Great political dealmakers such as Abraham Lincoln, Franklin Roosevelt, Martin Luther King Jr, Lyndon Johnson and Ronald Reagan had similar traits (though all of them would have balked at the crudity of reducing the art of public leadership and democracy to simple dealmaking).
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Trump doesn’t plan. He doesn’t keep his insecurities in check. He puts his short-term emotional needs ahead of his long-term goals. And, he has traditionally seen what he would describe as “dealmaking” as performance art and a referendum on himself rather than the pursuit of an outcome that might benefit his company, community or country’s broader needs.
All of that is worth keeping in mind when trying to divine a strategy behind Trump’s fealty toward fellow authoritarians worldwide, his recent roller-coaster ride of tariff flip-flops, or his efforts to restructure government with a Muskovite sledgehammer instead of a scalpel.
There are certainly goals amid this dangerous yo-yoing. Trump is after personal and public hegemony for himself and the US, and he’s willing to tank the law, the Constitution and global alliances to get there. But it won’t follow a smooth path paved by some sort of nebulous proficiency at dealmaking. It will be haphazard. War, an economic recession and harmful policy dysfunction may accompany and outlast this cyclone.
Expect Trump and his acolytes to extol his dealmaking bravado anyhow because it’s a useful distraction. Trump has also been crafting those myths for quite some time, and he won’t let go of them. He published The Art of the Deal, a nonfiction work of fiction, in 1987. “Deals are my art form,” he allowed in the book. “Other people paint beautifully on canvas or write wonderful poetry. I like making deals, preferably big deals.”
Trump is after personal and public hegemony for himself and the US, and he’s willing to tank the law, the Constitution and global alliances to get there.
That was written when few in the business world who were authentically serious dealmakers regarded Trump as a capable deal guy, especially in a city as brawny and competitive as New York.
In fact, he bungled a series of deals back then that might have granted him standing as a pivotal “dealmeister” in New York – including major belly flops involving Manhattan’s West Side Yards and the Plaza Hotel. Ed Koch, a New York mayor who knew a thing or two about political deals, outmanoeuvred Trump around the Yards. Robert Bass, a Texas billionaire who knew a thing or two about business deals, took Trump to the cleaners on the Plaza sale.
A vicious cycle of six corporate bankruptcies followed that period and unspooled Trump’s biggest real estate and casino holdings, despite magazine covers that once proclaimed him as a deal god. His father’s riches helped him avoid personal bankruptcy. But then The Apprentice came along, and TV reinvented Trump as the dealmaking guru to the masses. He kept working that line as he zeroed in on politics.
“We need a dealmaker in the White House who knows how to think innovatively and make smart deals,” he tweeted in 2011. “If I’m president, there won’t be stupid deals any more,” he noted in 2016.
After capturing the White House in 2016, he led as he does now: willy-nilly. The signature accomplishments of his first term – seating three conservative justices on the Supreme Court, engineering a tax overhaul and passing criminal justice reform – were initiated and guided by other, more capable Republican dealmakers. When challenged by crises such as the COVID-19 pandemic that didn’t lend themselves to his brand of wheeling and dealing, he initially meandered. Lives were lost.
Still, Trump stayed on message.
“We never make good deals, at anything,” he said during his presidential campaign last year.
So, the dealmaker is back for a second Oval Office residency. Tariffs, inflation, jobs, markets, civil rights, the rule of law, global stability and the future are in play. And Trump has advice to share.
“You should’ve never started it; you could’ve made a deal,” he counselled Zelensky recently, accusing the Ukrainian leader of starting a war he didn’t start and recommending a deal he couldn’t have forged.
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However shambolic and inscrutable Trump’s see-sawing may appear, White House press secretary Karoline Leavitt recently told the New York Times that Americans like it that way. They “recognise the beauty of the art of the deal”, she said.
Anyway, it’s not deals, per se, that are motivating Trump. What he truly relishes is putting the public, policymakers, investors and allies off balance in the same way kids like playing hide-and-seek. It leaves people guessing and keeps him in the spotlight and in control of the narrative.
And he intends to make a big deal out of it.
Timothy L. O’Brien is the senior executive editor of Bloomberg Opinion. A former editor and reporter for the New York Times, he is the author of TrumpNation: The Art of Being the Donald.
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