Daily Market Mispricings: 2 Political Events Where We Disagree With Polymarket — May 25, 2026

TL;DRNaly’s biggest politics disagreement on May 25, 2026 is that Polymarket still prices May Trump calls to Vladimir Putin at 25c YES and to Volodymyr Zelenskyy at 17c YES, while we see fair value closer to 60c and 55c. The sharp reason is cadence: active U.S.-brokered war diplomacy usually compresses leader-to-leader contact into the final week, not away from it.

Key Takeaways

Polymarket still treats both May call contracts as likely NO outcomes, but Naly sees both as live YES setups.

The edge is mostly about process, not vibes: once Trump is publicly brokering ceasefires and prisoner swaps, leader calls become an operational tool.

The market appears to overweight the lack of a pre-announced calendar and underweight how quickly ad hoc diplomacy can materialize.

Both contracts remain open as of May 25, 2026, so the relevant window is the final six days of May, not the full month.

2 Mispricings at a Glance

Event Snapshot

Will Trump speak to Vladimir Putin in May?

YES Resolves May 31, 2026 Open 70/100 confidence

Polymarket Top Answer NO 75%

Naly Top Answer YES 60%

Max Payout if Correct +75c

0c 50c $1.00

Polymarket Naly

Why we disagree: The market prices silence, but ongoing ceasefire bargaining makes another direct Trump-Putin contact more likely than a static calendar suggests.

Event Snapshot

Will Trump speak to Volodymyr Zelenskyy in May?

YES Resolves May 31, 2026 Open 60/100 confidence

Polymarket Top Answer NO 83%

Naly Top Answer YES 55%

Max Payout if Correct +83c

0c 50c $1.00

Polymarket Naly

Why we disagree: The market discounts direct Trump-Zelenskyy follow-up, but renewed U.S. peace-format planning gives strong incentive for another call before month-end.

How to read this: Polymarket Top Answer and Naly Top Answer show the final answer each side sees as most likely. Max Payout if Correct shows the gross upside from the current quote to the $1 settlement if the selected contract side wins. The horizontal graph still shows where that selected side sits on a 0c to $1 range for Polymarket versus Naly.

Event 1

Will Trump speak to Vladimir Putin in May?

ForecastContract · YESResolves May 31, 2026Open70/100 confidence

+75c

Max Payout if Correct

Polymarket Top Answer NO 75%

Naly Top Answer YES 60%
Trade on Polymarket →

Polymarket’s quoted 25c refers to the current YES entry price for a $1 binary contract, which also implies roughly a 25% market probability that Trump speaks to Putin before May ends. Naly’s 60% estimate is the fair cents price on that same YES side, or about 60c fair value. That means the max payout if correct is 75c profit on a 25c YES entry, while the fair-value edge is 35c, not 75c.

Causal Chain

Cause Trump already used a direct April 29 phone call with Putin to discuss a possible Ukraine ceasefire, so the communication channel is proven, recent, and active.

↓

Effect Once a White House-led process produces a May 8 ceasefire and prisoner-swap framework, follow-up calls become a practical coordination mechanism rather than a symbolic extra.

↓

Projection With six days left in the month as of May 25, a fragile truce, compliance disputes, or negotiation reset can easily force another Trump-Putin conversation.

Key Factors

| Factor
▲ | Reuters reported Trump said on April 29 that he discussed a possible Ukraine ceasefire in a phone call with Putin.
▲ | Reuters also reported the April 29 conversation lasted more than 90 minutes, which suggests a real working line, not a one-off ceremonial touchpoint.
▲ | AP reported on May 8 that Trump said Putin agreed to his request for a three-day ceasefire and prisoner swap, confirming live U.S.-Russia crisis management.
▼ | Reuters reported on May 8 that Trump hoped the truce could be extended, which implies unresolved implementation risk and room for another direct conversation.
▼ | The market appears anchored to the absence of a publicly posted May call, but diplomacy at this level is often announced after it happens, not before.

Bayesian Calculation

Base rate: 25% from the market’s YES price.

Positive update: A direct April 29 Trump-Putin call on Ukraine and a May 8 U.S.-brokered ceasefire both raise the odds that the line is used again before May 31.

Negative update: There is still no publicly confirmed May Trump-Putin call as of May 25, and ceasefire management can run through aides.

Naly estimate: 60% YES, or a 60c fair price.

Alternative explanation: The market’s NO bias could still be rational if Trump deliberately delegates the next step to aides after extracting the symbolic win of a short truce. In that world, both sides preserve political flexibility by keeping any follow-up below leader level until June.

What Would Make Us Wrong

We are wrong if the ceasefire and prisoner-swap channel is already stable enough to be handled by negotiators, or if either side decides that another leader call carries more domestic political risk than diplomatic value in the final week of May.

Fresh Checks

Reuters via Defense News: Trump says he discussed a Ukraine ceasefire with Putin on April 29

AP: Trump says Russia and Ukraine agreed to his request for a three-day ceasefire and prisoner swap on May 8

Reuters syndication: Russia and Ukraine confirmed a U.S.-mediated three-day ceasefire

Event 2

Will Trump speak to Volodymyr Zelenskyy in May?

ForecastContract · YESResolves May 31, 2026Open60/100 confidence

+83c

Max Payout if Correct

Polymarket Top Answer NO 83%

Naly Top Answer YES 55%
Trade on Polymarket →

Polymarket’s quoted 17c refers to the current YES entry price for a $1 binary contract, so the market is implying only about a 17% chance that Trump speaks to Zelenskyy before May 31. Naly’s 55% estimate is the fair cents price on that same YES side, or about 55c fair value. The max payout if correct is 83c profit on a 17c YES entry, while the fair-value edge is 38c.

Causal Chain

Cause Trump and Zelenskyy already spoke by phone on February 25, so there is a recent precedent for direct contact inside the current peace process.

↓

Effect Reuters reported on May 22 that Zelenskyy expects new U.S. proposals on negotiation formats and the schedule of meetings, which usually requires top-level political alignment before public rollout.

↓

Projection If Washington wants to restart diplomacy before June, the cheapest way to do it is a short Trump-Zelenskyy call to define terms, reduce mistrust, and tee up the next round.

Key Factors

| Factor
▲ | Reuters reported on February 25 that Trump was holding a phone call with Zelenskyy, confirming that this channel is active in 2026, not hypothetical.
▲ | AP reported on May 8 that Zelenskyy confirmed Trump’s ceasefire request had produced a tangible prisoner-swap framework.
▲ | Reuters reported on May 22 that Zelenskyy is expecting U.S. proposals on meeting formats and scheduling, which is exactly the kind of moment that often triggers leader outreach.
▲ | The market seems to price the strained politics between Trump and Kyiv as if they block contact entirely, but tense relationships often generate more calls, not fewer, when negotiations are unstable.
▲ | The contract only needs one verified conversation before May 31, and the remaining calendar is still long enough for a crisis-driven call.

Bayesian Calculation

Base rate: 17% from the market’s YES price.

Positive update: The February 25 Trump-Zelenskyy call, May 8 U.S.-mediated ceasefire arrangement, and May 22 talk of new U.S. meeting formats all increase the chance of a follow-up call.

Negative update: No publicly confirmed May Trump-Zelenskyy call has surfaced as of May 25, and personal friction could delay direct leader contact.

Naly estimate: 55% YES, or a 55c fair price.

Alternative explanation: The market may be assuming that Washington prefers to work Zelenskyy through envoys because direct Trump involvement can create headline risk or expose unresolved disagreements on territory and concessions.

What Would Make Us Wrong

We are wrong if the White House sees more downside than upside in another direct Trump-Zelenskyy conversation this month, or if U.S. proposals on new peace-talk formats arrive through staff channels without needing leader-level buy-in first.

Fresh Checks

Reuters: Trump holding a phone call with Ukraine’s Zelenskyy on February 25

Reuters: Zelenskyy says he expects U.S. proposals on new formats for peace talks on May 22

AP: Trump says Russia and Ukraine agreed to his request for a three-day ceasefire and prisoner swap

Conclusion

The watchpoints into month-end are straightforward: any ceasefire-extension push, prisoner-swap friction, new U.S. peace-format proposal, or renewed Russian strikes could force rapid Trump outreach to either Putin or Zelenskyy. Because both contracts resolve on May 31, 2026, the key question is not whether relations are warm, but whether events create enough urgency for one more leader call in the final week.

Methodology

Naly starts with the live market price as a base rate, then updates it with fresh reporting, event timing, communication cadence, and incentive analysis. We care less about headline tone than about what decision-makers need to do next. Our long-run calibration and resolution history are tracked at /track-record.

Disclaimer

This article is analysis, not financial advice. Prediction markets can move on new facts, unclear resolution criteria, liquidity shocks, and delayed reporting. Fair-value estimates are probabilistic views, not certainties.