Why Trump’s ‘dealmaker’ image faces scrutiny as Iran, Ukraine wars test his negotiating skills

US President Donald Trump built his political identity around a simple promise: he could strike “deals” that traditional politicians could not.

From repeatedly claiming he could end wars to attempting to reshape global trade through tariff threats, Trump has presented himself as a negotiator capable of turning pressure into results.

But his record in the White House is raising questions about the limits of that approach.

Trump’s reputation as a dealmaker predates his political career. In 1982, shortly after Trump Tower opened in New York, the then 38-year-old developer suggested he could negotiate arms-control agreements with the Soviet Union better than President Ronald Reagan. His 1987 book, The Art of the Deal, later cemented that image.

Four decades on, the same persona remains central to his presidency. Yet the conflicts involving Iran and Russia, alongside trade disputes triggered by his tariff policies, have highlighted the challenges of translating ambitious promises into lasting outcomes.

“He’s not as good at this as he thinks he is,” Christopher Preble, a senior fellow at the Stimson Center, an international security think tank, told the Associated Press.

From ending wars to tariff diplomacy

Trump promised to end Russia’s war in Ukraine within a day, but the conflict continues. His handling of Iran has also drawn scrutiny. After projecting confidence in a swift outcome, he announced what he called a “great” ceasefire, which quickly faltered.

His repeated assertions that Tehran was eager to negotiate have not consistently produced the outcomes he had described.

Trade policy has presented another test. Trump argued that tariffs would give Washington leverage to secure favourable agreements.

However, unilateral duties have fuelled trade tensions, including with Canada, while raising costs for American businesses and consumers.

A zero-sum approach to negotiations

Trump’s negotiating style took shape during decades in real estate, where aggressive bargaining and high-risk ventures helped build his public profile. His business career, however, also featured financial setbacks, bankruptcies and legal disputes involving contractors, business partners and creditors.

Marty Latz, a negotiation expert and author of The Real Trump Deal, told AP that Trump had secured some successful agreements but had also experienced major failures.

Barbara Res, a former Trump Organization executive responsible for construction, argued that Trump’s personal pride could complicate negotiations.

“He could be a better negotiator if his ego didn’t get in the way,” Res said, according to AP.

Trump’s preference for presenting negotiations as contests with winners and losers can project resolve. But diplomacy often requires compromise, sustained engagement and confidence that commitments will be honoured — conditions that can be difficult to establish through threats alone.

How television reinforced Trump’s dealmaker image

The 2004 debut of The Apprentice gave Trump’s business persona a fresh platform.

The reality television show portrayed him as a decisive executive who evaluated contestants and controlled the boardroom, reinforcing an image that later became central to his presidential campaigns.

Tim O’Brien, author of TrumpNation: The Art of Being The Donald, told AP that unpredictability was central to Trump’s negotiating style.

“If he’s the one causing the chaos, he’s often the only one who can end it,” O’Brien said.

Trump outlined his approach in The Art of the Deal: “I aim very high, and then I just keep pushing and pushing and pushing to get what I’m after.”

Such tactics can create leverage, but they can also harden opposition when counterparts refuse to yield.

The White House has defended Trump’s record, citing trade agreements and investment commitments as evidence of his negotiating abilities.

Trump’s supporters also point to the Abraham Accords, negotiated during his first term, as a significant diplomatic achievement.

His business career, meanwhile, involved extensive litigation. Latz has argued that legal disputes could serve as bargaining tools to pressure counterparties or reduce financial liabilities, according to AP.