This article is taken from the May 2025 issue of The Critic. To get the full magazine why not subscribe? Right now we’re offering five issues for just £10.
Some people are motivated by money. Others are driven by fame, a need to be liked or an urge to be remembered as a great individual in the annals of history. Donald Trump seems to want all of the above, plus the self-assurance that he can, in fact, solve those unending, sticky international problems no man or woman before him could adequately tackle.
Trump is also obsessed with making deals — or at least being perceived as someone who can. “Deals are my art form,” he tweeted on 29 December 2014, long before he was considered a serious political force in America. “Other people paint beautifully or write poetry. I like making deals, preferably big deals. That’s how I get my kicks.” Fast-forward to this February, and he was pretty much singing the same tune: “That’s what I do, I do deals, my whole life is deals, that’s all I know is deals.”
Trump’s second term is not even four months old yet, but the president has dived head-first into the choppy waters of international diplomacy, where failure is frequently the rule rather than the exception. Whether it’s the war in Gaza, the war in Ukraine, tariffs or immigration enforcement, Trump doesn’t like to waste time. He’s notoriously impatient and wants things to happen almost instantaneously — and it shows.
It’s part Madman Theory — do what I want immediately or you will suffer the kinds of consequences that no rational person would dare contemplate — and part laissez-faire. Nothing is off limits.
★
Trump’s history of deal-making in the international arena, however, has been less than stellar. Trump is doing everything, everywhere, all the time, but the results are about as inconsistent as his ideology. This isn’t to suggest Trump hasn’t had any success. Whilst the 2020 Abraham Accords weren’t the groundbreaking peace initiative Trump or his advisers claimed, the agreement was historic in that it established formal diplomatic relations between Israel and the United Arab Emirates for the first time.
The first Trump administration got the US out of an unwinnable morass in Afghanistan when it signed the Doha Agreement with the Taliban. That required a significant amount of courage on Trump’s part, given the red-faced objections from the US national security establishment that inevitably ensued.
A lot of potential deals, however, were also left on the table. The Israeli–Palestinian peace process was dead when Trump came into office the first time in 2017 and remained dead when he left. The trade deal with China, which required Beijing to purchase an additional $200 billion in US products, was hit by the global Covid-19 pandemic, which meant the Chinese never kept to its terms. His summitry with North Korean leader Kim Jong Un was daring and worth a shot since previous American strategies with Pyongyang had all failed. However, nothing came of the showy statesmanship outside of a temporary halt to North Korean long-range missile tests.
★
Trump vowed to strike a bigger, better, stronger nuclear agreement with Iran, Washington’s favourite adversary, but in the end made things exponentially worse by ripping up a fairly decent Obama-era accord that kept Tehran’s enrichment program in a box.
The alternative Trump offered was full capitulation by Tehran in return for US sanctions relief, an outcome that was about as likely as Iran’s 85 year-old Supreme Leader, Ayatollah Ali Khamenei getting pissed in a South London pub. Instead, Iran, a nation with an economy roughly the size of Missouri, did precisely the opposite: churning out more, higher grade uranium; installing faster centrifuges in its enrichment plants and sabotaging oil tankers in the Persian Gulf to ensure Washington understood that if Tehran can’t export its oil, then nobody can.
The first months of Trump’s second term has continued the pattern. True to form, he is throwing sticks at pretty much anybody he can reach, forever confident in the belief that the United States is so wealthy and powerful that the side getting hit in the face will have no choice but to eventually cater to his demands. This strategy has earned him a few notable policy wins thus far, particularly in the Western Hemisphere, America’s exclusive sphere of influence ever since the Monroe Doctrine was coined in 1823.
Whether or not Trump’s threats of retaking the Panama Canal are serious — and let’s be honest, the answer might depend on the day — the Panamanian government is seeking to mollify Washington’s ire by offering concessions, from withdrawing from China’s Belt and Road scheme to pressuring a Hong Kong shipping conglomerate to sell two ports on either edge of the waterway.
Colombia’s Gustavo Petro, who tried to stand up to Trump on migration, was instead batted on the head like a schoolboy and threatened with severe economic penalties if he didn’t change course (he did). Guatemala, El Salvador and Costa Rica, all of which depend on the US market for their exports, have essentially agreed to be the enforcers of Trump’s immigration and deportation policies.
Trump is also having a bit of success with Mexico, whose new administration headed by Claudia Sheinbaum is not only accelerating operations against the cartels but doing things that previous Mexican governments were loath to do, such as handing 29 high-profile narcotraffickers over to the US for prosecution.
These successes aside, the all-sticks, no-carrots approach is not without its faults. Nor is it destined to work on all countries. Those pleasant Canadians up north, for instance, are quite mean nowadays, responding to Trump’s tariffs and incessant humiliations about becoming America’s 51st state with retaliatory boycotts and tariffs of their own.
The EU doesn’t appear like it’s going to roll over either. Russia, meanwhile, is slow-walking Trump’s Ukrainian peace gamble by issuing clarifications, asking for mundane details and linking short-term ceasefires to conditions — like re-linking certain Russian banks to the Western financial system — that Europeans to this date refuse to grant.
★
So the question must be asked: how artful are the Donald’s deals, really? His many haters insist he’s more of a showman than a statesman, a loud carnival-barker with the attention span of a gnat. His committed supporters describe him as the most gifted negotiator on the planet with a supranatural ability to strike an agreement on his terms. The truth is likely somewhere in the middle: he can obviously make agreements, assuming he can also temper his conflicting impulses.
Iran is a perfect case-study. On the one hand, it’s crystal clear that Trump wants to strike a deal with Tehran and would much prefer to leave the military option on the shelf. Even during his first stint in office, when he brought Iran’s crude oil exports down by more than 80 per cent and froze tens of billions of dollars in Iranian financial reserves, he was pontificating about renting out a conference room somewhere and sitting down with the Iranians to work it out diplomatically.
In September 2019, when US–Iranian relations were in a tailspin, Trump agreed to participate in a phone call with then-President Rouhani; the call never happened because Rouhani suspected Trump was trying to use him as a prop to burnish his political credentials back in the States.
Yet on the other, Trump periodically bombed Tehran’s armed proxies in Iraq and Syria, killed Iran’s most celebrated warlord by authorising a strike against his convoy on the outskirts of Baghdad — risking a war in the process — and hired advisers (like John Bolton, Elliot Abrams and Mike Pompeo) who were more interested in overthrowing Iran’s leadership than they were in getting the deal their boss purportedly craved.
★
The ambivalence remains. Earlier this year, Trump sent a letter to Khamenei asking for another round of diplomacy on the nuclear file, only to order B-2 strategic bombers to deploy to the base in Diego Garcia in a not-so-subtle attempt to send Tehran a message. When Trump signed a 4 February executive order reimposing his maximum pressure strategy on Iran — one of the goals of which is to “drive Iran’s export of oil to zero” — he was noticeably sombre during the ceremony.
Stressing he was “torn” about the document, Trump exclaimed that he hoped it wouldn’t need to be used. “The Iran situation, hopefully, I’m going to sign it, but hopefully, we’re not going to have to use it very much,” he told the assembled press. “We will see whether or not we can arrange or work out a deal with Iran. And everybody can live together. And maybe that’s possible and maybe it’s not possible. So I’m signing this, and I’m unhappy to do it. But I really have not so much choice because we have to be strong and firm.”
Trump’s team is as split on the Iran issue as he is. Steve Witkoff, the administration’s envoy to the Middle East, is talking about a new Iranian nuclear agreement that will provide assurances that Tehran is not militarising its enrichment programme — in other words, a deal that sounds quite similar to the one Trump flushed away seven years ago.
National Security Adviser and serial Signal misadministrator Michael Waltz is, however, jumping on television and essentially reading the Iranian regime the riot act: dismantle your entire program, root and branch, in full view of international inspectors or face the scary consequences. The first is the pragmatic path; the second is the war path.
Which one will Donald Trump choose? At the time of writing, Trump is giving diplomacy a go and dispatching Witkoff to see if an agreement is possible. Whether he persists or loses his patience as he so often does will determine how much of a dealmaker he truly is.
