Trump’s ‘Art of the Deal’ is nowhere to be found in talks with Ukraine

President Trump’s Oval Office clash with Ukrainian head of state Volodymyr Zelensky was exactly the boon Moscow desired: the diplomatic fracture it created will only serve to further Russia’s aims. In pursuing negotiations with Russian strongman Vladimir Putin, self-declared master deal-maker Trump seems to have abandoned key tenets of his own 1987 book, "The Art of the Deal."

“The worst thing you can possibly do in a deal is seem desperate to make it.”

On the campaign trail, Donald Trump promised to bring the war in Ukraine to a close in 24 hours. After taking office, he amended that timeline to six months. Yet, he still espouses eagerness that borders on desperation, declaring on social media the need to “stop this ridiculous war” before more lives are lost and that “it is time to make a deal!” The White House’s message may resonate with many voters at home, but it reads as desperate to the Kremlin.

“The best thing you can do is deal from strength, and leverage is the biggest strength you have.”

In recent weeks, Trump has badly eroded U.S. leverage and climbed down from the position of strength.

He all but promised that the U.S. would stop supporting Ukraine financially and militarily unless compensated — and after the skirmish at the White House, Trump did suspend all military aid, to the tune of more than $1 billion. He also preemptively conceded three of Russia's key demands: no NATO membership for Ukraine, ever; no complete recovery of the territory seized by Russia; and a change of the government in Kyiv through a presidential election in wartime, contrary to Ukraine's constitution.

Trump has further undermined his negotiating position by seeking to delegitimize Zelensky’s leadership, which stunned the world by rebuffing the Russian military — once considered Europe’s most powerful — for three years. Bizarrely suggesting that Zelensky was to blame for the war, Trump baselessly accused him of profiting from the "gravy train" of U.S. assistance. While preparing to talk to the despot about to enter his 26th year in power, Trump repeated the Kremlin master’s charge of Zelensky’s being a "dictator" afraid of an election. At a 57 percent approval rating, Zelensky is way ahead of Trump and all but certain to win a free and fair election.

“Listen to your gut, no matter how good something sounds on paper.”

Putin lies, habitually and instinctively. He is perhaps no longer capable of distinguishing between falsehoods and the truth.

“We have not used our armed forces in Crimea,” Putin told the world in 2014 while the Russian spetznaz were occupying the Ukrainian peninsula. "There is absolutely no proof,” he said in 2019 in response to overwhelming evidence that a Russian missile shot down Malaysia Airlines flight 17, a civilian airliner, over eastern Ukraine. Russia’s military is “not a threat to any other country," Putin said at a press conference days before launching an all-out assault on Kyiv in 2022.

Having all but discarded the main protective layers in which any agreement with Putin’s Russia must be ensconced — key among them, continuing U.S. commitment to financial and military support and Ukraine’s place within the NATO defense perimeter, although not, at the moment, within the alliance itself — would Trump trust Putin’s signature on a piece of paper enough to hand the (very real) dictator a peace agreement with no enforcement? By giving up the leverage and the position of strength, isn't Trump making a choice for paper vs. the gut?

Putin equates respect with fear. Trump’s professed respect for Putin would buy the U.S. president zero reciprocity unless backed up by material force and effective action. Surely, his decades in real estate must have taught Trump this lesson. Would he forget it as he sits down with Putin in Riyadh, along with his other rules of the art of the deal?

Leon Aron is a senior fellow at the American Enterprise Institute. His most recent book is “Riding the Tiger: Vladimir Putin’s Russia and the Uses of War.” Brady Africk is deputy director of media relations and data design at AEI.

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