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Trump’s Team Gives Putin ‘How to Approach the President’ Coaching

Steve Witkoff, Trump’s special envoy, provided Kremlin aide Yuri Ushakov with detailed guidance on how Putin should communicate with the U.S. president, offering what amounts to diplomatic “coaching” ahead of critical Ukraine discussions.

November 26, 2025Clash Report

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According to Bloomberg, in the October 14 conversation, Witkoff outlined not only the content of the peace plan but also detailed tactical suggestions on which statements would appeal to Trump. He highlighted the Gaza peace deal as a reference point and suggested that Putin praise Trump as a “man of peace” to advance negotiations.

“Congratulate Him, Emphasize His Role as a Peace-Maker”

Phone recordings reveal that Witkoff instructed Ushakov on the types of messages Trump prefers. Witkoff suggested that Putin congratulate Trump for the Gaza agreement and describe him as a “true man of peace,” which would soften the conversation and create a more favorable atmosphere for the Ukraine plan.

Ushakov reportedly welcomed these recommendations and confirmed that Putin would use this messaging.

From 20 Points to 28 Points: The Peace Draft Takes Shape

Witkoff mentioned that Trump’s team had prepared a 20-point peace framework, which could be adapted jointly with Russia. This conversation appears to have laid the groundwork for the later 28-point plan that became public.

Putin later stated that the plan could serve as a foundation for peace. Trump confirmed on Truth Social that the draft was “almost finalized” and instructed Witkoff to meet Putin in person.

Timing Strategy Ahead of Zelenskiy’s Visit

One of Witkoff’s key recommendations was timing. He suggested that Putin speak with Trump before Zelenskiy’s October 17 White House visit, creating a strategic advantage for Russia to present its position.

The impact was immediate: Putin called Trump two days later, in a session lasting two and a half hours. Trump described the discussion as “very productive.”

Miami Meetings and Internal Kremlin Negotiations

After the call, Witkoff met with another senior Kremlin official, Kirill Dmitriev, in Miami for three days of follow-up talks. Meanwhile, Dmitriev and Ushakov discussed the “maximum demand” strategy, reflecting concerns that the U.S. might alter Russian proposals while claiming mutual agreement.

Pressure on Ukraine: Intelligence as Leverage

According to reports, the U.S. pressured Ukraine to accept the 28-point draft and even implied cutting critical intelligence support if Kyiv refused. Zelenskiy’s administration partially eased this pressure after discussions with Secretary of State Marco Rubio.

Proposed Territorial Arrangements: Donbas, Crimea, and Herson

The initial U.S. draft included:

  • Withdrawal of Ukrainian troops from areas of Donbas Russia failed to seize
  • Conversion of these areas into a neutral, internationally monitored buffer zone
  • Recognition of Russia’s de facto control over Crimea, Luhansk, and Donetsk
  • Freezing most remaining frontlines, including Herson and Zaporizhzhia

Ukraine and European allies insisted that hostilities cease along current lines.

“The President Gave Me Wide Latitude”

Witkoff told Ushakov that Trump granted him broad authority and suggested that creating a joint opportunity could lead to “major breakthroughs” in the peace process.