into the House of Representatives, producing another set of complex what-ifs.
We won't know until next year if Bloomberg will run. And unlike political reporters, who have the time and inclination to speculate endlessly about every possible eventuality, presidential campaigns live by one simple rule: don't worry about things you can't control. For now, all of the announced Presidential candidates are locked in fierce trench warfare trying to secure their positions on the general election ballot as their party's nominee. Wondering how to beat Michael Bloomberg will wait for another day, down the road and a million political years away.