Trump’s Deal-making Could Hand Putin a Win at Ukraine’s Expense
WHO:
CNN - President Trump’s special envoy Steve Witkoff met with Russian President Vladimir Putin in St. Petersburg. CNN described Witkoff as Trump’s business associate-turned-top negotiator.
CNN - Other participants in the peace discussions included Ukrainian President Volodymyr Zelensky and officials from the United States, Europe, and NATO.
CNN - Kiril Dmitriev, head of Russia’s sovereign wealth fund and a key Kremlin interlocutor with Trump administration officials, discussed proposed economic projects.
CNN - Stephen Hubbard, a 74-year-old US citizen originally from Michigan, had been held in Russia after being captured in Ukraine.
Robert Reich | Substack - Trump, Elon Musk, and Russian President Vladimir Putin are discussed in connection with decisions affecting Ukraine. Robert Reich said he consulted Trump-watchers and Russian experts.
Robert Reich | Substack - Trump said, “Russia, frankly, has been fine on Ukraine,” and, “We’ve given a lot to Ukraine. They’ve given nothing to us.”
WHAT:
CNN - Witkoff and Putin held three hours of talks. A US official said Witkoff was in Russia to “test” whether a new peace plan could provide a basis for peace talks.
CNN - Putin said he was “curious” about the outcome of discussions in Norway involving US, European, and NATO officials and Zelensky. A Kremlin aide said those discussions “contained little of actual value for resolving the Ukrainian crisis.”
CNN - Russia’s stated demands include control over all of eastern Ukraine’s Donbas region and influence over Kyiv’s future security arrangements.
CNN - Trump lifted sanctions on Russian diesel exports and announced an energy ceasefire proposal that would have required Ukraine to stop drone strikes on Russian oil refineries. The article says the proposal was unsuccessful.
CNN - Trump called for a change in Ukraine’s leadership. The article says US intelligence sharing was affected amid the disputes.
CNN - Putin proposed increasing Russian fertilizer exports to the United States. Dmitriev said the sides also discussed data centers and energy projects and cooperation.
CNN - Russia released Hubbard before the meeting. Witkoff called the release “a humanitarian”; the White House presented it as evidence of Trump’s deal-making, and Trump’s Truth Social statement said the United States “was not required to give anything in return.”
Robert Reich | Substack - Reich said Trump or Musk, or both, slowed or eliminated Ukraine’s access to Starlink satellite intelligence, leaving Ukraine without warning of Russian bombs. Reich also said Trump pushed Ukraine to capitulate and called for a “new president.”
Robert Reich | Substack - Reich said Trump lifted sanctions on Russian oil sales, made a deal for the United States to buy Russian diesel, and declined to impose additional Russia sanctions authorized by the Lindsey Graham Act.
Robert Reich | Substack - Reich said Trump invited Putin to the G20 summit in Miami and accepted Putin’s invitation to a three-way summit with Chinese leader Xi to decide Ukraine’s fate.
WHERE:
CNN - Witkoff and Putin met in St. Petersburg, Russia; the peace-plan discussions took place in Norway.
CNN - Hubbard was held in a remote Russian penal colony after being captured in Ukraine.
Robert Reich | Substack - Reich said the G20 summit Trump invited Putin to was to be held in Miami.
WHEN:
CNN - Hubbard had been held since his capture in Ukraine in 2022; the article describes his captivity as four years.
Robert Reich | Substack - Reich said Trump declined additional sanctions two days before they were due to take effect and invited Putin to the G20 summit in December.
WHY:
CNN - CNN said Trump lifted Russian diesel sanctions in a politically driven effort to ease US fuel prices ahead of midterm elections, while also providing an economic benefit to Moscow.
CNN - CNN said the Kremlin viewed US concessions and economic incentives as signs its strategy was working, rather than reasons to compromise.
Robert Reich | Substack - Reich framed his article around asking why Trump was apparently “selling out Ukraine”; he presented several explanations from Trump-watchers and Russian experts.
(UPDATED October 21, 2026 19:25 UTC)
President Trump’s envoy Steve Witkoff met Russian President Vladimir Putin for three hours in St. Petersburg, testing whether a new peace plan could lead to talks on Ukraine. The discussions followed a meeting in Norway among Ukrainian President Volodymyr Zelensky and US, European, and NATO officials. Putin said he was curious about that meeting, while a Kremlin aide dismissed its value. Russia is demanding control of all the Donbas and influence over Ukraine’s future security arrangements. Trump has lifted sanctions on Russian diesel and proposed an energy ceasefire that would have halted Ukrainian drone strikes on Russian oil refineries; the proposal failed. Moscow also discussed fertilizer, data centers, and energy projects with Witkoff’s delegation. Before the meeting, Russia released US citizen Stephen Hubbard, held since his capture in Ukraine in 2022. Witkoff called the release humanitarian, and Trump said the United States gave nothing in return.