Honestly, we should be kicking ourselves. Of course former New York mayor Michael Bloomberg is now, once again, flirting with entering the 2020 Democratic presidential nominating contest.

After all, there has been at least some form of Bloomberg-is-running static for each of the past three contests. In 2007, while he was mayor and during his last few months as a Republican, he talked to possible supporters about a 2008 run. In 2010, now an independent, his allies were at it again, trying to figure out how to make 2012 happen. In 2016, Bloomberg used a possible presidential run as a cudgel: If the race came down to Donald Trump against Sen. Bernie Sanders (I-Vt.), he would have no choice but to weigh in as a sensible alternative. In March of that year, he figured Hillary Clinton was good enough and decided against running.

Bloomberg’s spasmodic discussions about running for president are so well-established by now that this is the second time we’ve been through this in this cycle alone. Seven months ago, he said he wouldn’t run, and yet here we are.

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But again, we should have predicted this happening now. Bloomberg is a billionaire, and the past few weeks have seen a flurry of other billionaires expressing public consternation about the rise of Sen. Elizabeth Warren (D-Mass.) in the polls. One wrote a long, sad-sack letter complaining about her policy proposals and rhetoric. On Wednesday, former Microsoft CEO Bill Gates crankily objected to Warren’s tax proposals, suggesting hyperbolically that he’d have to pay $100 billion in taxes — leaving him with only the equivalent of 110,000 years of the median annual household income to subsist on.

There are more esoteric factors at play, too. Bloomberg would be forgiven as well for assuming that if voters were looking for a self-made billionaire with a lot in the bank, he had a lot more to offer on both fronts than the guy in the Oval Office. (The Democrats have a billionaire in the race, Tom Steyer, but he’s not making much of a dent.) Heck, it’s even a boom market for media coverage for former New York mayors. How could he miss?

When Bloomberg was last toying with the idea of running in 2020 and before Steyer jumped in, we raised what seemed at the time like an obvious point: Why do these guys think that the candidate Democratic voters will find most appealing is a white, male plutocrat? We walked through all of the reasons to think that was precisely not what Democrats wanted, given that the party has grown sharply more liberal in recent years and given that the strong 2018 election for the party was powered by nonwhite candidates and women. (Bloomberg’s longtime political adviser Howard Wolfson sought to give Bloomberg some credit for the outcome of that race, noting that Bloomberg had invested $100 million in the outcome.) A poll from Gallup last month found that Democratic voters are more satisfied than usual with the field as it currently stands.

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Part of the motivation, certainly, is the self-confidence that comes with having earned more money than one could spend several generations of lifetimes. Some billionaires seem more willing to conflate net worth with personal worth than most people, in case you hadn’t read the news in the past few years.

What’s more, while the Democratic Party of 2019 seems like a weird place for a fairly moderate, pro-business white guy to land, there’s not really anywhere else for him to go. As we’ve noted before, a lot of never-Trump Republicans have grafted themselves onto Democratic political conversations simply because there’s nowhere else to go. What’s a party-fluid guy like Bloomberg going to do, run third-party? Primary Trump?

It’s just … a weird fit. In June, the Associated Press and NORC asked Americans what qualities in a presidential candidate would make them most appealing. The factors that would generate the most excitement. Both overall and among Democrats, the most appealing quality was experience in elected office, which Bloomberg certainly has — although so do most of the other Democratic candidates. In both groups of respondents, three of the least exciting qualities were a candidate who is old (check), one who is white (check) and one who is a man (check).

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Incidentally, our saying the 77-year-old Bloomberg is old isn’t our being rude to the former mayor. Bloomberg said that he was “a little bit too old” to run for president.

He said it 22 years ago, on CNN’s “Crossfire.”

He does have one fairly well regarded quality that much of the field doesn’t: that business experience. In the AP-NORC polling, though, a strong business background was seen as more appealing from the electorate on the whole than among Democrats. (On the graph below, dots above the line are traits more popular among Democrats.) A business background was about as appealing to Democrats as a black candidate, and it was quite a bit less appealing than a younger candidate or a woman.

There’s a big asterisk hovering above those results, of course. Democrats may say they aren’t really excited about an old white man as a candidate, but, if so, no one’s told the plurality of the electorate that supports former vice president Joe Biden. Biden has led the field for most of the year, suggesting that an older white guy might just make it after all.

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Biden’s poll numbers are predicated heavily on his moderate positions and his support from black Democrats (two groups that overlap significantly). If Bloomberg’s going to make a dent, he’s going to have to eat into Biden’s dominance with that pool of voters.

Which is where Bloomberg’s sketchy history becomes important. It seems pretty unlikely that Bloomberg will peel away much of Biden’s support with black voters, given his advocacy for — and ongoing defense of — stop-and-frisk by New York City’s police department. That policy overwhelmingly targeted nonwhite residents of the city and had no apparent effect on the New York’s violent crime. It’s a policy that Trump has forcefully endorsed, which doesn’t suggest that it’s something Democratic voters will embrace.

There are also questions about Bloomberg’s history with women at his eponymous media company. When harassment allegations from multiple women arose 20 years ago, he called them “out-and-out extortion.” At another point, he claimed that he was being targeted because he was well-known. These assertions might also sound familiar.

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I have certainly been wrong about the political chances of New York billionaires seeking federal office before. It’s just hard to see, in this specific case, how a late entry by Bloomberg makes a significant run at Biden. Throwing money at the race only buys you a few percentage points, at least the way Steyer’s throwing it. Battling Biden on his turf may, in fact, increase the odds that Warren is the nominee, given that it’s safe to assume Bloomberg voters will be coming from moderates currently in the field like Biden or South Bend, Ind., Mayor Pete Buttigieg.

Why do it? Bloomberg’s past success has probably given him a sense that he can accomplish unlikely things. He probably has some non-billionaire consultants in his proximity who are happy to help him spend a small fortune on a race, a small fortune that for Bloomberg is barely a blip. Why not do it, really, when you’ve got no shortage of self-confidence and dollars?

And who knows? Stranger things have very much happened.

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