This was supposed to be Don Jr.’s time as a real estate macher. Then came the emails

"There’s a clear hierarchy in the firm, and the father sits on top of it."

Donald Trump Jr. (Background image credit: Getty Images)
Donald Trump Jr. (Background image credit: Getty Images)

“If it’s what you say I love it”

That’s what Donald Trump, Jr. told a quirky British publicist who promised him Russian-stamped dirt on Hillary Clinton during the 2016 presidential campaign.

A series of reports by the New York Times this week, amplified by Don Jr.’s shifting responses to them, thrust the president’s oldest son and Trump Organization executive vice-president into the national spotlight. But in New York’s real estate industry, where Don Jr. spent years trying to emerge from under his father’s immense shadow, he is still not a well-known figure.

President Trump’s election victory and his decision to pass the family company’s management onto his sons finally seemed to offer Don Jr. a chance to become more than his father’s son. He announced plans for the company’s national expansion, and even entertained the idea of running for governor. Then, the email scandal broke. Now some observers fret he is in over his head.

“I do think he was bitten by the political bug, and I think this whole presidential election went to his head and I think it changed him,” said Louise Sunshine, the former Trump Organization executive and new development marketer who has known Don Jr. since he was a child. “It changes a lot of people.” As for how Don Jr. should be working to limit the fallout from the emails,  Sunshine said he’s in desperate need of people from outside the family to guide him.

“You have to have very good advisors,” she said. “And who are his advisors? No one.”

A spokesperson for the Trump Organization did not return a request for comment. Trump, as part of a brief statement addressing the emails, said: “Don is — as many of you know Don — he’s a good boy.”

“None of us know his children.”

Many close to the Trump Organization, like its longtime real estate attorney Jay Neveloff, speak positively of Don Jr., calling him a smart and effective dealmaker, who, although more low-key than his gregarious father, is still sincere and engaging.

“He’s such a good guy and he knows how to make a deal,” Neveloff said. “My heart’s breaking for him in this situation and I think I could take the same facts and spin them differently and it would be a non-story… I’ve had more meetings with Russians claiming something than I should have had,” he quipped, citing numerous sit-downs with Russian attorneys and investors promoting deals that ultimately went nowhere.

Gil Dezer, himself the son of a real estate magnate and a partner of the Trumps on six developments in South Florida, called Don Jr. “a guy’s guy” who is “extremely intelligent and very quick, very quick.” 

“The entire Trump family works 28 hours a day, they manage everything, it’s amazing how they do it,” Dezer said. “You go out with these people and you almost feel like you don’t work [compared to them].”

But exit Trumpland, and New York and Florida real estate executives have little to say about the man.

“I honestly never heard anything about his business dealings,” said Stephen Kliegerman, the president of Halstead Property Development Marketing.

In New York City, being the oldest son in a well-known real estate dynasty usually confers upon you princeling status. Jared Kushner, the 36-year-old son of developer Charlie Kushner, took over the family business when his father went to prison in 2005 and quickly gained considerable clout. Jerry Speyer’s son Rob now runs Tishman Speyer and became chair of the powerful Real Estate Board of New York in 2013. It was a borderline scandal when the late developer Seymour Durst skipped over his eldest son Robert to name Douglas the heir to the throne.

Some observers argue that the main reason Don Jr. doesn’t have Jared-esque standing is that his father won’t let him.

“When you have such an overbearing father, what do you expect?” said Michael Stoler, a Madison Realty Capital executive who hosts the long-running, industry-focused TV show The Stoler Report.

“There’s a clear hierarchy in the firm, and the father sits on top of it,” said Roy Stillman, a developer who partnered with Trump on a Fort Lauderdale hotel project in the mid-2000s that ended in a legal battle between the two sides.

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But Trump’s long shadow can’t explain why Don Jr.’s siblings, Eric and Ivanka Trump, appear to have left a greater impression.

“Everybody knows Eric, not that many people know Donald Jr.,” said George Arzt, a Democratic consultant who has represented the likes of Gary Barnett and the Milstein family. “I always found Ivanka and Eric more approachable than their brother,” added Kliegerman.

Joseph Cayre, the founder of Midtown Equities who spent election night celebrating with Trump and other close associates at New York’s Hilton hotel, said he had never met Don Jr.  When asked if any of his friends and colleagues in the business knew Don Jr., he replied: “None of us know his [Trump’s] children. We know him and his son-in-law.”

“I don’t know Donald Trump, Jr.,” said Jeff Greene, the real estate investor, former Palm Beach neighbor of Trump and frequent visitor to the president’s Mar-A-Lago resort. Greene, echoing the sentiments of several others who spoke to The Real Deal, said that Ivanka was always the more sociable of the clan. “I don’t see them” Greene said of the sons. “They’re kind of invisible. I never read about [Don Jr.] and I never hear about him doing anything…Donald Trump [Sr.], he makes an effort with the high profile people at Mar-a-Lago, like with me, maybe because I’m his former neighbor and a billionaire… The sons, if I were one of the sons, I would have been doing a lot of that.”

“In 30 years working in this business, I’ve never seen him at any major real estate events” said Roxanne Donovan, a real estate publicist who counts Savanna and HFZ Capital Group among her clients. RXR Realty’s Scott Rechler said likewise: “I never ran into him and don’t think he has been active in the New York real estate industry scene,” he said.

Others said they had only ever encountered Don Jr. at the annual holiday parties of a popular freelance real estate reporter who was close to many industry bigwigs. Attendees of those parties said Don Jr. developed a close friendship with the reporter, Lauren Price, who died of cancer. He is said to have never missed a get-together at Price’s one-bedroom apartment on the Upper West Side.

For years now, the Trump Organization hasn’t been a traditional Manhattan real estate developer. It mostly relies on licensing deals instead of equity ownership, with a focus outside of New York City. The company is, however, aggressively positioning for a national expansion, and has already almost fully transitioned to a hotel-focused model around the U.S. and abroad. In September, it announced the launch of a new boutique hotel brand, Scion, although licensing deals have been slow to get off the ground. Its first reported licensing partner, a developer in Dallas, decided to drop project plans in April.

New York is still on the company agenda, though, at least according to Eric Trump. In an interview with TRD last year, Eric said “there’s no question we’ll do something in Manhattan again.”

Crisis management 101

On June 5, Don Jr. announced the Trump Organization’s latest hospitality brand, dubbed American Idea. “Eric and I got a great crash course in America over the last two years,” he said. “We saw so many places and so many towns and heard so many stories that were so touching. People that were so excited about the prospect of this country and Americana in general.”

But now, steeped in scandal for what critics are calling collusion with a hostile government, could Don Jr. remain the flag-bearer for American Idea? It’s a legitimate question for observers of the firm, who wonder whether the scandal could make it harder for him to do his job.

“This would be a very poor time for Don Jr. to be speaking out about something else” other than the email scandal, Stillman said, “because there is nothing else. They’ve been trying to change the narrative but it’s like gum under their shoe.”

Lanny Davis, an attorney and crisis-management specialist who represented President Bill Clinton during his late-1990s impeachment trial, said Don Jr. had so far broken every rule in the book in his attempts to mitigate the potentially damaging revelations of the Russia story.

“He hasn’t missed one opportunity to make a mistake,” Davis said. “He even screwed up when he did the right thing, by putting out the email chain, but he wasn’t honest about why he was doing it. And he allowed his father to be dishonest by saying he was being transparent.”

“I don’t think he is managing the crisis, he never has been,” said Eric Dezenhall, who worked in President Ronald Reagan’s White House and has captained crisis situations for companies like ExxonMobil. Still, he’s not sure if Don Jr.’s gaffe will hurt the business.

“If the Trump business were in software or if they were a big accounting firm this would be a whole other conversation, but they’re land peddlers, so I’m not sure if an investor in Malaysia really gives a damn about any of this stuff,” he added.

Others said balancing the unwanted public attention with work responsibilities was doable, but would require a great deal of outside help and focus.

“Being in the middle of an investigation has clearly got to be a distraction,” Neveloff said. “But you can still run a business.”