“Deals are my art form,” Donald Trump boasted in his signature book, 1987’s The Art of the Deal. “Other people paint beautifully on canvas or write wonderful poetry. I like making deals, preferably big deals. That’s how I get my kicks.”
In the second term of his presidency, Trump is still getting his kicks quite often. His approach to deal-making, however, no longer resembles an artform–if it ever did–so much as it does a game of Russian roulette: erratic, overconfident, and mutually destructive. Through his whiplash-inducing tariff flip-flops and shabby treatment of Ukraine, Trump is demonstrating how his idea of a “good deal” differs from the rest of the world’s. He’s also assuring other leaders they’d do well to avoid sidling up to his negotiation table unless they absolutely have to.
While many leaders surely have their own little idiosyncrasies around what constitutes a good deal, there seems to be some general consensus in the business world. The business book canon is brimming with tomes like William Ury’s Getting to Yes, which emphasize the importance of mutual respect and collaboration in forging win-win outcomes, while Harvard Law School’s Program on Negotiation prizes clarity and fairness. And beyond the realm of pure business, the last century of diplomacy was built on deals that were fair and equitable, and where all parties stood to gain something.
Think of the Marshall Plan in 1948, when the U.S. provided over $13 billion to help post-WWII Europe rebuild itself–with the U.S. gaining strong trade partners, political allies, and immeasurable goodwill in return. Or the Camp David Accords in 1978, where Israel got security provisions, Egypt reclaimed some of its lost territory, and the U.S. burnished its ties with both countries in brokering the deal. These mutually beneficial moments from the highlight reel of international history are about as close to universally recognized good deals as they come.
It’s unclear, however, if Trump would see them that way.
“You hear lots of people say that a great deal is when both sides win,” the president wrote in his 2007 book, Think Big and Kick Ass. “That is a bunch of crap. In a great deal, you win—not the other side. You crush the opponent and come away with something better for yourself.”
In Trump’s philosophy, deals are evidently a zero-sum game with clear winners and losers and no set rules. Forged in the fires of New York City real estate in the 1980s, this outlook ultimately shaped Trump’s first term as president, where he deployed extortion-like tactics to beef up his bargaining position. Sometimes he prevailed; other times, he didn’t. But he almost always operated by creating a potential crisis and dangling a solution advantageous only to himself.
In 2018, he was able to forge the United States Mexico Canada Agreement (USMCA), a revised version of the North American Free Trade Agreement (NAFTA), only by threatening to withdraw the U.S. from NAFTA, or purge Canada from it. Later that year, after the Senate unanimously passed a stopgap bill to continue funding the government, Trump refused to get behind it unless the bill included $5.7 billion for his border wall. In this case, the threatened crisis came to pass, resulting in the longest government shutdown in U.S. history… with no additional border funding. And perhaps the most notorious “deal” from Trump’s first term came during fall of 2019, when he paused a promised $400 million in military aid to Ukraine, allegedly to pressure the country into investigating Joe Biden’s son, Hunter. The deal was technically a success, in that Ukraine did indeed pursue such an investigation, but the victory was short-lived, in that it eventually earned Trump his first of two impeachments.
Trump’s coercive approach to deal-making was a decidedly mixed bag in his first term. Any hopes that he might rein in his impulses and apply a more mutually beneficial touch the second time around, however, vanished immediately after January’s inauguration. How the rest of the world would respond to Trump’s extractive tactics, now that the surprise factor is long gone and unpredictability is just baked into the equation, remains an open question.
Ukraine has very little leverage, for instance, in ongoing negotiations with the Trump White House to end three years of Russian-led war. During an ill-fated Oval Office meeting on February 28, which had been expected to firm up plans for peace talks between Ukraine and Russia, President Volodymyr Zelenskyy seemed caught off guard by Trump and JD Vance’s demands for a display of gratitude. (It’s unclear now whether the meeting was indeed meant to advance negotiations, or if it was intended as more of a planned humiliation ritual.) In the aftermath, Trump paused aid to Ukraine, along with intelligence-sharing. He will reportedly resume both, and broker peace talks with an apparently blameless Russia, once Zelenskyy not only agrees to share minerals with the U.S., but undergoes an attitude adjustment. (Zelenskyy seems to be relenting.)
Iran, on the other hand, is calling Trump’s bluff. The president reportedly sent a letter to Iran’s Supreme Leader Ayatollah Ali Khamenei last week, threatening military action if the republic refuses to negotiate over Iran’s nuclear program. “There are two ways Iran can be handled,” Trump told Fox Business on Friday, “militarily or you make a deal.”
So far, Khameni refuses to make a deal.
“The insistence of some bullying governments to negotiate is not to solve problems, but to impose their own expectations,” the leader said, according to Iran’s state media. “The Islamic Republic of Iran will definitely not accept their expectations.”
The ball is now back in Trump’s court to either follow through with a military attack on Iran–not likely a popular option in Congress at this particular moment–or let his empty threat hang in the air. For now, he seems content to do the latter.
One form of deal-making where Trump has produced unquestionable results in his second term, though, is through his liberal use of tariffs. Not that those results have all been positive, exactly.
Trump scored an early win through using tariffs as a cudgel, just days after his inauguration. On January 26, Colombia objected to accepting deported migrants from the U.S. that were flown in on military planes, shackled in handcuffs. In response, Trump threatened the country with 25% tariffs. Colombia quickly backed down. Although the country’s objection resulted in better treatment for its deported migrants, the standoff was viewed by many as an unequivocal success for Trump’s tariffs. It would prove to be the last one to date.
Trump initially promised that 25% tariffs on Canada and Mexico would begin on February 4. After the stock market appeared spooked in response, though, and both countries tentatively agreed to beef up border security, he delayed the tariffs for a month. After briefly musing that he might further delay the duties, until April 2, Trump went ahead with applying 25% tariffs against Mexico, Canada, and China on March 4. Since then, amid pandemonium at the stock market, he has delayed some of these tariffs until April 2, but confusingly left others in place. (Even more confusing, he has placed tariffs on steel and aluminum imports, which automakers depend on, and increased them again on Tuesday, while also attempting to minimize disruption to the auto industry with an executive order.) Meanwhile, Canada has not paused its retaliatory tariffs, and neither has China, who seems completely unfazed by Trump’s trade war.
These “deals” seem less like the five-dimensional chess moves of a savvy tactician than the arbitrary flailing of a leader drunk on power and an expectation of always getting his way. He has reserved a special animosity toward Canada, framing the trade war as an effort to force the country into becoming the U.S.’s 51st state, despite very little stateside enthusiasm for the idea. Whatever meager concessions the U.S. has gained in border security from this multi-front trade war are vastly dwarfed by the economic turmoil of a spooked stock market, fears of an approaching recession, and global animosity toward the U.S.
Trump may see deal-making as a show of power, but his deals in 2025 seem to only show the power of indiscriminate destruction. Forget “mutually beneficial”; Trump now seems all too willing to make moves that benefit no one. And if he keeps it up much longer, even some of his most ardent voters may soon conclude they got a raw deal.
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