What's happened
On Oct. 14, Trump envoy Steve Witkoff coached Putin's aide Yuri Ushakov on how to flatter President Trump during a call, encouraging Putin to praise Trump's Gaza ceasefire efforts. This call preceded Trump's decision against arming Ukraine with Tomahawk missiles and influenced a controversial 28-point peace plan favoring Russia. Witkoff is now set to meet Putin to discuss a revised peace proposal.
What's behind the headline?
Strategic Diplomacy and Messaging
Witkoff’s coaching of Putin’s aide to flatter Trump reveals a calculated diplomatic strategy aimed at leveraging the U.S. president’s ego to facilitate dialogue. This approach underscores how personal diplomacy and image management remain central to high-stakes international negotiations.
The Peace Plan’s Controversial Foundations
The 28-point peace proposal, emerging from these talks, heavily favors Russia by demanding significant Ukrainian territorial concessions and a NATO non-alignment pledge. Witkoff’s acknowledgment that Donetsk and land swaps are necessary for peace signals U.S. acquiescence to Russian demands, raising questions about Ukraine’s sovereignty and the plan’s viability.
Timing and Political Calculations
The call’s timing—just before Zelensky’s White House visit and amid discussions of arming Ukraine with Tomahawks—suggests an attempt to preemptively shape U.S. policy. Trump’s subsequent rejection of missile support after the Putin call indicates the influence of Witkoff’s diplomacy.
Implications for the Conflict
While the revised peace plan reportedly incorporates more Ukrainian interests, Russia’s anticipated rejection implies continued conflict. Witkoff’s ongoing negotiations and planned meetings with Putin highlight persistent efforts but also the complexity and fragility of peace prospects.
Broader Impact
This episode illustrates the intricate interplay between diplomacy, military aid decisions, and peace negotiations. It also exposes internal U.S. divisions, with critics like Rep. Don Bacon condemning Witkoff’s perceived pro-Russian stance, reflecting broader geopolitical tensions.
Forecast
The peace process will likely remain contentious, with significant hurdles ahead. Witkoff’s role and Trump’s influence will be pivotal in shaping U.S. policy and the conflict’s trajectory, but without Russian concessions, a lasting settlement remains elusive.
What the papers say
Bloomberg’s release of the October 14 call transcript between Steve Witkoff and Yuri Ushakov provides the foundational insight into the diplomatic maneuvering behind the scenes. According to Bloomberg, Witkoff advised Ushakov to have Putin congratulate Trump on the Gaza ceasefire, stating, “I would make the call and just reiterate that you congratulate the president on this achievement... that you respect that he is a man of peace.” This framing was intended to set a positive tone for the subsequent Putin-Trump call on October 16, which Bloomberg reports influenced Trump’s decision against arming Ukraine with Tomahawk missiles.
The New York Post elaborates on Witkoff’s suggestion to emulate the Gaza peace plan with a 20-point proposal for Ukraine, highlighting his belief that territorial concessions, specifically involving Donetsk, were necessary. The Post notes that this approach shaped Trump’s controversial 28-point peace plan, which was widely criticized for favoring Russia.
The Independent and AP News emphasize the political sensitivity of Witkoff’s role, with AP quoting Trump defending Witkoff’s negotiations as “standard” dealmaking, while Nebraska Republican Rep. Don Bacon called for Witkoff’s dismissal, accusing him of favoring Russian interests.
Reuters reports that Witkoff is scheduled to meet Putin soon to discuss a revised peace plan, with Trump asserting that only a few points of disagreement remain. However, sources cited by the New York Post suggest Russia is poised to reject the revised proposal, indicating ongoing conflict.
The Moscow Times contextualizes the call as the origin of the Trump-endorsed peace plan, noting its controversial demands on Ukraine and the lack of clarity on how the transcript was obtained. This adds a layer of intrigue and underscores the delicate nature of the negotiations.
Together, these sources paint a picture of complex diplomacy where personal flattery, strategic messaging, and contentious peace proposals intersect, revealing the challenges
How we got here
The Russia-Ukraine war, ongoing since 2022, has seen multiple diplomatic efforts to end hostilities. Trump’s envoy Steve Witkoff engaged with Russian officials in October 2025 to broker peace, leveraging Trump's recent Gaza ceasefire success. This led to a Trump-endorsed peace plan requiring Ukraine to make territorial concessions, sparking debate over its fairness and feasibility.
Go deeper
- What are the key points of the Trump-endorsed peace plan?
- How did the Gaza ceasefire influence US-Russia diplomacy?
- What is the current status of peace negotiations between Russia and Ukraine?
More on these topics
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Vladimir Vladimirovich Putin is a Russian politician and former intelligence officer who has served as President of Russia since 2012, previously holding the position from 1999 until 2008.
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Donald John Trump is an American politician, media personality, and businessman who served as the 45th president of the United States from 2017 to 2021.
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Yuri Viktorovich Ushakov is a Russian and former Soviet diplomat who served as the Ambassador of Russia to the United States from 1998 until 2008. Since 2012, he has been an advisor to the President of Russia on foreign policy issues.
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Steven Charles Witkoff is an American real estate investor and landlord based in New York City, and founder of the Witkoff Group.
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Kirill A. Dmitriev is the CEO of the Russian Direct Investment Fund, a $10 billion sovereign wealth fund created by the Russian government to co-invest in the Russian economy alongside the sovereign wealth funds of other countries.