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Michael Bloomberg facing off against Donald Trump
Photo illustration by Sarina Finkelstein for Money; AP; Getty Images

Former New York City mayor Michael Bloomberg is expected to endorse Hillary Clinton for president at the Democratic National Convention tonight in Philadelphia.

That’s a coup for the Democrats, who sometimes struggle to present themselves as a party that the business class can warm up to.

Bloomberg, of course, is a self-made billionaire who went on to lead the Big Apple for a dozen years starting months after Sept. 11. In other words, to many New Yorkers, at least, Bloomberg is the real tycoon-turned-public-servant that Donald Trump plays on television.

But here is what you need to know about Gotham’s two most famous billionaires to decide for yourself.

Net worth:

Bloomberg: With an estimated $38.6 billion to his name, according to Forbes, Bloomberg ranks as the eighth-richest person in the world. He is the founder, 88% owner, and chief executive of Bloomberg LP, a company that makes its money selling financial data to Wall Street.

Trump: Trump puts his own net worth at $10 billion. Like Bloomberg LP, however, the Trump Organization is privately held, making a precise figure impossible to calculate. Much like the Trump brand, The Donald's own estimate is widely thought to be aspirational. Earlier this month Bloomberg—the news arm of Bloomberg LP, not the man—estimated Trump's net worth at $3 billion, based largely on the value of his golf courses and office buildings. Forbes pegs it at a somewhat more generous $4.5 billion. One Trump critic suggested in a 2005 book that The Donald's net worth was a mere $150 million to $250 million, provoking a lawsuit. (It was eventually tossed out of court.)

Business record:

Bloomberg: Largely a self-made man, Bloomberg founded Bloomberg LP in 1981 with a $10 million severance check that he received after being fired from investment bank Salomon Brothers in 1981. The company, which developed desktop computer terminals that allow investors to crunch reams of data and communicate electronically nearly a decade before the advent of the World Wide Web, now employs more than 19,000.

Trump: Along with his siblings, Trump inherited a New York real estate empire from his father in 1974. His share is estimated to have been worth about $40 million, or $195 million in today's dollars. While Trump has certainly grown his net worth in the more than 40 years since, that doesn't necessarily signal extraordinary business acumen: Observers have pointed out that merely investing $40 million in the U.S. stock market in 1974 would have produced more than $2 billion today. What's more, Trump's numerous brushes with bankruptcy, not to mention involvement with questionable enterprises like Trump University, suggest he is more of a financial engineer and escape artist than job-creator.

Management style:

Bloomberg: Like Trump, Bloomberg ran for office on his management know-how. He soon became known for a no-nonsense, data-driven approach to city problem-solving. Some of his prominent innovations: Doing away with the ornate Mayor's office in favor of a desk in an open-plan setting; setting up a 311 telephone help line to field non-emergency complaints; banning smoking in restaurants and bars; and re-organizing the city’s schools. Not that Bloomberg is without his critics: His failed attempts to limit traffic in mid-town Manhattan and curb soda sales earned him a reputation as something of a killjoy.

Trump: Never accused of being a killjoy, Trump's roomy memorabilia-stuffed Trump Tower office boasts Central Park views. Where Bloomberg proved a dispassionate technocrat, Trump is known to prize personal loyalty, operating his campaign with an unusually small, close-knit staff and handing big responsibilities to those he knows best, such as his children and long-time aides like Trump Organization chief operating officer Matt Calamari, whom he originally hired as a bodyguard after seeing him tackle hecklers at the 1981 U.S. Open.


Bloomberg: An outspoken supporter of gay marriage, abortion rights and gun control, Bloomberg was a lifelong Democrat until he ran as a Republican in order to bypass the highly parochial New York City Democratic party apparatus in the race to succeed Republican mayor Rudolph Giuliani on Jan. 1, 2002. He later abandoned the Republican party in 2007 and served his final years as mayor as an independent.

Trump: Like Bloomberg, the thrice-married, Planned Parenthood-supporting Trump has long held views that many consider socially liberal, making it difficult for some conservatives to embrace him as a true Republican. But many Republican voters, apparently more interested in his deeply conservative views on immigration and American exceptionalism, seem not to mind.

Relationship to Wall Street:

Bloomberg: Having made his fortune on Wall Street, Bloomberg was an unabashed champion of financial services and free markets (except when it comes to cigarettes and soda).

Trump: Some of his economic positions—such as opposing international trade agreements and calling out “hedge fund guys”—are notably populist and out of step with conventional Wall Street views.

Media savvy:

Bloomberg: While Bloomberg LP makes its money selling financial data to Wall Street, the company has also grown into a media empire, employing more than 2,000 journalists. Sometimes criticized for a fact-heavy style that places speed and directness over style, the organization won a Pulitzer Prize in 2015 for a series on how corporations evade U.S. taxes.

Trump: With unforgettable headlines (“The Best Sex I’ve Ever Had”) and a ubiquitous nickname (The Donald), Trump has been a fixture of New York’s fiercely competitive, in-your-face tabloid news culture for a generation, even surreptitiously acting as his own spokesman. As that no-holds-barred style spread first to reality television (“You’re Fired!”) then to forums like Twitter (“Sad!”), his skills and brashness have helped him outmaneuver more traditional rivals, leading him to the brink of national office.

Relationship with the Little Guy:

Bloomberg: While NYC voters elected him three times in a row, Michael Bloomberg can on occasion appear to place himself above the crowd. There was the time he disappeared from the city during a snowstorm on Christmas 2010. (Bloomberg notoriously refused to make his out-of-office whereabouts public while mayor, but in this case his private jet was spotted in Bermuda.) He also won his third term after overturning a term-limits law that was supposed to cap his tenure at two. Then, of course, there is New York City itself. While the city has undoubtedly thrived in the past fifteen years, critics note that it has also become increasingly divided between the fabulously wealthy haves and everyone else.

Trump: Despite his opulent lifestyle, Trump has managed to win millions of admirers by presenting himself as a sort of gold-plaited Everyman who tells it like it is, bucks political correctness, and is unabashed in his adolescent appreciation of the opposite sex. While populist economic stances are certainly one aspect of his Joe Six-pack bona fides, so too are helicopter rides.