While Trump Org. faces heat, Don Jr. roams

Scion is supposed to be in charge at the developer. His Instagram is all politics and play.

Donald Trump Jr. (Credit: Getty Images)
Donald Trump Jr. (Credit: Getty Images)

“Time for a little row on the lake. Great weekend outdoors… back to the grind tomorrow. #sunday #outdoors #weekend #rowing


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You may find him taking on a lake in the Catskills, or schmoozing with Republican National Committee officials in Miami (“these rock stars”). He can be seen mounting a bulldozer in Provo, Utah (“There’s nothing like playing with heavy equipment”), or hiking through the rugged hillside of Northeastern Spain.

One place you won’t see as much of Donald Trump Jr., however, is the office.

The eldest son of President Trump was made co-steward of the Trump Organization when his father moved to the White House in January of last year. It was quite an assignment: The development firm has been mired in scandal, with two unnamed executives under criminal investigation and the company itself facing a state tax investigation. Meanwhile, ambitious nationwide expansion plans for the firm’s hotel business, under the new brands “Scion” and “American Ideal,” have stalled.

In the midst of it all, Don Jr. has kept up a hectic travel schedule, lighting up both the campaign trail and the great outdoors with his antics and Instagram posts.

“It’s hard enough to run a successful business on a day to day basis,” said Jason Pereira, a partner at the Woodgate financial planning firm in Toronto, which counsels family businesses passing the reins from one generation to the next. “You have one bad thing happen, that’s ok. You have more than one bad thing happen simultaneously, then your attention is deviated.”

Don Jr. is far from the only New York real estate executive to indulge his wanderlust. Aby Rosen, the RFR Realty boss and a frequent Trump critic, is on an Italian yacht one week, whale-watching in the Galapagos the next. Fisher Brothers’ Winston Fisher recently ran seven marathons in seven days, from Miami to Marrakesh. But even among the jet set, Don Jr.’s attentions deviate extraordinarily from the company’s headquarters at Trump Tower, a review of his geo-tagged tweets and Instagram posts this year shows. And even if he announces that he’s “back to the grind tomorrow” after a Sunday on the lake, an escape to Paris, en route to a Monaco birthday bash, may only be some 48 hours away.

It’s politics that keep Don Jr. on the move just as much as freshwater fishing. Between December and July alone, he took more than a dozen politics-related trips, according to his social media posts. He campaigned for Rick Saccone in Pennsylvania, Ron DeSantis in Florida and Matt Rosendale in Montana. He attended the National Rifle Association’s annual meeting in Texas, an America First Action conference in Washington, D.C. and a Turning Point USA event in Palm Beach, Florida. He flew Air Force One with the president and spent time at the the White House.

The posts betray a longing for fatherly affection. “Cool pic leaving The White House with @realdonaldtrump earlier today,” he wrote on Instagram July 5. “Great to be with him for the day. Really miss seeing him on a regular basis.”


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Now that it’s midterm season, the Don Jr. show is officially on tour, traveling to Georgia, Texas, Kentucky, Colorado, Indiana, North Dakota, Ohio and Florida in roughly the last five weeks alone, all with the aim of whipping up the pro-Trump, Republican vote. Montana is both hunting ground and political stumping ground, a jaunt down to the nation’s capital can include an appearance at the Oval Office or an appearance at a movie premiere for the felon filmmaker Dinesh D’Souza, who was recently pardoned by the president.

It wasn’t supposed to be this way. In January 2017, then-President-elect Trump stood next to a giant pile of manila folders and vowed to build a wall between himself and the company that made him rich.

“My two sons, who are right here, Don and Eric, are going to be running the company,” Trump said. “They are going to be running it in a very professional manner. They’re not going to discuss it with me.”

Representatives for the Trump Organization did not respond to requests for comment for this story. Last year, some familiar with the Trump Organization’s workings told The Real Deal that Don Jr. had been mostly a nonentity within his father’s business, while others, like longtime company attorney Jay Neveloff, touted his abilities to “to make a deal.” When Don Jr.’s name popped up in Special Counsel Robert Mueller’s Russia investigation for meeting with a Kremlin-connected lawyer to get dirt on Hillary Clinton during the campaign, crisis-management experts, including Lanny Davis, now counsel to former top executive Michael Cohen, said Don Jr. had gotten in over his head.

“I thought I was out of politics after Election Day and could get back to my regular life and my family,” Don Jr. told the crowd at a GOP fundraiser in March 2017, according to NBC. “But I couldn’t.”

Even on apolitical trips, things get blurry. In late March, Don Jr. and Eric traveled to Dubai for the wedding of a daughter of Hussain Sajwani, the Trump Organization’s development partner at Trump World Golf Club Dubai. Also in attendance: the crown prince of Dubai, Hamdan bin Mohammed. The United Arab Emirates has spent over $27 million lobbying the U.S. government since Trump took office, and the Trump Organization continues to do business in the U.A.E. Last year, Sajwani’s company, Damac Properties, contracted a Chinese firm to start construction on the residential component of the Trump Dubai project.

Meanwhile, the Trump Organization is on the verge of more than one possible legal crisis. Apart from the Mueller investigation, Cohen pleaded guilty to charges that included hush-money payments to adult film actress Stormy Daniels, constituting illegal campaign contributions. The Trump Organization reported the payments as company expenses.

As a result, Manhattan District Attorney Cyrus Vance Jr. is investigating the firm’s role in the matter and that of two senior executives, who the DA could choose to indict. The top three executives at the firm are Don. Jr., Eric, and Allen Weisselberg, the company CFO who was subpoenaed by a grand jury in the Cohen probe. According to the terms of the president’s trust, it is these three men who together make decisions on how to manage Trump’s wealth.

Earlier this month, the New York State Department of Finance announced it would investigate unpaid gift taxes following a New York Times report about the accounting schemes alleged used by the Trump family over many decades. Crain’s reported that the unpaid tax bill could be as much as $400 million. And Letitia James, who will likely become state attorney general in January, has vowed to investigate herself. Facing such challenges, one might expect a company’s leader to get into the trenches. Don Jr., however, prefers a different vantage point.


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“This is what happens when someone bets me a good sum that there’s no way that the guy from New York City would swim in a gator infested swamp/bayou down in Louisiana. Easy money!!!”