But as Chera lay dying in recent days, Trump seemed genuinely affected by his friend’s plight, referring on several occasions to Chera’s rapid descent.

“My deepest sympathies go out to Frieda Chera and the family of the late, great, Stanley Chera, one of Manhattan’s most brilliant real estate minds,” Trump said in a tweeted condolence note to Chera’s family on Monday. “Stanley was charitable, kind, and a wonderful friend. He will be truly missed!”

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Trump calls a lot of people his friends, but he has said on several occasions that he doesn’t have close friends in the way most people use the term. Ever since he was a rich kid with a famous name growing up in Queens, Trump was wary of the kind of friendships he saw in the movies.

“I think I have a lot of friends,” Trump said in a 2016 interview with The Washington Post, “but they’re not friends like perhaps other people have friends, where they’re together all the time and they go out to dinner all the time.” He said he always had to wonder whether people wanted to be near him because of his money and power, and not out of genuine friendship.

On the surface, Chera and Trump seemed to have little in common beyond their wealth and line of work. Chera started out in New York’s outer boroughs and was happy to stay there, embedded in the city’s tightknit Syrian Jewish community; Trump had a burning need to get from Queens to Manhattan and never looked back after he made the move in his early 20s.

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Chera, who was 78, was a devoutly religious man who gave many millions to charities. Trump was never much of a churchgoer and often failed to fulfill promises to make large donations to good causes.

Despite their differences — Chera once said that his “secret is to stay underleveraged and you can own something forever,” a decidedly un-Trumpian approach — the two men shared a bond that the president has often lamented missing during his three years in Washington. It’s a New York thing, a camaraderie that stems from a common lingo, a brash attitude, a humor that can come off as cruel to people who didn’t grow up with that way of poking those you like as well as those you can’t stand.

“They had a closeness to them, President Trump and Chera,” said Anthony Scaramucci, a fellow New Yorker who did a historically brief stint as Trump’s director of communications in 2017. “In a very weird way, Trump is a bit of a loner. He flattens people very quickly. His relationships are more detached than most people’s. But with someone like Chera, he can connect because he grew up with these people.”

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According to three New Yorkers who have known Trump for decades, the president has lamented since arriving at the White House that many Washington politicians don’t get his humor, don’t even realize when he’s being serious and when he’s just mouthing off.

And Trump misses the rough and tumble of New York’s real estate business, where rivals may slam one another one day and make a huge deal together the next. “Most of my friendships are business-related,” he said in the 2016 interview, “because those are the only people I meet. . . . I have people that I haven’t spoken to in years, but I think they’re friends.”

Chera was one of a handful of prominent Syrian Jews who own many of the prime buildings and storefronts along Manhattan’s most storied avenue, which happens also to be where Trump built his most prized structure, Trump Tower.

“Trump never really fit in with the big families that control much of New York real estate,” said one of the top property owners, who spoke on the condition of anonymity to avoid jeopardizing his relationship with the president. “They didn’t really trust him, and they thought he was way too public. These are people who do not like to be in the papers, which Donald lives to do.”

Chera’s son Haim, who is in charge of retail at Vornado Realty Trust, called his father a “giant-hearted champion of the underprivileged.” He told the Real Deal, a New York real estate news site, that his father was a “captain of the team for the correct and just, not the popular.”

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Despite their reservations about him, Trump’s Fifth Avenue competitors kept him close and, like him, they played all sides of the game.

As Trump did for most of his career, Chera gave big money to politicians of both parties, often to whomever was in power. Chera’s family real estate firm, Crown Acquisitions, donated more than $20,000 to New York’s Democratic mayor, Bill de Blasio, through his Campaign for One New York in 2015. The next year, Chera gave $30,000 to super PACs backing then-N.J. Gov. Chris Christie (R) and $50,000 to the Trump Victory Committee.

Chera was an early and generous supporter of Trump’s presidential run. From 2016 through 2019, he and his wife gave more than $500,000 to support Trump’s campaigns, Federal Election Commission records show.

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Chera attended and organized early fundraisers for Trump. In the 2016 campaign, Chera was one of Trump’s eight New York finance chairs, a mostly honorary position handed out to big donors.

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“Chera and I organized a fundraiser for Trump in June [2016],” said Scaramucci, another of the New York finance chairs, “and we had a large room but only about a hundred people — it was still early.”

Scaramucci brought his mother to that event and sat her in the back of the room — “I was trying to fill some seats,” he said. “Stanley went over and moved my mother to the head table. He’s a remarkably classy guy.”

Although Trump did not see him often, Chera was evidently on the president’s mind in recent days. At a news briefing on March 30, Trump said: “I have some friends that are unbelievably sick. We thought they were going in for a mild stay. And, in one case, he’s unconscious — in a coma. And you say, ‘How did that happen?’ ”

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The president came back to Chera, without naming him, the next day too: “He’s sort of central casting for what we’re talking about, and it hit him very hard. I’ve never seen anything like it.”

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Chera had been closely involved in Trump’s reelection effort. During a March 2019 campaign rally in Grand Rapids, Mich., that Chera attended, Trump riffed about him to the crowd: “A friend of mine — he’s very shy, but he’s very rich. He shouldn’t be shy. He’s one of the biggest builders and real estate people in the world. . . . Stanley, those big beautiful buildings in Manhattan. You know those beautiful buildings — he owns them. Stanley, how much did you make this month?”

Beyond their bond as Fifth Avenue property owners, Chera and Trump were connected through the president’s son-in-law, Jared Kushner. In 2008, Chera’s Crown Acquisitions joined with Kushner’s family business, The Kushner Companies, and the private equity firm The Carlyle Group to spend $525 million to buy the retail space at 666 Fifth Avenue, the skyscraper that marked Jared’s debut as a New York developer.

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“When you buy a building on Fifth Avenue, the first or second phone call you’re probably going to get is from Stanley,” Kushner said in a video tribute to Chera at a charity event in 2014.

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Fifth Avenue landlords described Chera as a dealmaker in real estate and politics — Senate Minority Leader Charles E. Schumer (D-N.Y.) and Israeli Prime Minister Benjamin Netanyahu were regular visitors to Chera’s office — and an adviser to his three sons and to other entrepreneurs.

Chera’s tenants included Versace, Cartier, Apple and, especially at his properties in New York’s outer boroughs, less well-known retailers such as pharmacies, gyms and other neighborhood services.

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Chera started out working at his father’s children’s clothing store, Suzette Kiddie Store, in downtown Brooklyn. Chera expanded the shop, later known as Young World, to several more branches. But he tired of paying rent.