Michael Bloomberg is so wealthy he couldn’t fritter away his fortune, even if he tried. But he’ll make a good start if he spends $100 million or more to win the Democratic presidential nomination. It’s a fruitless quest.

He must be smart enough to know it. That’s why he is merely “exploring a run” and hasn’t jumped in yet. Still, the glittering prize of 1600 Pennsylvania Ave. dazzles even the shrewdest eyes, and it may have dazzled Bloomberg’s.

Running would be a rare mistake in a career that led him to vast riches and the mayoralty of America’s largest city. (It’s no South Bend, but there are those who love it.) Bloomberg made his money by recognizing a lucrative gap in the market for economic information. To trade stocks, bonds, currencies, and commodities, market participants need real-time information, bundled with sophisticated software to make sense of it. Bloomberg saw the need, thought he could fill it better than anyone, and could charge steep fees to do it. He was right, and he executed his design perfectly. He is still tops in the field, still making a mint from it.

Now, Bloomberg sees another gap, this one in the Democratic presidential field, where no center-left candidate dominates. Both Joe Biden and Mayor Pete Buttigieg have obvious weaknesses and Amy Klobuchar has all but disappeared. Bloomberg is right in saying the whole field is weak, most candidates are too far left to win in November, and the center lane is not too crowded. He’s also right in saying that President Trump is vulnerable despite the strong economy. And he’s right in thinking that his age is no barrier. At 77, he is still energetic and sharp enough to do the job.

Where Bloomberg is wrong is thinking he can captivate a Democratic base that has moved sharply left since Barack Obama left office. He’s wrong, too, if he thinks policies that worked in New York City will appeal to contemporary Democrats.

Bloomberg’s problem is not that primary voters hate his notorious tax on Slurpees or his strong stance against guns. They like them. Party activists don’t drink Big Gulps; they sip fair-trade coffee and craft beer. They don’t drive pickup trucks with gun racks. Au contraire. They think restrictions on gun sales are long overdue and will reduce urban crime. They adore government policies crafted by experienced professionals, not gasbag populists. Some remember Bloomberg’s New York as a very competently run city, one that became cleaner, safer, and more prosperous during his tenure (2002-2013). So far, so good.

The problem is that Bloomberg made the city safer by cracking down on petty criminals (“broken windows” policing) and frisking lots of people to lessen gun violence. Those policies, begun under Mayor Rudolph Giuliani and continued under Bloomberg, worked well—but they made enemies, especially in poor, minority neighborhoods. Today, those policies are despised by party activists, especially African Americans.

Being strong on crime is the surest way to alienate today’s Democratic primary voters. The same black politicians who backed tough laws during the crack cocaine epidemic now reject them and blame their passage on white racists. (That’s why Joe Biden, who voted for these bills, now apologizes for them.) Actually, black politicians were among their strongest advocates. Back then, they had plenty of support from minority voters living in communities ravaged by crack and the gangs that sold it.

Those days are gone. The politicians who previously supported such policies now revile “mass incarceration” and the “prison-industrial complex.” For them, Black Lives Matter means no more intrusive policing, no more arrests for “broken windows” or jumping turnstiles, no more street stops to frisk for illegal weapons.

Gone, too, are the days when reform-minded Democrats supported charter schools, as Mayor Bloomberg did. Teacher unions have waged war on them in Democratic cities across the country.

This shift in attitudes means Bloomberg can tell primary voters he made New York more livable, but he cannot tell them how. His successful policies are now politically toxic, at least among Democrats. They are major obstacles to winning black support, an essential element in the party’s coalition. Elizabeth Warren and Mayor Pete face their own obstacles with this vital constituency, where they badly lag Barack Obama’s vice president.

Bloomberg’s second problem is yet another one that would be a huge asset in a sane world. He is the very embodiment of an American economic success story. He is immensely rich, and he made it all himself. Republicans love that kind of story. Democrats once did, too. No more. It doesn’t matter that Bloomberg made his riches honestly by adding value to the economy. He didn’t throw poor people out of work, run sweatshops, mine coal, or slaughter cuddly animals. It hardly matters that he’s given away billions to charity. What matters is that he is not embarrassed by his riches, that he made them in the financial sector, and that he opposes the activists’ anti-growth policies, such as the Green New Deal. For the socialist wing of the party, those are the indelible marks of Cain. The hard left will never back him, even if he wins the nomination. Some might hold their noses and vote for him in the general election, but his nomination would rip the party apart.

Bloomberg faces other problems, too. He is the opposite of charismatic. He lacks a national, grassroots organization. His money can buy consultants and advertisements, but it cannot coax volunteers to ring doorbells. His strong position on gun control has given him some national stature, but the local candidates he backed mostly lost, despite his generous campaign donations. His late start in the presidential race doesn’t help either. He will miss the early primaries. In short, he has never proved he could win — or generate much enthusiasm — beyond a small island off America.

Surely, Mike Bloomberg knows all this. So why run, aside from feeding his ego? One possibility is that it could put him in line for the vice presidency. He could certainly help fund a national campaign, sure to be brutally expensive. But that, too, is a long shot. A party so deeply immersed in identity politics will push hard for a woman on the ticket (if the nominee is a man) or a minority (if the nominee is white).

These formidable obstacles leave Bloomberg with only a narrow path forward. He’s an immensely talented, successful businessman, but he’s also a dull campaigner who opposes the left’s most ambitious programs. He has little support among minorities or public-sector unions. In today’s Democratic Party, that’s an awkward spot from which to seek the nomination. His yacht is more likely to hit an iceberg than sail safely into harbor.