Camilla Jessen
From Clinton to Trump, every U.S. president has believed they could strike a new deal with Russia. Time and again, Vladimir Putin has proven them wrong.
U.S. President Donald Trump is finding it more difficult than expected to secure a peace deal with Russian President Vladimir Putin over the war in Ukraine, CNN reported on Saturday.
Despite several phone calls between Trump and Putin and multiple visits to Moscow by U.S. envoy Steve Witkoff, no agreement has been reached.
Witkoff, a real estate businessman with no previous diplomatic experience, returned from his latest trip with little progress, according to officials familiar with the talks.
The U.S. proposal reportedly includes recognition of Russia’s control over Crimea — a major sticking point for Ukraine, which has repeatedly said it will not cede any territory.
I would say the negotiations are going very well — from Putin’s point of view,” Angela Stent, a former national intelligence officer for Russia and Eurasia, told CNN. “He has no intention of stopping the war but benefits from restoring diplomatic ties with the U.S.
Experts say Putin is stalling, believing time is on Russia’s side and that Ukraine, with pressure from its Western allies, may eventually accept a deal more favorable to Moscow.
Classic Russian Tactics
Delaying negotiations, avoiding direct refusals, and negotiating small details are long-standing Russian tactics, analysts say. Such strategies have been seen before, including during Syria ceasefire talks.
It remains unclear if the Trump administration underestimated these tactics or chose to engage despite them. Trump has often expressed a view of world affairs similar to Putin’s, seeing global power dominated by major nations, experts noted.
“Trump talks about great power competition, suggesting that big powers can take over smaller ones, and from Putin’s point of view, that’s fine,” Stent said.
Trump has shown little long-term interest in Ukraine’s future, at one point suggesting Ukraine “could be Russia one day,” CNN reported.
If negotiations continue to stall, Trump could use this as justification to withdraw U.S. involvement.
Putin’s Negotiating Style
Putin’s background in the KGB influences his approach to diplomacy, experts say. He prepares thoroughly, uses charm and intimidation, and keeps counterparts off balance. His tactics include keeping leaders waiting, creating confusion, and using symbolic gestures to show dominance.
In 2018, during a summit in Helsinki, Putin handed Trump a World Cup soccer ball, saying “the ball is in your court,” a move interpreted as a calculated gesture aimed at appealing to Trump’s ego.
Putin has outlasted several American presidents and is familiar with handling Western leaders. By contrast, the current U.S. negotiating team, including Secretary of State Marco Rubio and National Security Advisor Mike Waltz, lacks significant experience dealing with Russia, experts say.
Meanwhile, Russia’s delegation includes seasoned diplomats such as Foreign Minister Sergei Lavrov and former ambassador Yuri Ushakov.
Possible U.S. Shift
Trump’s administration could soon shift its approach. Rubio recently suggested that the U.S. might abandon its efforts if progress is not made within days. CNN also reported growing frustration inside the White House over the lack of breakthroughs.
“The Trump administration is eager for a deal but unwilling to offer major concessions, such as U.S. security guarantees or more military aid to Ukraine,” said Jennifer Kavanagh of Defense Priorities, a think tank advocating for a restrained U.S. foreign policy.
For Trump, stabilizing relations with Russia may be more important than reaching a full peace settlement, Kavanagh said.
Historical Patterns
Trump is not the first American president to believe he could improve relations with Russia. Experts say each administration has tried — and failed — to “reset” ties.
George W. Bush once said he “looked into Putin’s eyes and felt his soul,” but relations quickly deteriorated. Other efforts, such as Russia’s admission into the G7 under President Bill Clinton and joining the World Trade Organization under President Barack Obama, also failed to bridge deeper divisions.
Analysts argue that U.S. leaders have often underestimated how differently Russia views the world.
Russia sees Western unity as a threat,” said Sam Greene of the Center for European Policy Analysis. “Most U.S. administrations have not understood how deep Russia’s shift toward authoritarianism and confrontation with the West has been.
Thomas Graham, a former senior director for Russia on the U.S. National Security Council, said it was always unrealistic to expect a broad partnership with Russia after the Cold War.
“Given Russia’s interests and history, that was never really possible,” Graham said.
He suggested that the best outcome would be a relationship of “competitive coexistence,” where rivalry stays mainly in political and economic areas rather than military conflict.
Russia, Graham and others warned, is not going away. It will remain a key player in European security and a competitor to Western power for the foreseeable future.