One brought his father’s real estate empire into Manhattan and turned it into a global brand. The other took his father’s political mantle and built a career in both Washington and New York, winning three governor’s elections of his own.
Both revel in finding weakness and needling those they don’t respect. Both can be abrasive, then charming a moment later. Both present themselves as forever underestimated. Both have faced a litany of scandals and been accused of sexual misconduct by multiple women in allegations they both deny and dismiss as politically motivated. Both have small circles of ultra-loyalists and much longer lists of enemies who want them to fail.
Now, seven months after Donald Trump won a second White House term that he presented as part vindication, part retribution, Andrew Cuomo is seeking his restoration.
Ahead of Tuesday’s Democratic primary for New York mayor, Cuomo has centered his bid on the idea that he alone has the stature and experience to fight Trump. Their lives have intersected and crashed into each other for 40 years – over politics and policy, literal questions of life and death during the Covid-19 pandemic, but also personality and self-assurance that each knows better what their parties, and Americans, want.
That worries some who have clashed with both.
“Seeing what I see from Washington, DC, which is only focused on retribution and revenge, there are a lot of similarities in certain people running for the mayor of the city of New York, and I don’t need those same characteristics to be revealed in the office of the mayor or the city,” said New York Attorney General Tish James, a longtime Cuomo and Trump critic.
For decades, they were competing Macy’s Thanksgiving Parade balloon-sized personalities who made the motions of friendship to get what they wanted.
Trump recorded a video played at Cuomo’s bachelor party, warning him not to cheat. Nineteen years later, Cuomo was one of the guests watching Trump walk his daughter Ivanka down the aisle at her wedding to Jared Kushner. Over that time, Trump donated a total of $64,000 to Cuomo’s campaigns.
A few days after Cuomo won his third term as governor in 2018, he flew to Washington to have lunch with Trump, where the president greeted him like an old friend. Before walking out of the Oval Office grabbed Cuomo’s arm and said, “Hey Andrew, can you believe this?”
The year that defined them both was 2020. As they faced off over immigration, Covid-19, racial justice protests, and federal funding for the state of New York, Cuomo would return to the Oval Office for what would be the first of three in-person meetings, along with dozens of phone calls and quite a few tweets.
A dozen aides to Trump and Cuomo revealed new details about those run-ins to CNN. They spoke on condition of anonymity to discuss private meetings. Those details may be the guide for what may be ahead if Cuomo becomes mayor and they inevitably meet again.
February 13, 2020: Immigration and international travel
The meeting started with a warm handshake, with the White House photographer right up close to get the smiles.
“You should sit here,” Trump said, pointing Cuomo to one of the chairs in front of the Resolute Desk, according to one person in the room.
That morning before heading to the White House, Cuomo had accused Trump of “extortion”: The president was threatening to revoke “trusted traveler” status for New York, which allowed for Global Entry speeding travelers through customs, if the governor didn’t give the administration access to the state’s driver’s license database. Immigrants without legal authorization can get licenses in New York. Cuomo didn’t want the database to be used for immigration raids, but he also didn’t want to lose all the international travel business.
In the meeting, Trump held up a sheet with three columns of states, arranged by color. All green were giving Trump all the information he wanted. Green and red were mixed. New York, Trump pointed out, was all red. He shoved the chart across the desk at Cuomo.
Trump name-checked a few rich New Yorkers who didn’t want to have their access to Global Entry shut down.
“It’s good leverage,” he pointed out to Cuomo, according to the person in the room.
“You can do this, but we will sue you,” Cuomo told him.
By the end, neither the president nor the governor had conceded anything, and aides to both thought they’d outmaneuvered and cornered the other. Trump slid a small stack of red MAGA hats toward Cuomo at the end, talking about his poll numbers and how great his re-election campaign was going to be. Cuomo glanced at them and did not pick them up.
Eventually, the administration produced a memorandum of understanding that did not admit doing anything wrong but did back off the threats. A court reinstated the “trusted traveler” later that year.
But within weeks, no one was traveling much at all.
April 20, 2020: Fights over Covid
Trump was on the phone quickly after the first confirmed coronavirus cases hit New York. He had been yelling at rallies that the virus was a Democratic hoax, but to Cuomo, he was asking what the state needed, what he could do to help.
Within days, their daily dueling briefings began. Cuomo liked the attention, the sudden nationalization that made him both a social media hero for locked-down liberals, driving Democratic speculation that he could sub in as the Democratic presidential nominee for a man already showing his age, then-former Vice President Joe Biden.
Cuomo and Trump watched each other on TV. They went in front of cameras to respond to mock and undermine each other. Then they got on the phone and blew past whatever had been part of the show to talk about what they were going to do.
Trump was giving Cuomo’s team access to statisticians and academics trying to figure out what was happening. Cuomo was grateful, often telling aides who were running into problems that he’d walk into his office and call the president directly to get them cleared, enjoying being able to bypass what he’d felt were too many steps in dealing with the previous administration of Democratic President Barack Obama.
When Trump toyed with blockading New York City, Cuomo wrote a New York Times op-ed with one reader in mind. Trump called him as soon as he saw it, and talk of a blockade stopped.
Cuomo felt like he was in the catbird’s seat, his aides say, of being in a crisis needing something out of a president he was convinced he knew how to work.
“They both understood why each of them was taking the public approach, and it didn’t bother them why the other one was saying what they were saying publicly,” a former state official told CNN.
Cuomo and a few aides were back in the Oval Office two weeks later to ask for more help. Each state was being allocated 20,000 tests per day, and Cuomo felt the severity in New York should get their allocation boosted to 40,000.
Going in, Cuomo had been amused that he and his aides had to test multiple times before seeing the president themselves.
Trump was behind the desk again, Cuomo and aides in chairs in front. According to three people in the room, the president kept the conversation loose, armed again with charts and a marker to make points. Trump asked Cuomo if he’d seen the “Bikers for Trump” rally that had just happened. He asked how Cuomo’s mother was doing. Cuomo sat back, letting him go on before interjecting to bring him back to a specific ask. He even brought the president a bottle of New York-branded hand sanitizer.
“They always did that charm dance with each other because they were Queens brawlers,” one Cuomo aide at the time told CNN.
Trump asked Cuomo how “our hospitals” back in Queens were doing. Eventually, he agreed to the extra tests, but not the extra disaster aid Cuomo wanted too. Trump offered to put Cuomo on the phone with the doctor who’d treated then-British Prime Minister Boris Johnson, who had just recovered from coronavirus.
On the way out, Cuomo and his retinue ran into Treasury Secretary Steven Mnuchin, according to two people who saw the interaction. Cuomo asked about the disaster relief money, and when he heard it wasn’t resolved, he brought them back into the Oval Office. Trump, already back in his private dining room watching TV, came back in and agreed to the request. As they left, he gave Cuomo a few extra rapid testing machines they had in the White House for his use.
Cuomo aides convinced themselves that they were being strung along so that Trump would cajole Cuomo to join his briefing that evening. Trump aides say that was never a possibility.
They each did their briefings after Cuomo returned to New York.
May 27, 2020: Infrastructure and social justice
Two days after George Floyd was killed, Cuomo was back in the Oval Office. He wanted to get Trump thinking that more federal money for infrastructure projects could “supercharge” the projects while giving Trump potential accomplishments for an ongoing re-election campaign that appealed to him personally and politically.
The meeting did not go well – Trump came in incensed that the New York attorney general had subpoenaed his children and was convinced that Cuomo had orchestrated it, according to top Cuomo aide Melissa DeRosa, who detailed the encounter in her book, “What’s Left Unsaid: My Life at the Center of Power, Politics & Crisis.”
But afterward, Cuomo went a few blocks over to the National Press Club in Washington and said it was a “good conversation.”
“The president is from New York, so he has a context for all these things we’re talking about,” Cuomo said.
The money never arrived.
They talked more when the summer of protests sparked by Floyd’s murder began to grow violent in New York. Though things were never as intense there as in other parts of the country, Cuomo responded with a stronger hand than his rival, then-Mayor Bill de Blasio, pushing de Blasio to establish a curfew, moving to send in state police, and openly considering sending in the National Guard himself.
A few weeks later, Trump was dangling the threat to send troops into more cities. Cuomo called him and told him not to. Trump told him to stop criticizing him publicly. Cuomo backed off. The troops never came.
The relationship dissolved again later that summer, when Trump was furious about Cuomo’s recorded speech to the Democratic National Convention. Far from the famous rallying keynote Mario Cuomo delivered against Ronald Reagan in 1984, it was still a call to action, and a call to kick out “a dysfunctional and incompetent” Trump. The president spent the night tweeting furiously about “the horrible governor.”
2025: A new face-off
Since Trump moved troops into Los Angeles two weeks ago to quell protests over immigration enforcement, Cuomo has repeatedly said that Trump didn’t do that when he was governor and wouldn’t do it if he were mayor. Trump aides question both claims, but Cuomo does have the 2020 parallel to point to.
Trump has made clear he wants the operations in Los Angeles to be the first in a series of moves into blue cities.
Cuomo has spent the closing weeks of his campaign leaning heavily into anti-Trump talk and warning about repeats of Los Angeles in TV ads, in mailed materials, and in comments on the trail. Last month, when word leaked that the Department of Justice was stepping up its investigation into him for possible perjury in congressional testimony over his handling of COVID-19, he linked himself to other Democratic politicians the president has targeted.
“We know Mr. Trump, because this is Trump II. I was there for Trump I,” Cuomo boasted on Thursday at a stop. “Don’t ever forget that we beat Trump once. We’re gonna beat him again.”
Cuomo’s opponents, meanwhile, have said he wouldn’t stand up enough, and “I think New Yorkers are hungry for a different kind of politics,” progressive challenger Zohran Mamdani began one campaign video, standing outside of Trump Tower, drawing comparisons between the two of them.
Incumbent Mayor Eric Adams, who is seeking reelection as an independent, and others say Cuomo is only running to line himself up for Trump’s current job in 2028.
Cuomo, in turn, says his rivals aren’t tough enough and recently suggested Trump would cut through Mamdani, a 33-year-old state assemblyman, “like a hot knife through butter.”
He argues repeatedly that his experience is a main reason to elect him.
The president was asked in April about Cuomo. Aboard Air Force One, Trump claimed credit for helping New York during the pandemic before offering an apt summary of their relationship.
“I’ve always gotten along with him,” Trump said. “We’ve had our ins and outs a little bit.”
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