Should Ukraine’s worst fears come to pass, Donald Trump will on Friday give away land in the negotiating chamber that Russia could not win by force of arms. The ghosts of Munich, Yalta and other sordid bargains ought to be stalking Alaska.
Alas, such diplomatic notorieties are unlikely to be in Trump’s mind at his summit with Vladimir Putin. His chief Russia envoy, Steve Witkoff, is too confused about battle lines in today’s Ukraine to find time to study what such summits did to the maps of yesteryear. We can be sure that Putin will not be similarly unburdened by history.
What has happened over the past seven months is history enough.
To recap, Trump came to office vowing an instant deal to end Russia’s war on Ukraine. Having repeatedly failed to get Putin to agree to a ceasefire, Trump lost patience last month and vowed economic warfare on Russia unless Putin changed course.
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By agreeing to meet in Alaska, Putin is apparently responding to Trump’s threats. In reality, he has not yet agreed to a ceasefire.
This does not amount to game, set and match for Putin. But he is starting the tournament with a free set to his name.
The most critical slice of history is Trump’s meeting with Putin in Helsinki in 2018. Then Trump appeared to side with Putin against his own intelligence agencies in accepting that Russia had not interfered in America’s 2016 election.
To underline the point, Trump also revived a plan for a joint US-Russia cyber security taskforce that would focus on election integrity. That was like putting a wolf in charge of sheep welfare. Such was the US domestic outrage that Trump was forced to drop the idea.
But Trump is in a far stronger domestic position than he was in 2018. Dan Coats, then director of national intelligence, publicly defended the US intelligence agencies after Helsinki. Trump’s current director of national intelligence, Tulsi Gabbard, is radically different. She recently said that there had indeed been a Russia-related 2016 election plot, only it was cooked up by Barack Obama and his deep state to try to stop Trump from taking office.
It is beyond unlikely that any jury would convict Obama, Joe Biden or other “conspirators” of such an outlandish charge. But Gabbard did what was required of her, which was to deflect from the controversy over Trump’s refusal to release the Jeffrey Epstein files.
None of which necessarily means that Trump will cave in to Putin. The Russian leader still has to persuade the US president to read Ukraine’s map the way he does. Putin has delayed potentially crippling US sanctions on Russia’s oil exports, which have been keeping Russia’s economy afloat. But Trump’s threat is only suspended.
Putin has already crossed one line with Trump that, for others, would earn banishment – Trump’s humiliation. Almost every time the US president has asked Putin for a ceasefire, Russia’s attacks on Ukraine have intensified the next day. This hurt Trump’s vanity and led to his reversal of the Pentagon’s ban on selling arms to Ukraine.
Against that are two things in Putin’s favour that are of existential concern to Ukraine. The first is the fact that Trump wants a deal far more than Putin. Russia has suffered more deaths in Ukraine than in every Soviet and Russian war combined since 1945.
Although Russia has lost some of the Ukrainian territory it seized following its February 2022 invasion, Putin believes time is on his side.
Should he exploit Trump’s desire for a deal to win territory that Ukraine has lost so much blood defending, the backlash would be furious. Ukraine’s Volodymyr Zelenskiy would be ejected from office were he to agree to any uneven land swaps. Trump’s infamous upbraiding of Zelenskiy in their February Oval Office encounter was a moment of truth. “You don’t have the cards,” Trump said.
Putin’s second advantage is Trump’s ignorance. In addition to Winston Churchill, Franklin Roosevelt had Harry Hopkins at Yalta, yet Joseph Stalin still got what he wanted. Trump has Witkoff. After Witkoff’s first meeting with Putin in March, Trump’s envoy did not know which Ukrainian oblasts Putin claims sovereignty over. Five months later Witkoff still seems confused. Deal making bluster is no substitute for knowledge.
Theodore Roosevelt famously said that US presidents should speak softly and carry a big stick. Trump has been talking loudly and wielding a noodle. Putin has good reasons to be hopeful on Friday.
– Copyright The Financial Times Limited 2025
