Can Bloomberg Actually Win?

Yes, I know the obvious answer is, "No". And it's probably the right answer. 

But over at Politico, David Freedlander has an elaborate layout of what I've been saying, which is that Bloomberg was a terrible candidate who won, not just because he spend a lot of money, but spent it tactically on buying up every faction and special interest in the city.

In addition to wooing the Republican mayor, Bloomberg made another adroit move to assure wary Republicans of his devotion to his new party: He donated money to the five county Republican parties in New York City. The amounts were not huge, but for county parties no one much paid attention to, they were enough to bring loyalty...

New York’s unique voting laws meant Bloomberg didn’t just run as a Republican, he also sought the Independence Party line. The group was controversial: Among its leaders were Lenora Fulani, an activist who had made a series of inflammatory remarks, including that “Jews are mass murderers of people of color,” and Fred Newman, a psychotherapist who has been accused of operating a “therapy cult” that encouraged sex among therapists and patients... He gave the party $250,000, and the day after he announced, he was officially a candidate 

Bloomberg got 59,000 votes on the Independence line, largely if not primarily from Democrats and liberals who blanched voting Republican. He won the race by fewer than 35,000 votes...

 Bloomberg kept his word and even donated money to the education arm of Sharpton’s National Action Network, and, according to Sharpton, never once asked for his endorsement.

Freedlander's piece is missing plenty of details and ignores Bloomberg's predilection for using taxpayer money to pay off some of those same factions, but it's a drive-by assessment of just what he did to get elected and stay in office for term after term despite being really terrible.

Bloomberg skipped debates, made endless gaffes, was cold and unpleasant, didn't campaign all that much, but kept winning because he viewed elections like a corporate takeover. He paid a lot of money to build strong teams and then figured out who to buy, while assuming, correctly, that most people didn't really care all that much. The same method wouldn't work on a national level. And would cost a lot more. 

I doubt very much that Bloomberg can even buy the Dem nomination, but I wouldn't rule it out entirely. Just 98%. The point that Freedlander's flawed article makes is that Bloomberg is a non-traditional candidate and doesn't run for office on his personality or popularity. He does it by analyzing the structure of the field and figuring out how he can reshape the system and its infrastructure to make the impossible, possible.

That's what Trump did.

But Trump has obvious personal and political factors that Bloomberg doesn't. And Bloomberg got away with it because New York City politics was broken and the Dems were struggling at the time. He's not going to succeed at it now.

But, in his campaigning, Bloomberg is the anti-Trump. Trump campaigns around his own personality and brand. Bloomberg effaces his personality. You don't see him, you don't hear him or interact with him. To voters, his victories seem to come from nowhere. Not so to political insiders.