Donald Trump’s romp through the primaries so far has been positively gleeful. On his way to winning seven more states on Super Tuesday, the New York billionaire said of this year’s election: “It’s tough, it’s nasty, it’s mean, it’s vicious. It’s beautiful.”
But if there is anyone as despairing as Trump is gleeful, it’s another New York billionaire: Michael Bloomberg. From his open desk at the headquarters of Bloomberg LP, the financial-data company he founded and returned to as CEO in September 2014, Bloomberg has been watching the primaries unfold with outrage and frustration.
Rarely a day goes by when Bloomberg doesn’t hear Trump say something—such as his declaration that “we’re going to build a wall” on the Mexican border or that climate change is “created by and for the Chinese in order to make U.S. manufacturing noncompetitive”—that makes him want to cough up the free soup served in the Bloomberg snack bar. On virtually every issue, from trade and immigration to gun control and abortion, Trump’s positions are an affront to Bloomberg’s worldview. Even putting aside politics, it would be difficult to find two billionaires who are more stylistically opposed: Trump, the fact-denying, faux populist who jets around in a gilded 757; Bloomberg, the hyperrational, Wall Street–defending technocrat who takes the subway (when he’s not flying his helicopter). Bloomberg’s idea of public service still has the whiff of noblesse oblige; Trump’s is more ignoble megalomania.
What surely galls Bloomberg the most is the fact that Trump has somehow successfully stolen Bloomberg’s core political message: that he’s a job-creating billionaire who can’t be bought by party elites and special interests. What’s more, Trump is actually doing what Bloomberg, who explored presidential runs in 2008 and 2012, twice concluded is impossible. “I am 100 percent convinced that you cannot in this country win an election unless you are the nominee of one of the two major parties,” he told this magazine in 2013. “The second thing I am convinced of is that I could not get through the primary process with either party.”
It is a sign of just how off the rails this election has gone that Bloomberg ever considered revisiting his conclusion about a third-party run. Since December, about a half-dozen of the mogul’s closest political hands have been working in stealth out of the Beaux-Arts mansion on East 78th Street that serves as headquarters of Bloomberg Philanthropies to lay the groundwork for him to jump into the race. Bloomberg’s chief strategist, Doug Schoen, conducted polls showing that voters feel record levels of disaffection for both parties. Kevin Sheekey, Bloomberg’s longtime consigliere, made calls to veteran Democratic and Republican strategists, feeling out potential campaign staffers and strategizing over how they could massage Bloomberg’s anti-gun stance for a pro–Second Amendment electorate. Howard Wolfson, Bloomberg’s former communications director, crafted a national media strategy. Bradley Tusk, who managed the 2009 mayoral campaign, consulted with ballot-access experts about the herculean challenge of collecting the 579,000 signatures required to get on the ticket in all 50 states. “Ballot-access laws are twisted and perverted and evil. They’re designed to keep people off,” says Dallas attorney Clay Mulford, who served as general counsel for the campaign of his then-father-in-law, Ross Perot. Though, given that Bloomberg’s advisers said he was prepared to spend $1 billion self-financing an independent run (Perot spent just $100 million in today’s dollars), it seems ballot access would have been a surmountable obstacle.
Though many have dismissed the prospect of a Bloomberg run as pure fantasy due to the challenging electoral math, a source close to Bloomberg says their research shows he would have a good chance in a Trump versus Sanders race, easily passing the 270 electoral vote mark by winning in New York, New Jersey, Connecticut, Pennsylvania, Ohio, Illinois, Florida, Maryland, California, Georgia, Virginia, North Carolina and Texas. “We’re spending all day thinking and talking about it,” said a member of Bloomberg’s team, who like most of the three-dozen people interviewed for this article would only speak without attribution.
And yet … Hillary Clinton’s post–New Hampshire recovery and crushing Super Tuesday victory has tempered Bloomberg’s lust for the highest office in the land. He’s told friends he does not want to challenge Clinton directly. “He doesn’t want to be Ralph Nader,” a close friend says. Bloomberg and Clinton have maintained a respectful relationship over the years. In fact, in 2012, Bloomberg lobbied her to run for mayor as his successor. At the very least, he is comforted by the fact that the Democratic nominee likely won’t be an avowed socialist.
And so, according to his advisers, Bloomberg is leaning against a run, and may announce that decision soon, but by putting his name out there, he’s joined Joe Biden as a possible backup plan for center and center-left voters terrified by the prospect of a Trump presidency. In the case of a Black Swan event like, say, a Clinton indictment—Trump is already making the case that she “shouldn’t be allowed to run”—Bloomberg could still, potentially, step in. His allies are pushing him as a more viable alternative than Biden or John Kerry in that scenario. “If Bloomberg stepped in, both those guys wouldn’t run against him,” says a friend. It may seem an unlikely turn of events, but this has already proved to be the kind of election where the normal expectations don’t apply. We’ve all become electoral doomsday preppers, with Bloomberg seeing an opportunity to lead us out of the bunker once the smoke clears.
Like most of the professional political class, Bloomberg and his advisers at first dismissed Trump’s candidacy as little more than a stunt. “When Donald Trump announced in June, I did not think he would have the rise and staying power he’s had,” says Doug Schoen. As mayor and a fellow plutocrat, Bloomberg had a cordial, if distant, relationship with the real-estate mogul turned reality-TV star. The two have played in the same golf tournaments, and in 2011, the Bloomberg administration made a deal with Trump to build a $10 million clubhouse and operate a public golf course in the Bronx. “There was no history of animosity,” a former senior City Hall official says.
Bloomberg’s view of Trump darkened as his immigrant-bashing campaign gained steam. “What galled him the most was his divisive rhetoric,” an adviser says. Another Bloomberg associate puts it more harshly: “Michael thinks Trump is a bloviating, bald-faced liar who can’t be trusted on any deals. He’ll tell you dozens of stories about Trump saying things he knows are patently false. Like, how he built the Grand Hyatt in midtown, or donations he’s made, or claims he’s made about friends he lost on 9/11. Michael says those are patently untrue.”
Throughout the fall, Bloomberg received a flurry of panicked calls from friends along the Acela Corridor imploring him to do something to stop Trump. Daily News owner Mort Zuckerman, J.P. Morgan CEO Jamie Dimon, Tishman Speyer chairman Jerry Speyer, and activist investor Bill Ackman all encouraged him to run. Not to mention Rupert Murdoch. “This is Bloomberg’s last chance,” Murdoch tweeted a few days before the Iowa caucuses. “You never know until your hat is in the ring! Events change everything, especially during elections. Nomination.”
While Bloomberg basked in the attention, he remained unmoved. What was most occupying his time was putting his stamp back on Bloomberg LP. When he left City Hall, Bloomberg told people he planned to become a philanthropist on a global scale, à la Bill Gates. But he discovered quickly that philanthropy gave him little satisfaction. “NGO people aren’t his people. He likes money and risk, not deliberation and incremental improvement,” a former colleague says. And so, he went back to his old job.
As part of an agreement with the city he signed as mayor, Bloomberg had been barred from day-to-day involvement in Bloomberg LP while he was in office. And under his hand-picked CEO, Dan Doctoroff, the company had changed in his -absence—starting to look and act more like a traditional media company, expanding aggressively into political and lifestyle coverage.
Employees say that upon his return, Bloomberg seemed frustrated. In meetings, he would talk over Doctoroff. “Why the fuck are we listening to a labor lawyer?” he barked in one budget discussion, according to a person in the room. “Because we have been sued since you left,” a clearly exasperated Doctoroff said.
Weeks later, Doctoroff was out and Bloomberg took over as CEO. “Just remember whose name is on the door,” Bloomberg told a colleague. In December 2014, Bloomberg replaced longtime editor-in-chief Matthew Winkler with Economist editor John Micklethwait, who had a more business-friendly worldview. With 80 percent of Bloomberg LP’s revenues generated by terminal sales mostly to financial firms, Bloomberg instructed Micklethwait to undo some of Doctoroff’s initiatives and focus on the core product of business news for business people. This also meant trying not to alienate Wall Street. “If you are not intrigued by how people make money, are inclined to sneer at those who are good at it, or yearn to practice ‘gotcha journalism’ on investment bankers simply because they’ve chosen to be bankers, Bloomberg is probably the wrong place for you,” Micklethwait wrote in a staff memo.
Those who violated the new ethos quickly attracted Bloomberg’s ire. Last year, he confronted Bloomberg View editor David Shipley after Bloomberg received a call from his friend John Paulson, the hedge-fund billionaire, who was angry about a column. “Mike was furious,” a Bloomberg journalist told me. “He yelled, ‘I don’t like personal attacks on people! This is not who we are!’ ”
Last spring, Trump wrote a scathing letter complaining about coverage of him by Bloomberg Politics and had it hand-delivered to Bloomberg’s Upper East Side townhouse. Afterward, said one high-level Bloomberg source, Bloomberg let it be known that he didn’t want to see personal attacks on Trump in Bloomberg View’s opinion columns. “If you were putting Donald Trump in your piece, you would get special scrutiny,” the source says. Even a relatively mild reference to “P. T. Barnum” was cut. (A source at the company says that Bloomberg View doesn’t publish personal attacks against anyone, and that they have published columns that were critical of Trump.)
Bloomberg’s political reporters weren’t allowed to write much about their boss’s political ambitions either (which caused the Washington news editor to quit in January). This became more and more difficult as his political activities began to ramp up. A few weeks after Trump announced in November that he wanted to create a “deportation force” to go door-to-door arresting immigrants, Bloomberg instructed advisers to conduct a poll to test the viability of a run. What they found encouraged him. “There is such anger towards that system that anytime there’s an alternative it’s beating the Establishment,” says Schoen. “If you run against both extremes and you run in the center, it’s competitive.”
And they imagined Bloomberg as the ultimate moderate. On domestic policy, he’s a proponent of deficit reduction along the lines of the Simpson-Bowles plan, which calls for reasonable tax increases and entitlement reform. He supports comprehensive immigration reform and aggressive efforts to curb climate change. On social issues, he’s a progressive, supporting gay marriage and abortion rights. He’s considered something of a hawk on the Middle East (remember, he supported George W. Bush in 2004). “He thinks the Iran deal is a mess,” a person close to him says. “He thinks we’re coddling them and that it’s probably one of the signal failures of the White House.”
There would be challenges, to be sure. Bloomberg’s unwavering defense of stop and frisk would be a liability in the age of Black Lives Matter protests. And having made $40 billion selling financial data to banks, he’s aligned with Wall Street like few are in an era where bankers are the new bogeymen. And history hasn’t been kind to the idea of a New York mayor running for president. (None has ever made it.) In 2008, Bloomberg’s predecessor, Rudy Giuliani, fared poorly even though he had the post-9/11 benefit of national name recognition as “America’s Mayor.” And Bloomberg would have had the added challenge of being mostly known west of the Hudson (when he’s known at all) for his nanny-state policies. “Have you seen the size of the sodas they drink in the middle of the country?” says Kellyanne -Conway, the president of a pro–Ted Cruz -super-pac.
Still, one senses that it’s hard for Bloomberg’s advisers—and even the man himself—to give up the ghost of a run entirely. After all, they put so much time and thought and analysis into the decision, and Trump, well, didn’t. A private poll Bloomberg conducted in late February showed Trump rapidly losing support from mainstream Republicans after being mocked by Rubio as a con man, retweeting a Mussolini quote, and refusing to immediately disavow the KKK. “That did not go over well,” the adviser says. The same poll showed Bloomberg pulling far more votes from the GOP side than the Democrats.
But GOP donors have explored funding their own third-party candidate, and it would surely not be Bloomberg, given his positions on gun control and abortion. Another Establishment Hail Mary would be to have a moderate like Mitt Romney jump into the GOP race in the New York and California primaries to deny Trump the delegates necessary to clinch the nomination. Then, at a brokered convention, they could name Romney as the party’s standard-bearer. This outcome, too, would leave little room for a Bloomberg run.
Even if there were an imperfect-storm scenario that created a third-party opportunity for Bloomberg, it would have to happen fast. According to Bloomberg’s advisers, he would have to begin gathering signatures in Texas and North Carolina within the next few weeks to ensure he’s on the ballot in those delegate-rich states.
Friends and colleagues say Bloomberg’s political frustrations are only intensifying his desire to secure a third act to his career. One person close to Bloomberg suggested he would be happy serving in a Hillary Clinton administration, should she win. “I think she’d offer him Treasury, but he doesn’t want Treasury. He wants Defense,” the source says. “Think about it. The Pentagon is a mess in need of innovation and reform. And it would be a pseudo foreign-policy role for him.”
Bloomberg’s lack of military experience surely makes this a stretch, but it’s another sign of his ambition at this late phase of his career. (A source close to Bloomberg says he has no interest in this.)
“Mike is bored,” says a friend, to which an advisor adds: “He knows this is his last chance do a final act in his career. He’s 74 now. You can’t do it when you’re 77.”
He can’t seem to help himself from dipping a toe into the national political waters. In a recent speech, Bloomberg talked about his view of the problems facing the country: “wage stagnation at home; American retreat around the world; and a corrupt, gridlocked, and broken two-party system that answers to lobbyists and special interests instead of the American people.”
“The message is,” says a top adviser, drafting a stump speech that will likely never be given, “you’ve got a guy who is one of America’s most successful businessmen who has a proven record in the public and private sectors creating thousands of jobs. He’s someone who’s worked with both parties to achieve results. He’s never taken a dime of campaign contributions and he doesn’t owe special interests anything. He’s an outsider of the system who also knows how the system works. That’s a powerful message.”
But Bloomberg may have to content himself with having already won in one respect: He’s back in the conversation. In January, at the annual Alfalfa dinner in Washington, D.C., grandees lined up to kiss his ring. “People were coming up to him saying ‘I’m so glad you’re going to run!’ ” a guest recalls. Bloomberg, the third-time almost-ran, just beamed.
This post has been updated to clarify Bloomberg View’s position on publishing personal attacks.
*This article appears in the March 7, 2016 issue of New York Magazine.