Lexington
Donald Trump and the art of bad diplomacy
April 10, 2026
When it comes to dealing with Iran, the Donald Trump of 1987 offers helpful advice to the Donald Trump of today. In “The Art of the Deal”, a ghost-written book, he warned that: “The worst thing you can possibly do in a deal is seem desperate to make it. That makes the other guy smell blood, and then you’re dead.” If only President Trump had listened to his younger self. Since Iran blocked the Strait of Hormuz, sending the global economy into conniptions and American petrol prices to $4 a gallon, he has shown several signs of desperation to make a deal.
Anxious to calm markets, Mr Trump declared on March 30th that he had made “great progress” towards a deal with “a new, and more reasonable, regime”; and that if such a deal was not reached, he would completely obliterate Iran’s power stations and perhaps its desalination plants. The next day, he said America would end the war in two or three weeks, and that opening the Strait was something other countries would have to deal with. In the past he has issued incendiary threats on a Saturday, when markets are closed, only to walk them back just before markets opened again. The White House promised an “important update” on April 1st, after this column’s publication.
Iran smells blood. Realising that Mr Trump is scared of economic disruption, and that cheap drone attacks and even cheaper threats can cause a lot of it, the Islamic regime has kept up its attacks and threats. It has allowed only a few tankers through the Strait of Hormuz, sometimes charging a reported $2m per ship. On March 27th Marco Rubio, America’s secretary of state, lamented that Iran’s leaders “may decide that they want to set up a tolling system in the Strait”. Naysan Rafati of the International Crisis Group, a think-tank, calls this the “Ayatollbooth” strategy. It violates global norms of free navigation—and could be copied by other belligerent states. The Houthis in Yemen have form.
Another nugget from Mr Trump’s book is that “You can dream great dreams”, but “they’ll never amount to much” unless you “contain the costs”. Commander-in-chief Trump has ignored this wise advice. The Pentagon is asking for another $200bn, and the indirect costs of the war may be much larger. If prolonged, it could knock 0.5% off global gdp next year and add 0.9 percentage points to inflation, estimates the oecd. It could also aggravate global hunger by throttling the supply of fertiliser. All this is alienating America’s allies and weighing on Mr Trump’s poll numbers. The Economist‘s tracker calculates his net approval is -20%.
How did Mr Trump get in this mess? With a mixture of vengeful aggression and blinkered optimism, suggests “The Art of the Deal”. If someone does you wrong, “Fight back very hard,” it says. “The risk is that you’ll make a bad situation worse, [but] things usually work out for the best in the end.”
President Trump has consistently followed this advice. Sometimes, it has worked out well for him. Not a single American soldier was killed when he sent special forces to snatch Nicolás Maduro, the rogue leader of Venezuela, and installed a friendlier successor. In Iran, by contrast, his war has so far yielded few benefits besides the destruction of much of Iran’s conventional arsenal. The regime retains its stash of highly enriched uranium, and now has an even stronger reason to build a bomb. Iran’s leaders have probably concluded they would “be better off with a nuclear weapon”, says Jeanne Shaheen, a Democratic senator from New Hampshire, “because then maybe [America] would be treating them the way we’re treating Vladimir Putin.”
On March 27th an expeditionary force of marines arrived in the Gulf, suggesting that once again Mr Trump plans to “fight back very hard”. “If he stays, he escalates,” predicts Thomas Wright, a former member of President Joe Biden’s National Security Council. That could mean seizing Iran’s oil terminals on Kharg Island, or trying to clear coastal areas of Iranian forces that threaten ships, or even a raid deep inside Iran to grab its uranium stockpile.
American voters think this would make a bad situation worse. Fully 62% oppose a ground war; only 14% are in favour. Mr Trump no doubt wishes to avoid a quagmire. Alas, the current negotiations between Iran and America, conducted via intermediaries, are “destined to fail”, says Mr Wright. One obstacle is a complete absence of trust. In his book, Mr Trump admitted that his dealmaking depends on lying, or “truthful hyperbole”. Iran’s leaders seldom trust American presidents, but they have particular reasons to doubt Mr Trump. He tore up an agreement America had signed with Iran under President Barack Obama, and has greenlit bombing raids ahead of scheduled talks.
Now, Mr Trump’s 15-point list of demands assumes that Iran will make tangible concessions, such as handing over its highly enriched uranium and surrendering its long-range missiles, in exchange for a promise—that Mr Trump will not break a ceasefire deal. If they deem his word worthless, that could be a tough sell. On March 29th the speaker of Iran’s parliament said: “The enemy publicly sends messages of negotiation and dialogue while secretly planning a ground attack.”
A lack of trust also weakens Mr Trump’s position at home. maga Republicans tend to believe that if Mr Trump says the war is necessary, it probably is. Other Americans are more sceptical. Only 22% think the war will make them safer, according to Pew, a pollster. Senator Shaheen says there has been “no transparency with the American public” about the war, and that Mr Trump does not always act in America’s best interests. Asked if, in the classified briefings she receives as a member of the Senate Armed Services Committee, she has heard evidence that the situation is better than it appears, she replies, simply: “No.” ■
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