Word: bloomberg
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Dates: during 2000-2009
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...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...
...Clearly Bloomberg does not plan to enter the race until he sees whom the major parties settle on as nominees, likely early next year. At that point, he would look to see how unfavorably those two candidates are seen, how sour the mood of the country is on politics-as-usual, and how open the electorate seems to a candidate Bloomberg himself describes as "a short, Jewish, divorced billionaire," one who has now turned his back on both the Democrats and the Republicans...
...here's the thing: Bloomberg will only enter the race if he believes he has a reasonable chance to win, but he almost certainly never will be the favorite to win, simply because as an independent he could not be expected to get more than, say, 35% of the vote at best, requiring the political equivalent of drawing an inside straight to win the necessary 270 electoral votes to take the White House. Even H. Ross Perot, despite taking a respectable 19% of the popular vote in 1992, couldn't win a single electoral vote...
...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...
...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...