Michael Bloomberg for President? Experts Weigh in on How He Could Succeed in 2020

Former mayor of New York City Michael Bloomberg.

Former mayor of New York City Michael Bloomberg. Andrew Burton/Getty Images

Last Wednesday, former New York City Mayor Michael Bloomberg posted on Instagram a picture of him filling out a New York State voter registration form, indicating that he was, after a 17-year hiatus, intent on rejoining the ranks of the Democratic party.

“Today, I have re-registered as a Democrat—I had been a member for most of my life—because we need Democrats to provide the checks and balance our nation so badly needs,” he wrote.

The social media post instantly provoked a flurry of headlines and chatter among the—now, thanks to Bloomberg—smoke-free backrooms of political clubs and newsrooms up and down the Acela Corridor, all trying to somehow divine the answer to the same quadrennial question: Is Michael Bloomberg finally going to run for president?

Subscribe to Observer’s Politics Newsletter

“The move is classic Mike Bloomberg,” said longtime political strategist Bradley Honan who has worked for Bloomberg, as well as both Bill and Hillary Clinton, Tony Blair and others high-profile names over the years. “At this point, he is just opening doors and creating options. You will know he is serious if we get wind of a spate of early morning breakfasts and power lunches with people like Claire McCaskill, Kamala Harris or Julian Castro—potential running mates he would need to cinch the Democratic primary in 2020.”

Bloomberg certainly has the financial wherewithal to upend the 2020 elections.

Although his 12-year track record running America’s most complex and challenging city would provide ample fodder for political rivals looking to make political hits, Forbes just listed the former mayor as the 10th wealthiest American, with a net worth just shy of $52 billion; Bloomberg writing a $1 billion check to his own campaign on the day he announced his candidacy would be tantamount to a deafening thunderclap, drowning out anything but the most salacious of claims by his Democratic rivals.

Yet despite his overwhelming financial advantage, a Jewish septuagenarian divorcé from New York City is probably not the princely Trump-slayer that most progressives have been envisioning as their standard bearer in 2020. To get through the Democratic primary, Bloomberg will need help from a running mate who can appeal to non-coastal voters who might not immediately see much of a difference between the former mayor and the billionaire president he would be vying to replace. Bloomberg will have to choose his VP wisely—and earlier than typical presidential candidates, who usually wait until they have sewn up the nomination to make their pick for vice president known.

I canvassed several leading political pundits from across the country to get their thoughts on the ideal pairing for an eventual Bloomberg presidential ticket. The results were a bit surprising.

Veteran political consultant Hank Sheinkopf thinks that Bloomberg, who only recently came back into the Democratic fold, will need to drape himself in party royalty.

“I think he would be wise to pick Caroline Kennedy,” said the New York-based strategist who has advised on multiple high-profile political campaigns, including past Bloomberg races. “The Kennedy name is still the gold standard in the Democratic Party, and nothing would inoculate Bloomberg more from progressive critics than having JFK’s daughter on the ticket.”

Darin Broton, a Democratic political consultant who has worked in races across the Midwest, thinks that Bloomberg would have to choose a woman from the heartland.

“It’s inconceivable to me that there will not be a woman on the Democratic ticket in 2020,” explained Broton. “And Bloomberg will need a veep who authentically represents the Midwest or the Rust Belt. If he is serious about running, I think it would behoove him to take a close look at Illinois Senator Tammy Duckworth, Missouri Senator Claire McCaskill or North Dakota Senator Heidi Heitkamp—even if some of these come up short in close re-election races this November.”

For Fox News political commentator and West Coast radio talk show host Ethan Bearman, there is one obvious choice for Bloomberg: “Julian Castro will not only give Mike a chance to put Texas into play, but it will light a fire among Latinos, who have never been represented on a major party presidential ticket. It would be historic.” 

“Julian was already on Hillary’s short list for VP so he has been vetted and accepted by the party stalwarts,” mused Bearman. “He has federal government experience. He even has a twin brother for goodness sakes—it’s like getting two for one!”

Yet despite Bearman’s enthusiasm for Castro, the idea of having a female running-mate was a consistent theme among most of the experts I canvassed.

Some might think that it is too soon to start speculating about potential running-mates for a candidate who hasn’t yet declared for a race that is more than two years out. But nearly all the pundits surveyed agreed that Bloomberg—should he pull the trigger this time around—would be wise to start early, especially given that Trump has effectively already begun campaigning for 2020. They reason that Bloomberg needs to maximize the leverage that his enormous cash advantage would give him, enabling him to get out his message early and unfettered by fellow Democratic challengers.

Bill Hillsman, the legendary political ad man who has worked with Independents and Democrats, thinks that Cecile Richards, daughter of former Texas Governor Ann Richards, would provide an effective counter-balance on Bloomberg’s ticket.

“Cecile has impeccable bona fides among Democrats,” remarked Hillsman of the former Planned Parenthood president. “Her mother Ann was a beloved figure in Texas and is national old-school Democratic politics. Richards appeals to women, both in the primary and the general elections, and helps Bloomberg make an impressive case to women voters, Democrats and progressives. In the era of #MeToo, she’s exactly the kind of VP Mike Bloomberg would need to win a crowded Democratic primary— if she’d agree to do it.”  

And in that scenario, the sooner Bloomberg picks a vice president, the quicker he would be able to placate the more progressive wings of his newly adopted party, lock up the nomination and set his sights on Donald Trump.

Of course, for now, Bloomberg has merely switched his party affiliation, but it’s a move that comes on the heels of his having pledged at least $100 million in support for Democrats running in House and Senate races.

It’s an amount that will buy him quite a few political chits, should he ever have a need or reason to cash them in some day.

Michael Bloomberg for President? Experts Weigh in on How He Could Succeed in 2020