Andrew Cuomo Could Beat Trump … If He Can Win Over the Left First

NEW YORK — The scene is unfolding in the shabby headquarters of the Hotel Trades Council just off Times Square in the late spring of 2017, but it’s not hard to imagine the speech somewhere in the Rust Belt in 2020, with a Democratic nominee trying to reclaim the Upper Midwest for his party.

“The truth is the middle class is under attack. The working families are under attack,” Andrew Cuomo bellows, his tough-guy accent coming in a little thick. “Middle-class wages are behind where they were 20 years ago. Think about it. All the pundits on TV say, ‘We don’t understand why there is such anger and anxiety.’”

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Standing before a crowd of unionized hotel workers several hundred strong, the governor of New York rails against Republicans for feeding workers like them a lie all these years. He speaks to them like he alone understands what they have been going through, watching wages disappear while the rest of the country gets richer. “It’s the labor movement that built the middle class and it’s the labor movement that’s going to have to rebuild the middle class in this country,” he thunders. He has the room, completely.

Cuomo is a big-name politician who has long seemed an extremely unlikely national candidate — until now, when suddenly he’s seeming like a very likely one. In theory, he is here to ceremonially sign a bill that would allow union members to deduct their union dues from their state taxes, but it’s clear what he is really doing today is waging a bigger argument against President Donald Trump.

“You want to deport immigrants? I say to them, start with me, Andrew Cuomo, the grandson of Andrea and Immacolata Cuomo, Italian poor immigrants,” he tells a roomful of people who are mostly immigrants.
The hotel workers stand up. They cheer. “Andrew Cuomo for president!” Someone yells. And then all at once. “2020! 2020!”

Cuomo stops. He wags a finger in mock annoyance, a broad smile across his face. “Don’t start trouble for me today. You are supposed to be my friends. This is not helpful.”

New Yorkers love to assume that their politicians are national figures by default, even as one by one they flame out on the big stage. For much of his career, Cuomo has looked like another in this long line: someone too nakedly ambitious, too pushy, with too messy of a personal life—too, well, New Yorky—to play much beyond Buffalo and the Battery. But suddenly it seems that Americans are willing to pull the lever for a muscular, messy, rough-edged leader shouting for the common man, and suddenly the governor is starting to show up on a lot of people’s lists.

“Look at his career, look at his work in New York,” said Jonathan Cowan, president and founder of Third Way, a centrist think tank, and a former Cuomo adviser. “He is laying out a model for what it means to be a 21st-century Democrat. Our party is in a deep hole. You have to look around and say, ‘Who is succeeding? Who is doing it differently?’”

It’s not just Democrats who see Cuomo showing up on the radar. “I would say Cuomo is the one I am most nervous about,” said Michael Caputo, a longtime adviser to Trump who helped put together an aborted Trump gubernatorial run against Cuomo in 2014, and helped lead the campaign for Carl Paladino, Cuomo’s 2010 Republican opponent. “Hillary Clinton wouldn’t take the gloves off. There isn’t a counterpunch Andrew Cuomo won’t throw.”

So far, Cuomo’s forays onto the national stage have been far more muted than some of the other talked-about potential 2020 Democratic nominees. There has been no book tour, no earnest Facebook videos or airport protest bullhorn photo-ops, no whispers that he is even thinking about it—although longtime friends and advisers have gingerly begun to bring it up to him. (They say Cuomo seems intrigued, but noncommittal.) In the world of political betting, most oddsmakers have him in the top 10, but barely.

Subtly, however, Cuomo looks very much like someone doing the spadework to run for president. His speeches, like the one at the Hotel Trades Council headquarters, are increasingly laced with the kind of big themes that become the rhetorical cornerstones of presidential campaigns. He rails against Washington, contrasting the gridlock of Congress against his own relatively smooth management of the previously dysfunctional Statehouse, the misplaced priorities of national Republicans against the steady progress he has made in Albany. Over the past several months, Cuomo has hired Chris Christie’s former chief of staff, a move widely seen as further burnishing his own bipartisan credentials; his aides have reached out to out-of-state donors about a possible fundraising swing later this year.

But if he runs, he’s got one big roadblock in his way first: The energy in the Democratic Party right now comes from a newly energized left. And the energized left, not to put too fine a point on it, hates Cuomo.

“The worst of the worst,” said Nomiki Konst, a Bernie Sanders delegate to the Democratic National Convention and frequent cable TV defender of the candidate who now serves on the Democratic National Committee’s Unity Commission. “Andrew Cuomo is somehow the only politician in America who still thinks neoliberalism and triangulation work, who opens up the Blue Dog playbook and says, ‘How can I use this to run for president?’”

Cuomo has in many ways solved New York, a state whose government routinely ranked among the most dysfunctional and corrupt in America. But if he hopes to be taken seriously as a standard-bearer, he has to solve something far more complicated: The Democratic Party, an institution that can make Albany seem like Sweden in its functionality. There are signs he’s already trying to work that puzzle: The state Democratic Party has run ads out-of-state featuring Cuomo alongside Sanders, trumpeting the Sanders-esque free college proposal that he pushed through. After six years of straddling the center line, can Cuomo convince his party’s progressive wing that he is actually one of them?


For most of Cuomo’s first six years in office, this was the kind of thing that couldn’t be talked about. Cuomo’s aides were on strict lockdown to never discuss it—not with the boss, and certainly not with reporters trying to catch him thinking about anything beyond the day-to-day running of New York. For years, Cuomo wouldn’t leave the state, even on vacation, as if just crossing the state line would trigger a cascade of “Is He or Isn’t He?” headlines. He even once declining to go to Washington to lobby for disaster relief funds after Hurricane Sandy. “If I went to Washington now,” Cuomo asked reporters at the time, “what story would you write?”

It’s a vintage Cuomo comment, one that speaks not only to his ruthlessness and ambition, but his awareness of how that ruthlessness and ambition are viewed. (Needless to say, he declined to be interviewed for this article about his presidential prospects.) Cuomo was a top political aide to a father who famously dithered in his own presidential exploratory foray, and the son was determined to not get sidetracked by similar whispers. He was aware of his reputation; if Mario was the American Cicero, Andrew was the Dark Knight, his father’s relentless political enforcer. Mario wanted to appeal to the better angels of our nature; Andrew would spear all the bad angels and step over the bodies on the way to higher office.

Cuomo is a kind of Northeastern political royalty—the son of a governor, once married to Bobby Kennedy’s daughter. But his ascent to the Statehouse did not come without a fight. After a stint as Bill Clinton’s secretary of Housing and Urban Development, and with his marriage to Kerry Kennedy collapsing, Cuomo cut the line and embarked on an ill-fated run for governor of New York, even as the state’s Democratic establishment was firmly behind state comptroller Carl McCall, who would have been New York’s first African-American governor. Cuomo compounded the problem by dropping out just before the primary, denying McCall the chance to fully trounce him.

Single, alone in the political wilderness, Cuomo assiduously worked his way back, working on homelessness and rallying with the likes of Russell Simmons and other hip-hop stars to reform the state’s punitive Rockefeller Drug Laws. He won election as attorney general despite resistance from the New York Times editorial board and other left-leaning institutions, and then ran the only two people ahead of him in line—Gov. Eliot Spitzer (with an assist from Client 9 on that one) and Lt. Gov. David Paterson—out of town on a rail.

But he had a perception problem: To New Yorkers who knew anything about him, which was most New Yorkers, Cuomo was political ambition personified. Would he stay governor, or just step over the bodies once more on his way to something else? So he made it his mission to neutralize that attack. He made it known that serving as governor of New York was the highest pinnacle a Cuomo could ever hope to achieve. Former aides say that any mention of higher office during planning meetings in the first years of his administration would have brought quizzical looks, as if they had interrupted a strategy session to talk about your favorite TV shows.

“Everyone thought he was running for president,” said one former aide. “So he decided he would relentlessly communicate that he was focused on running the state.”

When he at last became the second Cuomo to serve as governor of New York, by the standards of the state, he was barely a Democrat. It was in the depths of the Tea Party’s counter-revolt against Barack Obama’s presidency; the state’s economic outlook was disastrous and Cuomo positioned himself firmly as a man of the center. He capped property taxes and let a tax on millionaires expire. He gathered a bunch of friends in the real estate industry to run an outside spending campaign on behalf of his agenda, rallied for charter schools, slashed pensions and the state workforce. If Spitzer had come to Albany as a crusader, cleaning out the ethically compromised and ridding the state of the Republicans who could slow his agenda, Cuomo signaled from the start that he was willing to work with the powers that be, so long as their powers didn’t get in his way. In 2011, when a group of moderate Democrats announced they were leaving their party’s conference in the state Senate to form an alliance with the Republicans, Cuomo signaled his tacit approval, in part because it meant that his veto pen wasn’t the only thing keeping restive downstate liberals from having the run of the state. He undercut liberal stalwarts like Attorney General Eric Schneiderman and New York Mayor Bill de Blasio, trying to incorporate parts of their offices’ responsibilities into his own, and leaking gossipy and embarrassing details about them to the press.

In the era of Occupy Wall Street, such machinations made Cuomo Democratic Public Enemy No. 1. On MSNBC, Chris Hayes called Cuomo’s power play against a Democratic Senate, “a remarkable cynical display.” “Andrew Cuomo, Fake Democrat,” blared Salon. Over at Daily Kos, Markos Moulitsas delivered the death blow, comparing Cuomo to—gasp!—Joe Lieberman. In an era in which moderates were supposed to find no safe harbor save for a couple of hideouts in the Mountain West, Cuomo remained defiantly in the middle, practically delighting in how much he could troll his lefty detractors.

But in 2014, something changed: A little-known, poorly funded Constitutional law professor named Zephyr Teachout ran against Cuomo in the Democratic primary and captured a third of the vote, proof that not only was a restive progressivism already brewing in the pre-Trump, pre-Sanders era, but that the party’s liberals didn’t care much for their governor. Cuomo responded by swinging abruptly to the left. Since then, even with the state Senate’s hybrid Democratic-Republican coalition still in place, Cuomo has passed a $15 minimum wage, implemented a robust paid family leave program, raised the age of criminal responsibility to 18, rushed through a plan to make tuition free at the state’s public colleges and universities, and banned fracking.

Progressives see a cynical exercise in box-checking. Cuomo’s advisers see someone moving at the pace of the people he was elected to represent, and point out that liberals are naive if they think the conservative forces, even in this blue state, from financial titans to the vast stretches of the Rust Belt upstate, can be steamrolled. Cuomo, they say, was a progressive presiding over a broke and broken state for his first term, and still managed to legalize same-sex marriage, pass some of the strictest gun laws in the nation and embark on an infrastructure rebuilding project unseen since the days of Robert Moses. The most jaded Albany observers see a competitor constantly trying to own the game. “We know we are all just pieces on a chessboard to Andrew. He views purely from a standpoint of what he can get from us,” said one longtime capitol political operative, who like most of them has known Cuomo for decades. “The standing joke among a lot of us is that we hope we aren’t just pawns at this point—that we’re at least rooks or knights in his game.”


If Andrew Cuomo has a problem on his left flank, it isn’t just because he doesn’t always toe the party line; it is far more personal than that. To them, Cuomo is fundamentally dishonest, a political weather vane obsessed with his own ambition. To him, they are soft-headed naifs who don’t understand how politics works and don’t speak for the millions of workers and labor unionists who serve as the real base of the Democratic Party.

At times, Cuomo’s moves on his leftward rivals have been so aggressive that it seems he takes a kind of delight in foiling them. Consider his interactions with the Working Families Party, a homegrown New York third party of unions and liberal groups that, because of the state’s unique fusion voting system, has become an electoral powerhouse over the past decade. Back in 2014, the party was riding high after getting behind de Blasio’s mayoral campaign and lending its endorsement to a substantial bloc of winning candidates on the New York City Council. They seemingly had Cuomo at their mercy. A sizable portion of their membership wanted to give their endorsement to Teachout. The WFP gets its own line in a prime place on a New York state ballot, and if they’d put another candidate on it, that would have siphoned away significant votes from Cuomo in the general. But party leaders, led by de Blasio, worked members to give their line to Cuomo. In exchange, Cuomo agreed to address the WFP convention and to commit to helping Democrats take over the state Senate, and promised to push for a rash of progressive agenda items.

Instead, after he won the line, Cuomo addressed the convention only by video; created his own party, the Women’s Equality Party, which drained votes from the WFP; welshed on his promise to campaign for Democrats; started an all-out war with de Blasio; and swung to the left while cutting the WFP out of any future rallies and bill-signings even as he pushed priorities they had spent years building support to achieve.

To Cuomo, this was less a matter of ideology than tactics: “This is politics in New York,” said one adviser. “You’ve seen ‘Animal Planet’? You have problems, and you neutralize them. Occasionally, you have to remind everybody who the top dog is.”

This kind of attitude doesn’t go unnoticed, though. There is hardly any big player in New York state who hasn’t faced Cuomo’s wrath. Around the Cuomo administration, state comptroller Tom DiNapoli was called “Chipmunk Balls,” for his unwillingness to combat spendthrift lawmakers, according to anonymous leaks in the tabloids. The governor has been known to ask people whether Schneiderman, a political rival, wears eyeliner (he doesn’t, but he does take a glaucoma medication that makes his lashes thicker). He seems to delight in torturing de Blasio.

Throughout New York state politics, it is hard to find anyone who doesn’t work for him who has warm feelings toward the governor. “It’s not enough for him to win,” said one prominent Democrat. “You have to lose.”

“Sometimes I think there is something mentally wrong with him,” said a former aide to another official who faced Cuomo’s wrath. “I never known anyone who was so obsessed with fighting all the time.”

Politicians in and around Albany say that if they cross Cuomo, even a stray quote in the newspaper, they can expect an almost immediate spittle-flicked phone call from his office. “Honestly, you just start to give up after a while,” said one.

Albany is full of stories of Cuomo pulling on strings that no one else knew even existed. When he first became governor, he quickly formed an alliance with Fred Dicker, a hugely influential conservative New York Post columnist and talk-radio host who helped hound Spitzer and Paterson from office. Cuomo would appear regularly for friendly chats on Dicker’s radio show while “sources close to the governor” trotted out the administration’s line in his column. It was as if Barack Obama had become buddy-buddy with Rush Limbaugh. Pulling a powerful potential enemy to your side is a political triple axel if you can land it—but utterly infuriating to committed liberals (The arrangement eventually sputtered as Cuomo tacked left, and Dicker retired last year.)

Cuomo also kept the plates spinning on the ever more complicated state Legislature, where Republicans need the breakaway Democrats to pass legislation. Cuomo figured out how to use the arrangement as a foil when convenient (Can’t pass a statewide DREAM Act with those Republicans in charge, sorry!) but getting his way whenever he put his shoulder to the legislative wheel. He set up a commission to investigate public corruption and used it to get lawmakers to pass ethics reform, then abruptly shut it down when the commission turned its sights on the governor’s office. He passed marriage equality, something that stymied his predecessor, and wrested every dollar he could out of the deep-pocked LGBT community around the country along the way. He constantly calls labor leaders, and they deploy or withhold their get-out-the-vote firepower at the governor’s request, regardless of party. Even this year, when a number of lawmakers threatened to disrupt his annual State of the State address with protests over the governor’s refusal to go along with legislative pay raises, Cuomo didn’t plead with them or negotiate. He simply announced that there wouldn’t be a State of the State, that instead he would travel to their districts, hosting a series of speeches around New York. Show up or don’t, he all but dared them, but don’t box me in.

“Every time you think you have a run against him, he shuts it down. He is diabolical. And I don’t even mean that in a negative way. It’s like he’s a shark. He’s not happy unless he’s going in for the kill. He’s a purely political animal. I never seen anything like it,” said William F.B. O’Reilly, a top Republican political operative in New York who worked on the campaign of Rob Astorino, who ran against Cuomo in 2014. “I think he spends all night doing political diagrams in his head. Every time you think you have him in a corner you realize that he has already been on a scouting mission down that path and he has found the back door. And it happens time after time. It’s hard not to be in awe sometimes.”

Caputo, the former Trump adviser who helped prepare the real estate tycoon’s aborted run for governor in 2014, went digging for dirt on Cuomo in 2014 and 2010. Caputo is a close friend of GOP operative Roger Stone, and he was certain that there was enough on the governor to end his career, but despite the best efforts of him and his team of investigators, “every time you think you are getting close, you open up a door and you smell nothing but Lysol. I don’t know if he has skeletons in his past, but I can tell you he has completely cleaned them up if he does.”

“You can’t get a direct hit on Andrew Cuomo,” Caputo added. “He’s already thought of what you are going to hit him on. … And he’s monomaniacal. If he wants something, if he wants the presidency, God forbid you stand in his way. I don’t care what party you are from.”


Which is why, for all of the angst Andrew Cuomo brings up among some sections of the Democratic Party, he might be precisely the kind of character the party needs to take on Donald Trump. Trump changed the game of politics, made it coarser, less concerned with what were thought to be bedrock American political principles; he has a unique ability to steer himself straight into disastrous conflict and then punch his way out of it. Alone among the 2020 contenders, Cuomo looks like someone who would be undeterred by whatever gold-rimmed kitchen sink Trump throws. With vanishingly few exceptions, he has outmaneuvered everyone in a state whose political class thinks it is more sophisticated than most. He has played nice when playing nice was called for, and disemboweled whoever stood in his way if the chance presented itself, racking up progressive victory after progressive victory in the process.

But will it be enough? For the party’s left flank, which in 2016 flocked to the side of a 70-something Brooklyn socialist, winning isn’t even the point. Politics is about showing where you stand, and bleeding on the cross if need be.

“In the Age of Trump there are millions of people living in actual fear of what is going on in this country,” said Bill Lipton, the New York director of the Working Families Party, “and they want to see politicians base their actions on a set of deeply held shared values.”

To Lipton and many on the left in New York, Cuomo isn’t a force for progressive change but a hindrance to it. After all, if he seems to be able to move an agenda almost at will, why can’t he steamroll the state Senate’s weird internal politics and give New York City liberals the run of the state?

A few weeks ago, a group calling itself Rise and Resist staged a rally in front of Cuomo’s Manhattan office calling on the governor to push for a Democratic-controlled Senate. Claire Ullman, one of the group’s spokespeople told me that, “By keeping the Senate in Republican hands, really progressive legislation comes out of the Assembly, but doesn’t make it to the Senate floor. He benefits by not having to sign a lot of progressive legislation, which allows him to appear moderate to the rest of the country as he revs up his presidential ambitions.”

As an oversized puppet of Cuomo dressed as an undertaker with dollar bills stuck to his cloak danced behind her, I asked whether Ullman would support a Cuomo presidency, given that she was here protesting his governorship.

“I have mixed feelings about him,” she replied. “He has done some really good things, he really has. I think his resolve is tempered by his ambition, but he comes out on the right side on issues. But it’s like any politician—it’s partly strategy and self-interest, and it’s partly conviction.”

After Trump was elected, Cuomo at first took a moderate line. “I look forward to working together with him,” Cuomo told a local cable host the day after the election, comparing it to his own record of working with the Republicans who control the upper house of the state Legislature, predicting that the kind of hostility that New York governors were used to hearing from Republican presidents would be absent from this one. “He understands some Queens, he knows New York,” he said. “I think Donald Trump being from New York is a bonus not just for this state, but for other states also.”

He soon figured it out, though: In the Age of Trump, the party expected nothing short of war. Cuomo, being Cuomo, couldn’t help but go a little overboard. He unveiled that riff about how if Trump starts deporting immigrants, he should start with him, even though the Cuomos have now been on these shores for a couple of generations. He visited the Union Square subway station that New Yorkers had turned into a “Therapy Subway Wall” of colorful anti-Trump Post-It notes, quoted the Emma Lazarus poem from the Statue of Liberty and signed his Post-It, “Andrew C.”

Cuomo still scarcely calls out Trump by name, fearful of finding the federal spigot turned off for some of the infrastructure projects that he has depended on. But otherwise, Cuomo—a governor who enabled Republicans to remain in power and openly tangled with his own party’s brightest lights—is clearly trying on the garb of a full-fledged member of #TheResistance. Just in the past month, he announced that he would ban any insurer that dropped out of the Obamacare market from participating in the state’s Medicaid program, announced that the state would join the Paris climate accord, and held a midtown rally alongside Nancy Pelosi and woke celebrities like John Leguizamo and Steve Buscemi to announce an all-out assault on the half-dozen or so New York congressional Republicans thought to be vulnerable in 2018.

He’s beginning to travel out of state, including serving as policy chair for the Democratic Governors Association. He responded to a series of anti-Semitic incidents around New York by jetting off to Israel. And he’s sharpened his language, too, contrasting Washington’s meanness with New York’s fight for justice.

“We’re talking about working together. We’re talking about legislative progress. They’re talking about partisan politics, they’re talking about gridlock, and they’re seeking to impose an ultraconservative philosophy which is repugnant to everything we believe in,” he said in May at an announcement that the state was going to embark upon a $20 billion plan to build more affordable housing and combat homelessness.

And then—“sounding like Friedrich Fucking Engels,” as one lefty operative who opposes Cuomo sniped to me later—he launched into an attack on free-market politics. “The gods of the private market are not our god. We don’t follow that god. And we believe when the private market fails, that we have a collective responsibility to help one another. … That’s society’s responsibility, and that’s what we do through a collective vehicle, and the collective vehicle is government.”


Is it genuine? Well, he genuinely wants the backing of people who think those things. It would be impossible to mount a presidential campaign in this day and age without a groundswell of support from the party’s liberal edge. People close to Cuomo know he needs to do some repair work in New York, end his bitter feud with de Blasio, push for a Democratic Legislature.

He knows they will never love him. Cuomo still sees himself as an outer-borough guy, his advisers say, as the kind of person whose favorite weekend hobby is working on old cars. Those mandarins at the New York Times editorial board or perusing Mother Jones in the checkout line of the Park Slope Food Co-Op who think politics is about pretty words and debating ideas will never get it. “He thinks the far left think they are so much smarter and more righteous than everyone else, and that if you don’t constantly kiss their ass that there is something repugnant about you,” said one adviser. “He really doesn’t care. He’s got the unions on his side, and he knows that’s worth more than whatever the 800 ivory tower liberals in New York think about him.”

Liberals will never love him, or even learn to see him as one of them. But it’s clear that Cuomo can move an agenda forward. If he delivers on progressive priorities, can they learn to live with him? As friends and advisers of the governor see it, Cuomo enters the discussion of top-tier presidential contenders in a party that hasn’t just gotten used to symbolic victories; it has become comfortable with even symbolic losses. Consider climate change, or health care, or taxes, or for that matter, the way Democrats slunk back to their hideaways after winning the popular vote but losing thanks to an arcane scoring system from the 18th century.

Progressives comfort themselves with clichés now as vapid as they are well-worn—putting points on the board, moving the needle, bending the arc—and rest content that since they have facts and morality on their side, things are bound to go their way eventually.

Crack open Andrew Cuomo, and you won’t find Ted Kennedy. You probably won’t even find Mario Cuomo, someone who treated Albany like it was the Athenian agora. But you will find someone consumed with winning, who throttles anyone who looks like he or she might stand in the way of that winning. Is Cuomo really a warrior for social justice? Maybe, but probably not, but if you get a higher minimum wage and paid family leave and free college and same-sex marriage and gun control and a fracking ban and the first reversal of harsh Rockefeller-era drug laws in four decades, who cares?

“I’ll just be brazen and say it. If he decides to run for president, he’d be a really good president,” said Ken Sunshine, a public relations consultant for A-list celebrities and a longtime adviser to both Cuomos. “Yes, Andrew doesn’t come from lefty intellectual circles. Fine. But I defy anyone to make a substantive argument that Cuomo isn’t a progressive. The fact that we keep having these over-intellectualized arguments is why we keep losing to morons. I’ll put my progressive credentials against anybody, but I tell you something: I like it when Democrats win. And the alternative is a catastrophe.”

David Freedlander writes about politics and culture. He lives in New York.

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