Trump’s Most Controversial Business Moves That Paid Off Big and What We Can Learn From Them
Written by
Heather Altamirano
Edited by
Angela Corry
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Long before entering politics President Donald Trump was well known as a real estate mogul, a reality TV star and for his personal life playing out in the tabloids. His household name has been splashed on hotels, golf courses and high-rise apartment buildings and he’s always portrayed himself as a successful businessman, but not all of his dealings have been impressive.
Trump has filed bankruptcy six times and has several failed business ventures like Trump Steaks, Trump University, Trump Vodka, Trump Shuttle and more, according to AOL.
While many of Trump’s business decisions were unfruitful, he has had controversial moves that shockingly paid off. Here are three deals that were surprisingly successful and what others can learn from them according to experts.
The Grand Hyatt Renovation in NYC
In the 1970s Trump put himself on the map with New York real estate when he bought the Commodore Hotel next to Grand Central Terminal for an estimated $10 million, per the New York Times. He put another $70 million in for renovations and transformed the building into the Grand Hyatt Renovation, which was a major landmark of the city for decades.
“The city thought he was nuts,” money expert Andrew Lokenauth and founder of Be Fluent in Finance said.
It was a controversial move because Trump worked out a deal to receive a 40-year tax abatement from NYC for renovations during a time when the city was recovering from a crippling financial distress, per NPR.
“People were furious about giving tax breaks to a developer during a financial crisis,” Lokenauth said.
But that wasn’t the only thing people were upset about.
“Trump had zero experience with major hotel renovations, and many thought he’d fail spectacularly,” said Lokenauth. “Plus, he used incredibly aggressive negotiating tactics with the city — something I’ve seen sink many other developers — he even started construction before final approvals, which was a massive risk.”
However, his shrewd deal paid off, according to Lokenauth.
“The hotel became wildly profitable within two years and helped revitalize the entire area around Grand Central. I’ve run the numbers, and the return on investment was north of 400%.”
The lesson: It’s about timing and leverage.
“Trump saw value where others saw disaster,” Lokenauth said. “And he used the city’s desperation as leverage to get those tax breaks, adding the biggest wins often come from zigging when others zag.”
The Mar-a-Lago Purchase
These days Mar-a-Lago in Palm Beach, Florida is where Trump has glitzy parties, plays golf and resides when he’s not in the Oval Office. But it was once a rundown property that he bought in 1985 for roughly $10 million, according to the Associated Press.
“It was considered financial suicide at the time,” said Lokenauth.
Less than 10 years after buying the massive estate, Trump was in financial ruin after many of his deals failed and according to AP, he couldn’t afford the $3 million a year upkeep. To offset his costly expenses, he wanted to divide up the property lines and build mansions.
The Palm Beach elite were outraged.
“They fought him tooth and nail, claiming it would destroy property values and bring the wrong element to the area,” Lokenauth said.
The town rejected the proposal, but did approve Trump’s other idea of converting Mar-a-Lago into a private membership club where he charged pricey fees that covered his costs.
According to Lokenauth, it was a move that helped Trump in the end.
“He turned their opposition into free publicity,” he explained.
The lesson: Sometimes the strongest opposition indicates you’re onto something big. And controversy, if managed correctly, can be an incredible marketing tool.
“When everyone says you’re crazy, you might just be early,” Lokenauth said.
Renegotiating NAFTA and Pushing Through the United States-Mexico-Canada Agreement (USMCA)
In terms of politics, Trump has made many head-spinning controversial moves, but one business deal that turned out for the better according to Peter Diamond, a Federally Licensed Tax, Accounting, Real Estate, and Structure and Certified Bankability Expert® was renegotiating NAFTA.
Trump stated the North American Free Trade Agreement was “worst trade deal ever made” per CNN and campaigned back in 2016 to renegotiate, which he did. The new agreement went into effect July 1, 2020, and includes big adjustments on environmental standards, labor policies and many other areas between the U.S, Mexico and Canada.
According to Diamond it was a controversial move because Trump tackled a long-time trade agreement in an aggressive way that worked to his favor that other politicians wouldn’t touch.
“He used tariffs, tough negotiation, and raw pressure — especially against Canada and Mexico — to essentially force a rewrite of the rules,” he said. “That kind of hardline approach triggered backlash from economists, world leaders, and even members of his own party.”
Despite backlash, Trump successfully negotiated stronger protections for American manufacturing, digital trade, and intellectual property, Diamond said.
“It was one of the rare deals backed by both business groups and labor unions.”
According to AP, it wasn’t the economic booster Trump claimed, but it has a positive impact.
The lesson: “When you negotiate from a position of strength, you can drive results others said were impossible,” Diamond explained. “Most play defense while Trump played offense.”
While some might see Trump’s controversial moves that paid off as lucky breaks, Lokenauth sees something else.
“These moves show a pattern of seeing opportunity in controversy and using public opposition as a tool rather than an obstacle,” he said. “That’s something I emphasize in all my consulting work now.”
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