I stand by my one question licensing quiz for political pundits:
"Is today the right moment to get excited about a third-party presidential run?" If you answer "yes," you need to find some other line of work.
That said, people do mount independent campaigns, and though they never win, they do influence political outcomes. Thus, the prospect of a Bloomberg bid is worth discussing.
To me, it seems to be all about the matchups. Against Barack Obama's length and "fresh face" appeal, there's little rationale for a Bloomberg bid. Similarly, John McCain's "maverick" branding and Rudy Giuliani's somewhat similar political profile make this hard to pull off. On the GOP side, though, Mitt Romney and (especially) Fred Thompson are positioning themselves as the candidates of tired, old-school conservatism thus creating an opening. On the Democratic side, it's obvious that the best nominee to run against as a third party is Hillary Clinton, who has by the least appeal outside the party's base.
Unfortunately for Bloomberg, the potential Democratic voters likely to be unenthusiastic about Clinton -- working class white men, primarily -- aren't a great constituency for a culturally liberal Jewish mayor of New York City, either. That leaves Bloomberg hoping for a Fred Thompson versus John Edwards matchup in which he tries to get voters in the top-right corner of the Nolan Chart. A campaign like that -- balanced budgets, free trade, vaguely progressive on cultural issues, entitlement reform, mildly environmentalist, progressive on some small-bore economic topics -- is ideally positioned to get a ton of positive coverage from the elite press (and elites generally) plus maybe even 10-15 percent of the electorate depending on how much cash Bloomberg's willing to spend and how effective he is as a campaigner.
Photo by Flickr user ceonyc used under a Creative Commons license
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