Trump’s dealmaking is all about him

By Timothy L. O'Brien

Marco Rubio advised ABC News last week that negotiating prowess was a key to understanding why President Donald Trump had been cozying up to Vladimir Putin despite Russia’s brutal and unrelenting invasion of Ukraine.

“We have to bring them to the table. You’re not going to bring them to the table if you’re calling them names, if you’re being antagonistic,” the secretary of state noted. “That’s just the president’s instincts from years and years and years of putting together deals as someone who’s in business.”

Rubio was grasping at straws, of course. He had sat idly by two days earlier at the White House while Trump and Vice President J D Vance gave Ukraine’s leader, Volodymyr Zelenskyy, a searing, reckless tongue-lashing in front of reporters and the rest of the world. The perils of name-calling and antagonism hadn’t restrained Trump in that instance — hardly a surprise given his long-standing preference for flame-throwing whenever he has encountered lackluster obeisance.

Rubio was also defaulting to a version of Trump that loyalists or those unfamiliar with his journey invoke when they have to explain away his unpredictability, unreliability and irrationality: Trump the epic dealmaker and 3D chess player. This is a useful meme to trot out when chaos is afoot. Just calm down, the architect is burning down the house because he’s a master-builder.

Truth be told, Trump has never been a particularly good dealmaker. Self-promotion and reading his audience’s needs are his strong suits. Great dealmakers in the business world aren’t emotional and erratic. They’re self-possessed. No examples are perfect, but an old school version of this is Warren Buffett. He has quietly gone about his business for decades, taking meaty, strategic stakes in big companies without ruffling feathers and often extracting outlandishly favorable terms along the way. A new school version is Mark Zuckerberg, who sewed Instagram and WhatsApp into Facebook’s fabric surgically and unemotionally (no matter what trustbusters think about the outcomes).

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).

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.”

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 deal-meister 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, outmaneuvered 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 anymore,” 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 counseled Zelenskyy recently, accusing the Ukrainian leader of starting a war he didn’t start and recommending a deal he couldn’t have forged.

However shambolic and inscrutable Trump’s see-sawing may appear, Karoline Leavitt, a White House spokeswoman, recently told the New York Times that Americans like it that way. They “recognize 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.