Easy, Kev
Just hours after New York City Mayor (and AIS hero) Mike Bloomberg made his definitive announcement that he wouldn't be seeking the presidency as an independent candidate in 2008, top Bloomberg political aide Kevin Sheekey put the mayor's political plans and ambitions back in the news with public speculation that Bloomberg could be a strong running mate for Barack Obama. Sheekey says, "I think the mayor is the ultimate swing voter. He is someone who the country is looking at to find out where they will go. He is one of the true independents in the country.”

I guess that in some sense, anyone with a net work of $12 billion or so who hasn't publicly committed to supporting any candidate could be fairly described as "the ultimate swing voter." And some already have tried to parse Bloomberg's Times op-ed for clues as to who he might ultimately endorse. Michael Tomasky, who's usually pretty smart, screws up this exercise IMO by giving all his considerations--free trade, immigration reform, education reform and global warming--equal weight, while leaving out altogether the most important substance graf in Bloomberg's piece:

In every city I have visited — from Baltimore to New Orleans to Seattle — the message of an independent approach has resonated strongly, and so has the need for a new urban agenda. More than 65 percent of Americans now live in urban areas — our nation’s economic engines. But you would never know that listening to the presidential candidates. At a time when our national economy is sputtering, to say the least, what are we doing to fuel job growth in our cities, and to revive cities that have never fully recovered from the manufacturing losses of recent decades?

So let's see: you've got John McCain, a member of Congress for a quarter-century whose signature issue at this point is foreign policy, and whose past admirable steps toward political process reform (which indirectly benefits cities by weakening the power of special interests to divert public resources for everything else) he's now mostly trying to push under the rug in hopes of winning over right-wingers. Then you've got Barack Obama, whose formative political experiences were as a community organizer in an impoverished section of Chicago and a state senator representing a wealthier part of Chicago. Seems one of the two is more attuned toward the concerns and hopes of those championing an urban agenda than others, no?

(And yes, I know Hillary Clinton is still in the race, and that in some sense she represents New York City. But while their relationship is said to be cordial, I find it unimaginable that Bloomberg would support the woman who embodies the Democratic political establishment, if not the Beltway mindset itself. Perhaps more to the point, Hillary leadership on urban issues other than trying to get more Homeland Security funding for NYC has been non-existent.)

Still, I'd be pretty comfortable betting money I don't really have that Bloomberg won't be Obama's running mate. The reasons why are both political and stylistic: if Bloomberg, a big-time social liberal whom even his admirers (like me) readily concede doesn't exactly have the Common Touch, really can appeal to swing voters and independents, I haven't seen it. What states, other than perhaps Florida (which would be a big deal if proven), could he swing for Obama? And what would be his policy portfolio within an Obama administration? Much as it might cause me to drop dead in bliss to hear Bloomberg named as an urban policy tsar, it's not gonna happen--and even if it did, I'm not sure it would tilt cities all that much more into the Democratic camp than they already are. That leaves his money, and while Obama might or might not ultimately agree to accept public financing for the general election, even if he didn't I doubt the inevitable accusation that the billionaire plutocrat running mate (I could add "Jew" in there) was funding his run would sit well with the outsider, reformist mantle he wants to claim.

Maybe an even bigger issue is that I doubt Bloomberg has been anyone's Number Two in thirty years if not more. As a CEO and as a mayor, he's known as an almost archetypical enlightened despot: smart, communicative, extremely supportive of his deputies--but absolutely the man. At this point, he simply couldn't play second fiddle. Perhaps for a president as insecure in his abilities and uninterested in detail as George W. Bush, Bloomberg could play the non-evil Cheney role. But that's not Barack Obama, thank goodness.

Ultimately it wouldn't shock me if Bloomberg did endorse Obama and even agreed to serve in some role, formal or otherwise, in an Obama administration. (It's easier for me to see Bloomberg as Treasury Secretary, or even Education Secretary, than VP; in a federal cabinet agency, enlightened despotism kind of works, and you can be semi-autonomous.) I think he likes McCain, but realizes that the septuagenarian Senator is too tied to a party that fundamentally opposes everything Bloomberg stands for. And the mayor's mix of liberal ends with pragmatic and market-oriented means matches up very well with Obama's own public persona. But he would add a lot more at arm's length than in the full and somewhat involuntary embrace that second standing on the ticket requires.