Trump meets with Putin by December 31?

Trump Says He Wants Another Summit — But the Last One Was the Hard Part Trump has floated another meeting with Putin, including a specific location that never materialized into a confirmed date, and that pattern — genuine stated interest without a locked-in follow-through — is exactly what keeps this contract below even odds. The mechanism here isn't skepticism about intent; Trump has repeatedly signaled desire for continued direct engagement with Putin, and both sides have incentive to keep high-level dialogue alive given the stakes around Ukraine and broader European security. The structural obstacle is that major head-of-state summits require alignment on substance, not just scheduling — a second meeting carries expectations of tangible progress, and convening without a clear deliverable risks looking like empty theater rather than diplomatic momentum. That's a higher bar than the first meeting cleared, which functioned partly as an initial establishing encounter. The counterargument for a real chance of a second meeting rests on exactly the dynamic already in motion: sustained diplomatic engagement around the war, continued phone contact between the two leaders, and Trump's own demonstrated willingness to pursue direct summitry even amid uncertain outcomes. If negotiations reach a point where a signing moment or major announcement would benefit from in-person theater, that creates a natural trigger for scheduling to move quickly. The structural case against assuming this happens easily is that plans for a specific follow-up location were floated and then didn't convert into an actual confirmed date, suggesting the diplomatic groundwork required to justify a second summit hasn't yet solidified. Leaders don't typically meet again quickly after a high-profile first encounter unless there's a substantive reason forcing the moment. If a second meeting does happen, it would likely signal genuine movement toward a negotiated framework on Ukraine, given that leader-level summits tend to cluster around moments of real diplomatic progress rather than routine check-ins. Bottom line: watch for any confirmed date or location announcement for a follow-up summit — real logistical commitment there, not further stated intent, is the signal that would move this meaningfully above its current minority-probability pricing.