Donald Trump

New York’s deep field of potential presidential candidates in 2020

It might be another New Yorker v New Yorker contest.

donald trump

donald trump Shealah Craighead / Official White House Photo

With the midterms behind them, presidential hopefuls across the country are gearing up for 2020, a race which some consider an open field for Democrats and Republicans alike. With names new and old being tossed around as possible candidates, one thing is clear: A large contingent of potential contenders hail from New York.

New York politicians have a habit of setting their sights on the presidency, establishing a well-traveled path of Empire State also-rans. The long list of past candidates includes Gov. Thomas Dewey, Gov. and Vice-President Nelson Rockefeller, Gov. George Pataki, Mayor John Lindsay, Mayor Rudy Giuliani, Rep. Shirley Chisholm and U.S. Sen. Robert F. Kennedy. Some, like Dewey, came agonizingly close to winning the White House. Former U.S. Sen. and Secretary of State Hillary Clinton did so twice, in 2008 and 2016. Other frequently mentioned political players, like former Mayor Michael Bloomberg and former Gov. Mario Cuomo, have publicly contemplated running before deciding to stay out.

Now, with one New Yorker in the White House who is planning to run for re-election and every New Yorker with a hint of national name recognition (other than U.S. Senate Minority Leader Charles Schumer) lining up to run against him, it looks like the next presidential election could be another intra-New York brawl.

Below is a guide to the possibilities. (Honorable mention goes to U.S. Sen. Bernie Sanders of Vermont, whose native Brooklyn accent shows he’ll always be a New Yorker at heart.) Of course, the chances each of these potential candidates has of winning is another question altogether.

Donald Trump

Chance of running: 95 percent


President Donald Trump is the first native New Yorker to take the White House in over 70 years (the last one was Franklin Delano Roosevelt). He’s almost certain to run again in 2020, having already raised more than $100 million since January 2017 and laid groundwork in key swing states while stumping for Republicans ahead of the midterm election. 

Still, the incumbent president may face a tougher re-election campaign than usual, as many have speculated that the chance of Republicans waging a primary challenge are high. While some potential contenders like U.S. Sen. Jeff Flake have already denied rumors about jumping in the race, moderates agree that a primary challenge is necessary, and U.S. Sen. Ben Sasse and Ohio Gov. John Kasich are frequently floated as ones who could level such a challenge.

The president also has low approval ratings, scandals surrounding his conflicts of interest and alleged history of tax evasion, and an ongoing investigation into his possible collusion with Russia to influence the 2016 election.

Robert Erikson, a professor of political science at Columbia University, argued that therefore there is a chance of Trump bowing out. “I think if he saw himself as possibly about to get humiliated in an election, he might decide not to run,” Erikson said. “Of course, there's always the chance of impeachment, which may not be high but it's above zero.”

Kirsten Gillibrand

Chance of running: 80 percent

US Sen. Kirsten Gillibrand.
William Alatriste for the New York City Council

In the field of potential Democratic challengers, U.S. Sen. Kirsten Gillibrand is one of the most frequently mentioned New Yorkers. Gillibrand stands apart from other Democrats in that her positions on issues like gun control and sanctuary cities have evolved – some might say “flip-flopped” – since she went from representing a conservative district in upstate New York to taking over Hillary Clinton’s former Senate seat. Gillibrand used to have an “A” rating from the National Rifle Association and was opposed to sanctuary cities. Now, she is an outspoken progressive, leading on women’s issues, and a supporter of gun control and immigrants’ rights.

Perhaps most significantly, Gillibrand is one of the few potential 2020 candidates who has admitted that she’s seriously considering running. In a reversal of her statement during her re-election campaign this year that she would serve out her six-year term if re-elected, Gillibrand said during a post-election appearance on "The Late Show with Stephen Colbert": “I believe right now that every one of us should figure out how we can do whatever we can with our time, with our talents to restore that moral decency, that moral compass, that truth of who we are as Americans. I will promise you, I will give it a long, hard thought of consideration. I will do that.”

Andrew Cuomo

Chance of running: 55 percent

Gov. Andrew Cuomo makes an announcement at the Association for a Better New York breakfast on April 5, 2018.
Don Pollard/Office of the Governor

Gov. Andrew Cuomo just won a third term by a wide margin. Judging by historical standards, that alone makes him a plausible candidate. And then there’s the widely held opinion that Cuomo has always had his eye on the White House, and that his relentless commitment to restraining taxes and spending was a product of his belief in Bill Clinton’s model of how a Democrat can win the presidency. Like Gillibrand, he promised during the 2018 campaign that he would serve out his full term. But reports of Cuomo reaching out to Iowa Democrats this week have reignited rumors that the governor is eyeing higher office. Cuomo has clearly tried to realign his political persona with the defiant attitude among the Democratic base, moving to the left a bit in his second term and campaigning heavily this year on his opposition to Trump. (His election night victory speech read like a practice run for his stump speech in New Hampshire next winter.)

Michael Bloomberg

Chance of running: 50 percent

Former New York City Mayor Michael Bloomberg.

Former New York City Mayor Michael Bloomberg is the perpetual almost-candidate – rumors of his candidacy have been floated in each of the past three presidential elections. And since ditching his status as an independent to register as a Democrat this October, it seems more and more likely that Bloomberg is fashioning himself as the candidate that both moderates on the right and the left have been waiting for. Bloomberg’s massive donation to Johns Hopkins University to support financial aid, coupled with an explanatory op-ed in The New York Times, seems like a well-timed bid for positive publicity.

“This could be different,” Erikson said, comparing this potential run to past ones. “To win, he could emerge out of chaos, or something like that. It's an interesting possibility, but I don't see it right now."

Some might argue that Bloomberg, at age 76, has waited too long and missed his shot. But being in or near their eighth decade didn’t stop Trump, Sanders or Clinton from running last time, and it might not stop contenders such as former Vice-President Joe Biden in 2020.

Bloomberg told the Times in September that if he were to run for president, he’d have to run as a Democrat, given how wide the gulf is between the former Republican and the GOP of 2018. So when he rejoined the Democratic Party this fall, ears understandably perked up, waiting to hear his intention to run. Those people will have to wait a little longer, as Bloomberg told The Associated Press that he would be sitting down to make the decision with his advisors over the holidays and announcing some time after that. “I think January, February would be about as late as you can do it and as early as you can gather enough information,” he said. “I think I know why I would want to run. I think I know what I think this country should do and what I would do. But I just don’t know whether it’s possible.”

Bill de Blasio

Chance of running: 20 percent

Bill de Blasio
Michael Appleton:Mayoral Photography Office

No one doubts that New York City Mayor Bill de Blasio would like to be president one day. He has spent an extraordinary amount of time, money and energy – the city’s as well his personally – promoting liberal causes and candidates all over the country and trying to raise his national profile. Like Cuomo, de Blasio has insisted he’s focused on his current office, but he hasn’t ruled out the possibility of aiming higher one day, saying that he wants to “continue in elected office if there is an opportunity to do so.” As far as potential candidates go, de Blasio isn’t a name that’s tossed around as frequently as someone like Gillibrand and Cuomo, but being mayor of the nation’s largest city – and one who can brag of crime going down, amid accomplishments like launching universal pre-K – is a plausible platform on which to run. Some have pegged him as the kind of dull candidate voters might counterintuitively value after four years of a chaotic Trump presidency. In that lane, he’d be competing with Bloomberg.

But whereas Bloomberg is a centrist from Wall Street, de Blasio has positioned himself as a leader of the Democratic Party’s left wing. Therefore, he’s unlikely to get in the race if Sanders runs again or if U.S. Sen. Elizabeth Warren of Massachusetts appears to have that vote sewn up. It’s possible de Blasio is setting himself up for a run another four or eight years beyond 2020. (At 57, he has a number of potential campaign cycles ahead of him.)

But even if de Blasio does want to run, his prospects may not be great. “There might be ambition, but I don't think there's much chance,” Erikson said, citing more exciting left-wing candidates such as Sanders - and de Blasio’s lack of popularity.

Hillary Clinton

Chance of running: 30 percent

mark reinstein/Shutterstock

Despite the fact that many accepted that 2016 would be the end of the road for Hillary Clinton, the possibility of her running again in 2020 still makes headlines. She did, after all, win the national popular vote in 2016 and at least one poll has shown that if the election were held again she would win in a landslide. Earlier this month, former Clinton advisor Mark Penn told voters to get ready for “Hillary 4.0.” Penn made no reference to any source for his prediction that she would run again in 2020, and Penn – a centrist, corporatist pollster – is no longer an insider to Clinton’s camp or the Democratic Party.

“I don't think she would run, and if she ran, I don't think she would have any traction,” Erikson said. “Her time has passed.”

But to be fair, Clinton herself hasn’t exactly ruled it out. In an interview with Recode’s Kara Swisher in October, Clinton admitted, “I’d like to be president.”

Though we don’t yet know just who will make up the field of candidates in 2020, there’s a good chance the next president will come from New York – whether that means four more years of Trump or a successful challenge by one of the candidates above. With no clear front runners, however, there’s always a possibility that even more candidates will throw their names in the hat. When it comes to New Yorkers and presidential politics, stranger things have happened.