Will Zelenskyy and Putin speak?

The core reason to keep the probability low is that this outcome requires several difficult things to happen in sequence: Putin has to decide to appear at the relevant summit or some other acceptable venue, Moscow has to soften or reverse its public rejection of the Miami setting, and both sides have to see enough political value in a direct encounter to overcome the security, legitimacy, and optics costs. Zelenskyy’s willingness is necessary, but it is not close to sufficient; the binding constraint is Moscow’s incentive structure, and there is currently no sign that Putin is preparing to grant Zelenskyy the kind of meeting that would carry real diplomatic symbolism. The long gap since their last in-person meeting also matters, because the relationship has become more constrained and more propagandistic, not less.

At the same time, this is not a pure zero. High-level war diplomacy can move quickly when battlefield conditions, external pressure, or a carefully chosen summit window create an opening, and the fact that Zelenskyy is publicly inviting the meeting creates a small path if Putin wants to test negotiations without fully conceding substance. The most plausible route is not a warmly announced bilateral summit, but a narrow, last-minute encounter on the sidelines of a larger event if attendance lines up and intermediaries can manage the optics. Even so, the Kremlin’s current posture is much more consistent with stalling or redirecting talks than with agreeing to a direct face-to-face meeting before the deadline.

Compared with the market price of 16% for Yes, I think the market is somewhat too optimistic, though not wildly so. The market is likely giving too much weight to the possibility that summit diplomacy can suddenly unlock a meeting, while underweighting the fact that Putin has not confirmed attendance and has already publicly rejected the proposed venue. My estimate is lower than the market because the base rate for a direct Zelenskyy-Putin meeting under active war conditions is extremely low, and the remaining time window is short enough that there is limited room for a slow diplomatic buildup.