Michael Bloomberg’s bully bid for the White House

The latecomer to the Democratic race is trying to win the U.S. presidency the old-fashioned way—by buying it
Judge Judy Sheindlin and former New York Mayor Michael Bloomberg, a Democratic presidential candidate, eat lunch at a barbecue restaurant in San Marcos, Texas on Jan. 11, 2020. Sheindlin, the no-nonsense TV mega-star, is breaking five decades of political silence to publicly back a politician that she sees as the only one who can "help American heal." (Ilana Panich-Linsman/The New York Times/Redux)

The wealthiest person ever to hold elective office in the history of the world selects four strips of marbled brisket, a side of beans and a dish of crinkle-cut pickles. Shuffling ahead in the queue, casually dressed in an open-necked shirt and a pullover but sporting neither the 10-gallon Stetson nor the rattlesnake boots appropriate for the locale, he pulls a pair of twenties from his wallet, in case the cashier at the barbecue shack in San Marcos, Texas, can’t break a billion-dollar bill.

Waiting at Michael Bloomberg’s table is a fellow New Yorker, thin-faced, bright-eyed and famous. Her date lifts two slices of beef off his plastic plate and forks them onto hers. She’s the television magistrate everybody knows as Judge Judy, sharing an early bird special with 2020’s most intriguing late arrival—the golden ager with 60 billion frijoles who wants to cashier poor Donald Trump.

For Bloomberg—the Boston-born business-data magnate who served three terms as mayor of the Greatest City in the World, steadying and refocusing New York, N.Y., after 9/11—the outpost of San Marcos, between San Antonio and Austin, is as alien as Ganymede. (It is just as otherworldly for Judy Sheindlin, the woman by his side on this January campaign swing. Judge Judy was a schoolmate of Sen. Bernie Sanders in Brooklyn, N.Y., back in the long ago. Sen. Chuck Schumer and Supreme Court Justice Ruth Bader Ginsburg attended that same academy. It must have been a wild prom.)

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The beef-eaters are city people from horns to tail. Bloomberg, despite his Massachusetts roots, is (and sounds) as New York now as pigeons, yellow cabs and the Plaza. But there are votes out here—votes that may decide the Democratic primary this spring, long after Iowa and New Hampshire are forgotten—and so the rich man goes west, if not patronizingly Western. “America is not New York, I understand that,” Bloomberg avows on this one-day, five-city campaign tour of the Lone Star State. Yet he is seeking—even expecting—that America will abandon every other Democratic candidate between now and April and hand the nomination to him. He has never campaigned for national office before, but then neither had Donald J. Trump.

Bloomberg’s multi-billion-dollar philanthropy to medical and educational institutions; his impassioned support for gun control and environmental causes; his famous onslaughts as mayor against public smoking, Styrofoam packaging, heart-stopping trans fats, “heavy” heating oils and big-slurp sodas—all of these positions could weigh favourably on voters’ minds in the fall.

But first, the party-shifting magnate, who won his first term as mayor as a Republican, and who endorsed George W. Bush for re-election in 2004 at the nadir of the Iraq War, must win the Democratic nomination.

This winter, he is attempting to win it the old-fashioned way—by buying it.

Born on the first Valentine’s Day after Pearl Harbor, Michael Rubens Bloomberg is not an orator, not a demagogue, not a Barack Obama. His rallies attract serious, curious voters of all ages, but only by the dozens and hundreds. On the stump, physically smaller than his money might inflate him in an audience’s eyes, he strives to deliver his talking points, get off a self-effacing quip or two, shake a few hands and get back on his bus.

In Chicago last month, commending a recent graduate who had landed an executive-level job at McDonald’s, he described himself as “more of a Subway sandwich guy. I could have the BMT every meal for the rest of my life, no oil or cheese or extra vinegar, please.” In Texas, staffers try to whip up chants of “I like Mike,” but these are soon lost to the prairie wind. Instead of a plangent plea for Hope or Change, Bloomberg’s tag line is terrestrial and blunt: Mike will get it done.

If elected in November, he would be the oldest man to assume the American presidency, but so would Bernie Sanders or former vice president Joe Biden. (Bloomberg or Sanders would be the first Jew.) The only person of comparable affluence to actively seek the White House was the auto industrialist and virulent anti-Semite Henry Ford, who expected to be acclaimed as both the Democratic and Republican candidate in 1918 and 1924. He wasn’t. No latter-day Jobs or Zuckerberg or Bezos—no Buffett or Winfrey or Gates—has tried.

In Texas, Bloomberg’s talking points are concise and, like the Wall Street analytics that made him the Midas of business media, driven by hard statistics:

“We reduced the number of uninsured people in New York by 40 per cent . . . ”

“We raised life expectancy by three whole years . . . ”

“We reduced the city’s carbon footprint by 14 per cent . . . ”

He rises to his crescendo, which is about as animated and jocular as Michael Bloomberg gets:

“When I am in the Oval Office, NO MORE TWEETING!”

No former New York City mayor has won the presidency. None has gained a major party’s nomination since DeWitt Clinton in 1812. Rudy Giuliani, once a front-runner, imploded in 2008. The current His Worship, Bill de Blasio, joined the Democratic race in May 2019 and flamed out four months later. But no former New York City mayor ever had as much dough as Michael R. Bloomberg.

Nor have many Americans given so much away.

“From my perspective, he has been a visionary donor wanting to see his resources lead to a tremendous amount of good in the world,” Dr. Joshua Sharfstein tells Maclean’s. Sharfstein is a former Obama administration official who now serves as the director of the Bloomberg American Health Initiative at Johns Hopkins University in Baltimore. (Bloomberg has gifted more than US$3 billion to his alma mater and its affiliated hospitals and institutes.) “He cares deeply about counting the number of people whose lives are saved or transformed. He brings to philanthropy the same spirit he brought to being mayor—of really wanting to know that what he is doing is working.”

Bloomberg in San Antonio, Texas (Bonnie Arbittier/Rivard Report)

Last November, after years of vacillating on a run for the White House, and after two dozen other women and men had been on the trail for months, Bloomberg finally declared his candidacy. Playing catch-up, he opened his wallet and lifted out a lot more than a pair of twenties.

Thus, when the Tennessee Titans led the Baltimore Ravens, 7-0, in the first quarter of their National Football League playoff game in January, Bloomberg appeared between the car commercials and the credit-agency ads, touting his humble beginnings and his only-in-America ascent.

Spending US$40 million of his own money every week in the early stages of his campaign—and with the ability to dial that number much, much higher—his image and message were everywhere: on the Jeopardy! Tournament of Champions, on the daytime soap operas, on the The Great British Bake Off, on YouTube whenever you went to watch an old Queen video or your daughter’s high-school play.

Only in the supposedly determinative “early states” was Mayor Mike invisible. Corny Iowa, ice-block New Hampshire, racially divided South Carolina, high-rolling Nevada—Michael Bloomberg bypassed them all in favour of Texas, California and the other “Super Tuesday” bailiwicks that will vote in early March. If his strategy succeeds, the tradition-filled trudge to the hinterlands will never happen again. All it will take to win will be a bottomless barrel of airwave-flooding, internet-saturating, repetitive, repetitive, repetitive, repetitive, repetitive, repetitive cash.

“I have been very lucky in business,” Bloomberg shrugs in Texas, explaining how he can afford this game.

“If you had a couple billion dollars, you could announce your candidacy for president and be taken seriously, even if you were the dumbest person on earth,” Bernie Sanders fist-shook in reply. “The American people are sick and tired of the power of billionaires.”

How wealthy is the wealthiest politician in history?

In 2018, the U.S. Federal Reserve reported that 40 per cent of Americans do not have enough money in the bank to raise $400 in an emergency.

Michael Bloomberg could gift every one of those struggling citizens with four hundred bucks and still have $10 billion left over for brisket. Hatless in San Marcos, Texas, he doesn’t need to pass the sombrero anywhere else, either.

The Martin Luther King Jr. Day service draws only a few dozen communicants to “the oldest Black institution in New York state”—the Mother African Methodist Episcopal Zion Church on West 137th Street in Harlem, New York City. As much as a defiant Freedom Tower rising from the ashes of the World Trade Center, nanny-state restaurant-menu calorie counts and the traffic-free “Bloomberg zones” along the major avenues of Midtown are Mayor Mike’s legacy, this is his New York, too.

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A visiting pastor from New Jersey holds the Mother Church pulpit, railing and wailing against the current commander-in-chief—“A corrupt and immoral president who was elected not by the people but by Russians!” the Reverend Stephen A. Green fire-breathes. “A God who has been with us through slavery, a God who has been with us through Jim Crow, a God who has been with us through Ronald Reagan, will certainly be with us through Donald J. Trump!” he assures the worshippers.

Yet to some Harlemites, Mayor Bloomberg is as reviled as Trump is.

For most of Bloomberg’s 12-year mayoralty, his New York Police Department engaged in a practice called “stop and frisk”—an ostensible crime-reduction initiative that saw officers briefly detain and search people, as often as 700,000 times each year. Most of the persons who were patted down were young men of colour. Barely 10 per cent of them were found to be engaged in criminal behaviour.

Concomitantly with the program, or merely coincidentally, the city’s crime rate dropped sharply. In fact, street assaults declined so comfortingly that white developers began wrapping their tentacles around the superb old architecture of now non-threatening Harlem, and so many tourists began taking the A Train that, as one long-time resident was saying on MLK Day, “all these people coming from Europe act like we’re a petting zoo.”

“ ‘Stop and frisk’ keeps New York safe,” Mayor Bloomberg wrote in an August 2013 issue of the Washington Post, doubling down.

“I was wrong, and I am sorry,” he about-turned in November 2019, having decided to run for president. Then this, on Martin Luther King Jr. Day of 2020: “His apology is too late and, in many respects, offensive,” Brother Abraham Williamson of Mother Zion tells Maclean’s. “Why not remove that policy while you are actually IN power instead of apologizing for it later?

“What that policy said in this part of New York City was that if I walk down Lenox Avenue, even with my three graduate degrees, I am a suspect. That tactic will take three or four generations to heal.”

Tote bags are handed out to supporters of Democratic presidential candidate Mike Bloomberg at Central Machine Works in San Antonio, Texas on Jan. 11, 2020. (Mark Felix/AFP/Getty Images)

On this same holiday, Michael Bloomberg is in Tulsa, Okla.—the site of a racist massacre in 1921 that killed 200 Black citizens—announcing a plan to invest US$70 billion in public funds into banking, housing and business initiatives to lift African-Americans into the middle class if he is elected president.

“My story would have turned out very differently if I had been Black,” Bloomberg says.

“BLOOMY’S BLITZ FOR BLACK VOTES,” hoots the Daily News.

“The day Bloomberg announced that he was running for president,” says a parishioner named Ruth McDaniels, “I went straight to his office on 125th Street and I asked his people, ‘What does that mean to us in dollars and cents?’ All those people he put in prison, how do we process that?”

McDaniels, a former NYPD officer and chaplain who now heads an anti-violence organization called Breaking the Chains of Your Mind, is the same woman who was complaining earlier that some foreign tourists seem to consider the people of Harlem to be a herd of domesticated beasts.“I believe that, to whom much is given, much is required,” she says of Michael Bloomberg’s political aspirations. “His policies are problematic. He doesn’t listen to the people. He turned New York into a playground for the wealthy. If that’s what he wants for New Yorkers, is that what he wants for the country?”

McDaniels pauses.

“One thing I do appreciate,” she says, “is he took smoking out of the buildings, and that heavy oil, and his campaign against sugar.”

“This is not a time for all talk, no trousers,” Judge Judy propounds at a stop at Market Square in San Antonio.

“I looked at the rest of the field and I said America is the greatest country in the world and it deserves greatness,” she continues. “And I looked at everybody else and I said, ‘I don’t see greatness there.’ Everybody else out there is just a lot of noise.”

This is happening at a cantina named Viva Villa, which are precisely the two words that a posse of rifleman mockingly shouted in 1923 as they ambushed and assassinated Francisco “Pancho” Villa, the Mexican revolutionary, ranchero, cultural icon, brazen invader of the United States of America, and, to some, Robin Hood.

The populist Pancho, whose face is painted on the café wall, might not have approved of Michael Rubens Bloomberg (or anyone else) owning US$60 billion. But the 100 or so Democrats at the rally do not seem troubled by the fact that the richest vote-seeker since Henry Ford may well be leading their team of banditos come November. “I think he earned it the right way and I have no problem with people who accumulate wealth in the right way,” says a San Antonio businessman named Bill Ward. “I wish I had more wealth.”

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“I don’t think that his intent is malevolent,” agrees Derick Monewitz, visiting from Illinois. “It doesn’t bother me that he is wealthy. It doesn’t bother me that he is self-funding. I think he is a serious candidate who is not in this to blow it up. I see him as a problem-solver, not an ideologue.”

“Mini Mike Bloomberg doesn’t get on the Democrat Debate Stage because he doesn’t want to—he is a terrible debater and speaker,” the blower-upper in the White House, clearly nervous, posts on Twitter during this time. “If he did, he would go down in the polls even more (if that is possible!).”

(Like a grizzly rearing on its hind legs to tower over a perceived threat to her cubs, Donald Trump often tries to downsize the opponents he most fears. Hence, “Little” Marco Rubio in 2016, “Little” Adam Schiff in the impeachment trial, and now “Mini Mike.” The epithet makes it clear how frightened the incumbent is of Bloomberg’s candidacy.)

“I want to debate, but I don’t qualify because I’ve never taken a penny in contributions from anyone. Not even a ‘very small loan’ of a million dollars,” Bloomberg punches back. A Subway Series in the autumn between the two New Yorkers would be a heck of a brawl.

“You’re going to have an election in November, and you’re going to need someone who can stand toe to toe, who understands the incumbent, and who understands and appreciates how to manage him. I think he’s the only one who can do that,” Judge Judy endorses, deep in the heart of Texas.

“I don’t think we need a revolution in this country, I think it’s the greatest country on earth. Everybody wants to come here. Nobody’s asking for a permanent exit visa out of the United States of America. Everyone wants to come here. That doesn’t sound to me like a country that needs a revolution.”

John WaRne Gates was a steel, coal and railroad baron whose fantastic wagers on horse races, poker—even two raindrops sliding down a windowpane—earned him the nickname “Bet-a-Million.”

Gates died in 1911. Now comes Bet-a-Billion Bloomberg.

“The good news about him is that he could start immediately and run the country and you would feel that you are in good hands,” former New York City councilwoman Gale Brewer, now the borough president of Manhattan, tells Maclean’s. (Brewer was a convention delegate for Hillary Rodham Clinton in 2016.) “He’s on time. He’s on topic. He’s very data-driven. He’s not afraid to sit and talk to you. He doesn’t mind you asking stupid questions—and he does his homework.

“To his credit, he could balance a budget. He has big ideas about how to improve things. I think he truly thinks that, because he did it, people can pull themselves upward in life.”

“How did he win the mayoralty in the first place?” Brewer is asked.

“Money!” she snips. “I was running for the city council at the same time. We had volunteers, but you always heard that he paid for his petitioners to go door to door. He was worth $10 billion back then. Now he’s worth $50 billion, but that doesn’t help him. People may think, ‘You’re too rich to be helpful to me.’

“His ads are excellent in countering that. I think people think that you need an SOB to beat Trump, but you don’t. You need ideas. He’s moving up now. But I think people want to be touched by someone, and that’s a problem for Bloomberg.”

Closer to the presidency than any man of his means has ever been before, Michael Bloomberg’s task remains far from easy—no matter how many ads he can place on the The Great British Bake Off. It is getting late in the campaign to be an early bird, and late in American history to sell a low-key message of probity, public service and truth, while a man in a high tower on Fifth Avenue watches and waits.

“How do you think Michael Bloomberg would handle losing?” Gale Brewer is asked in the Greatest City in the World.

“I don’t know,” the borough president replies. “He’s never lost.”

This article appears in print in the March 2020 issue of Maclean’s magazine with the headline, “A bully bid for the presidency.” Subscribe to the monthly print magazine here.