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All Eyes on Alaska: Why Trump is Hardly a Shrewd Negotiator

Although Trump holds a significantly stronger hand as leader of the free world, he squandered much of that leverage by showing how eager he is to make a deal and win the Nobel Peace prize.
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August 15, 2025
Andrew Harnik/Getty Images

President Trump likes to portray himself as a great dealmaker– a shrewd negotiator who knows how close the toughest deals.

But in reality, he’s more of an impulsive man who craves power and attention and flies by the seat of his pants.

And he’s meeting in Alaska today with a real shrewd negotiator in Russian President Vladimir Putin, as they confront one of the world’s toughest problems– the war in Ukraine.

Although Trump holds a significantly stronger hand as leader of the free world, he squandered much of that leverage by showing how eager he is to make a deal and win the Nobel Peace prize. Trump sees a unique opportunity to fix a high-profile global conflict and be seen as the world’s great peacemaker. That’s one hell of an incentive.

His cockiness knows no bounds. During the 2024 presidential election, Trump vowed that he would end the war in Ukraine in 24 hours—or even before taking office. After those targets were obviously missed, he began throwing out deadlines. His latest was on July 28, when he issued Putin a deadline of “10 or 12 days” to cease hostilities, and the following day, he narrowed that down: 10 days, or by August 8. On the day that the ultimatum ran out, Trump announced he’d meet Putin in person, despite no end to the violence.

As David Graham writes in The Atlantic, “For the Russian autocrat, this is a win in itself. Putin is a global pariah facing an international warrant for his arrest, but the United States is welcoming him to American soil for the first time since 2015.”

Putin will exploit Trump’s weakness. He’s already sent praise Trump’s way, saying the U.S. is making “energetic and sincere efforts” to end the conflict in Ukraine.

Putin is not just shrewd but ruthless. He knows there’s no deal to be had with Ukraine; his demands are a non-starter. So he’ll try to use the high-stakes summit with Trump to pivot to other areas that may help repair Russia’s status and frayed relationship with the U.S., like nuclear talks, trade and the end of sanctions. In return, knowing Trump’s eagerness to get a deal, he’ll appear to be “giving” something on Ukraine (maybe some nebulous, conditional language on a ceasefire or land swaps). His aim will be to get Trump to put pressure on Ukraine President Volodymyr Zelensky in any follow-up meeting.

In other words, resolving this conflict will be as messy and complicated as it gets, and no glamorous summit can hide that.

Trump’s first mistake was to allow his eagerness to be a peacemaker, not to mention his obsession to look like a winner, get the better of him. So he improvised a global summit that will only raise expectations and put more pressure on him to succeed. That’s in keeping with his supreme confidence that with all the power he yields, he’ll be able to use carrots and sticks to make a deal happen. If that doesn’t work, it’s possible he’ll call the meeting a failure and double down on sanctions, but my guess is that with the eyes of the world on him, he’ll probably spin things to make it look like he “won” something.

“All wars end eventually, and usually they end at the negotiating table,” David Sanger writes in The New York Times. “And, as in any negotiation, disagreements over goals, bitterness, betrayal and recriminations often arise. Each of those could manifest in Anchorage when President Trump and President Vladimir V. Putin meet.”

Indeed they could, so we never know what can happen. Trump loves to be unpredictable.

As far as reaching a deal, however, what we do know is that the ultimate carrot is in the hands of Putin, and it’s got the word Nobel on it.

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