One of Manhattan’s favorite parlor games these days is to discuss the presidential prospects of Michael Bloomberg, New York City’s favorite multi-billionaire ex-mayor. Although Bloomberg hasn’t made any announcements yet about his 2020 candidacy, he has taken a number of meaningful steps in its direction—steps that make it clear he’s serious this time and is not overthinking as he did in 2016. He donated $100 million to support a host of Democratic candidates in the midterm elections, helping to pick up forty seats in the House, and purchasing plenty of goodwill in the process. In October he made it official, formally re-registering as a Democrat after running New York City as a Republican and then as an independent. (The Democrats, he explained, can “provide the checks and balances our nation so badly needs.”) Bloomberg also made quite the splash last week by announcing that he was donating $1.8 billion to Johns Hopkins, his alma mater, to make it possible for low-income students to attend the university without having to worry about tuition. Bloomberg has now donated a total of $3.35 billion to the school—among the largest individual gifts ever made to support higher education.

These moves underscore a highly relevant fact about Bloomberg: he is the anti-Donald Trump. He is philanthropic, where Trump is not. He is actually very, very rich—with a net worth of more than $50 billion and counting—whereas Trump mostly pretends to be. He has meaningful and relevant experience as the chief executive of a global company and an international city, while Trump was woefully unprepared to be president and seems always to be learning on the job, and poorly at that. Unlike Trump, who at 72, claims to be the healthiest person who has ever served as president, Bloomberg, four years older than Trump, may actually be among the healthiest. In any event, he has some serious longevity genes: his mother lived to be 102 years old.

Being the anti-Trump in nearly every way, shape and form could prove extremely useful politically for Bloomberg should he decide to run in 2020. And there is little doubt that whomever the Democrats nominate to face Trump, the plan will be to draw as sharp a contrast with him as possible, hoping that by then a vast majority of Americans, as well as the Electoral College map, will have had quite enough of Trump and his presidency. The only unanswered question is whether the Democrats will nominate someone from its liberal progressive wing—in the Elizabeth Warren, Bernie Sanders, Kamala Harris, Beto O’Rourke mold—or whether the nominee will be from the party’s centrist progressive wing, in the form of, say, Bloomberg or Deval Patrick, the former governor of Massachusetts who has been a Bain Capital partner for the past three years.

No surprise, on Wall Street, Bloomberg has vast reservoirs of support. “Think he would be great for America, and therefore for Wall Street,” one senior banker e-mailed me the other day. “Can’t think of anybody else I’d rather see win frankly.” Added Christopher Whalen, the founder of Whalen Global Advisors, an investment banking firm, and an astute economic analyst, “Oh, I’d vote for Michael in a heartbeat because he’s competent. In most areas you and I care about, he would do a good job.”

But for both men, the question remains: Can Bloomberg win? The senior banker thinks Bloomberg could win the popular vote, although he’s less sure about the Electoral College. “The number of voters who would want almost anybody (except Hillary) over Trump exceeds the number of core Trumpers,” he wrote. “Bloomberg vs. Trump: he gets all of the Democrats and a big slug of Republicans as well.”

Still, what works for Wall Street doesn’t necessarily resonate on Main Street. Whalen worries that Bloomberg doesn’t have the “public persona” to run for president—he’s just not well enough known beyond the Hudson—and may come off as “preachy,” on such topics as gun control, smoking, and the consumption of sugary drinks. Large swaths of the American electorate obviously don’t like to be told what they can and can’t do and what may or may not be bad for their health, despite the fact that Bloomberg is probably correct about the dangers of smoking and consuming too much sugar, to say nothing about the need for comprehensive gun control.

Bloomberg’s strident position on guns could be the most damaging, if the plan is to pick up Republican support. “Michael is toast in every Red State because of that one issue,” Whalen explained. “That kills it. Even in states like Maine and New Hampshire, which are arguably Blue States now, he would still lose on that issue. The downstate vote wouldn’t be enough to fix it. Out West, forget about it. He comes across as a New York Jewish guy who hates guns. It’s like, no. They’ll put him together with the pantheon of Democratic politicians and Elizabeth Warren. Imagine Mike Bloomberg and Elizabeth. There’s a ticket for you.” He thinks that while Bloomberg “fits the mold” of a very mainstream Democratic politician “that we’re screaming for” and that he would make a good president, to win Bloomberg will have to “pull in his horns” on the issue of gun control. “If he wants to win Texas or Ohio, you don’t go in there proposing that we ban guns,” he said. “That’s just not going to fly. Definitely not. You got to tone down the New York bit and do more of the international businessman, I think.”

The inside word on Wall Street is that Bloomberg will announce his candidacy in February. And that’s when the trouble for him will start, and not just from Trump, who many believe Bloomberg can face down in ways that his rivals for the Democratic nomination cannot. No, the problem for Bloomberg will come from the progressives to his left. “Oh God, please don’t run,” read one characteristic response in The New York Times comment section in September, after the paper ran a piece about the prospects of a Bloomberg presidential bid. “I respect him tremendously on gun violence prevention and on the environment. But this is a man who ran and governed as a Republican. He is not what Democratic progressives want or demand at this time. And let’s not overvalue the middle—Democrats playing to the middle for too long is partly to blame for two branches of government now being in Republican hands. He will do nothing to inspire people who often don’t vote and help us get out the Democratic vote. Getting out the Democratic vote is what it’s all about.”