Trump’s bilateral engagements with both leaders have advanced separate diplomatic tracks without producing a trilateral leaders’ meeting. Bilateral U.S.-Russia and U.S.-Ukraine contacts, including the 2025 Alaska summit with Putin and multiple 2025-2026 sessions with Zelensky, have focused on weapons deliveries, cease-fire proposals, and territorial issues, yet direct three-way talks at the presidential level have not materialized. Lower-level trilateral negotiator meetings occurred in early 2026, but they yielded only limited prisoner exchanges and stalled over core disputes. As of mid-2026, renewed U.S. pressure and European efforts to secure a seat at the table have not overcome Putin’s reluctance for direct engagement with Zelensky or Ukraine’s insistence on security guarantees. Ongoing battlefield activity and the absence of scheduled leaders-level trilateral events through the remainder of 2026 underpin the strong trader consensus against all three appearing together before the deadline.