Trump’s Envoy Third Meeting with Putin: Ukraine Negotiations at Critical Juncture

As the Ukraine war enters its third year, former President Trump’s special envoy Steve Witkoff has held another meeting with Russian President Vladimir Putin, marking their third high-level contact this year. This series of intensive diplomatic activities suggests that while public statements remain cautious, backchannel communications are accelerating behind the scenes.

The “Parallel Diplomacy” of Trump’s Team

The very role of Witkoff—a real estate mogul turned unconventional diplomat—is intriguing in itself. Representing neither the current Biden administration nor fully belonging to Trump’s campaign team, his ambiguous status creates unique space for U.S.-Russia communication. From my observation, this “unofficial channel” approach reflects Trump’s characteristic “art of the deal” mentality—bypassing bureaucratic systems to engage directly with decision-makers.

Notably, Witkoff previously suggested transferring “ownership” of four eastern Ukrainian regions to Moscow in exchange for a ceasefire. This highly controversial proposal caused uproar in American political circles but reveals the potential realist approach of Trump’s team. In my view, while politically incorrect, this “land for peace” thinking mirrors the genuine war fatigue among segments of the U.S. elite.

The Kremlin’s “Two-Track Strategy”

Putin’s reception of Trump’s envoy is equally noteworthy. While maintaining military pressure on the battlefield, Russia appears open to negotiations—this dual strategy suggests the Kremlin is preparing for various scenarios. My analysis indicates Putin likely aims to influence the U.S. pre-election political climate through engagement with Trump’s team while laying groundwork for potential administration changes.

Kremlin spokesman Peskov’s deliberate downplaying of expectations—”no breakthrough anticipated”—is classic diplomatic rhetoric. Historical patterns show that the more significant the negotiations, the more expectations are managed downward beforehand. I believe Russia’s current priority is probing the Trump team’s true positions while establishing communication channels ahead of a possible Republican administration.

Ukraine’s Dilemma and Choices

Amid diplomatic efforts, battlefield conditions remain severe. Data shows that since Kyiv’s March 11 ceasefire proposal, Russian forces have launched 70 missiles and 2,200 drones at Ukraine. This combination of military pressure and diplomatic outreach leaves Ukraine torn between war and peace.

From my years observing Eastern European affairs, President Zelensky’s government faces triple pressures: unpredictability of Western aid, worsening battlefield dynamics, and domestic political divisions. Particularly during a U.S. election year, Ukraine must account for potential policy shifts should Trump return. Evidence suggests Kyiv is adjusting its strategic communications to prepare for various scenarios.

Policy Struggles Within America

The Biden administration publicly supports Ukraine’s “territorial integrity” stance while tacitly permitting Trump team’s diplomatic outreach—this contradictory posture reflects deeper divisions in U.S. Ukraine policy. From my understanding, realist voices advocating “swift war termination” do exist within Washington’s foreign policy circles, but political correctness prevents open expression.

Particularly noteworthy is Trump’s social media statement urging Russia to “make a move” to end the war. This direct engagement with adversaries breaks many diplomatic taboos. I believe this foreshadows potential major adjustments in U.S. Russia policy under a possible second Trump term—shifting from ideological confrontation to more transactional relations.

Looking Ahead: Pathways to Peace?

Synthesizing available information, I foresee three potential scenarios for Ukraine peace efforts in coming months:

  1. Status Quo: Until the U.S. election, parties maintain current positions, battlefield stalemate continues, and diplomatic contacts proceed without substantive breakthroughs.
  2. Partial Progress: Limited ceasefire agreements reached at international forums (e.g., G20), creating conditions for further talks.
  3. Strategic Shift: U.S. election results trigger policy upheaval, leading to major diplomatic breakthroughs or military escalation.

Current dynamics favor the first scenario, but all sides are preparing for the latter two. Especially significant are Trump team’s diplomatic activities potentially laying groundwork for future negotiation frameworks.

Personal Perspective: Peace Requires Mutual Compromise

Drawing on years studying international conflicts, I believe the Ukraine war will ultimately be resolved through negotiations rather than military means. History shows most prolonged wars end with some form of political compromise. The question isn’t whether to negotiate, but when and under what terms.

The key challenge facing the international community is balancing defense of international order principles with acknowledgment of geopolitical realities. Total adherence to either extreme risks prolonging conflict. Genuine peace requires painful but necessary compromises from all sides—Ukraine may need to accept territorial losses, Russia must abandon expansionist ambitions, and the West should reconsider its security architecture.

While controversial, the Trump team’s diplomatic outreach at least offers fresh thinking for breaking the current deadlock. With the war’s catastrophic humanitarian toll, any effort promoting dialogue deserves serious consideration.

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