Daily Market Mispricings: 2 Events Where We Disagree With Polymarket — May 8, 2026

TL;DRNaly disagrees most with Polymarket on Steve Witkoff meeting Iran by May 31 and on a June 30 Hormuz blockade-lift announcement. We price Witkoff YES at 65c versus the market's 41c, and blockade-lift YES at just 48c versus 73c. The sharpest reason: traders are overpaying for headlines while underpricing the exact contract mechanics that determine whether talks or de-escalation actually count.

Key Takeaways

The clearest answer flip is Steve Witkoff's May 31 Iran-meeting contract: Polymarket still leans NO 59%, while Naly makes YES the favorite at 65%.

The June 30 Hormuz blockade contract looks too optimistic because resumed shipping or a paused naval operation do not count unless Washington explicitly announces the blockade has ended.

Both disagreements are really contract-mechanics calls: one market may be underpricing how many qualifying meeting paths still exist, while the other may be overpricing how quickly diplomacy turns into a formal public lift statement.

2 Mispricings at a Glance

Event Snapshot

Will Steve Witkoff have a diplomatic meeting with Iran by May 31?

YES Resolves May 31, 2026 Open High confidence

Polymarket Top Answer NO 59%

Naly Top Answer YES 65%

Max Payout if Correct +59c

0c 50c $1.00

Polymarket Naly

Why we disagree: The market still prices the absence of a confirmed date too heavily even though Witkoff is already one of the principals on the live MOU track.

Event Snapshot

Will Donald Trump announce that the United States blockade of the Strait of Hormuz has been lifted by June 30, 2026?

YES Resolves June 30, 2026 Open Medium-High confidence

Polymarket Top Answer YES 73%

Naly Top Answer NO 52%

Max Payout if Correct +27c

0c 50c $1.00

Polymarket Naly

Why we disagree: The market is pricing a diplomatic glidepath, but the contract needs an explicit lift announcement and Washington keeps separating de-escalation from formally ending the blockade.

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 Steve Witkoff have a diplomatic meeting with Iran by May 31?

GeopoliticsContract · YESResolves May 31, 2026OpenHigh confidence

+59c

Max Payout if Correct

Polymarket Top Answer NO 59%

Naly Top Answer YES 65%
Trade on Polymarket →

The quoted line here is 41c on YES, meaning a buyer pays 41 cents for a binary claim that returns $1 if Steve Witkoff is physically present and actively negotiating in a qualifying U.S.-Iran diplomatic meeting by May 31, 2026. Our separate probability estimate is 65% YES, which implies a 65c fair price on that same YES leg. This is a real answer flip, not just a confidence tweak: Polymarket's top answer is NO 59%, while Naly makes YES the favorite. Buying YES at 41c offers a max payout if correct of 59c, while the fair-value edge is +24c because our fair price is materially higher than the entry price.

Causal Chain

Cause Cause: On May 6, 2026, Axios reported that a 14-point U.S.-Iran memorandum is being negotiated by Steve Witkoff and Jared Kushner with Iranian officials, both directly and through mediators.

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Effect Effect: Once Witkoff is already one of the live principals on the war-ending track, the odds of at least one qualifying in-person meeting before May 31, 2026 rise materially above a simple "no date on the calendar" reading.

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Projection Projection: The likeliest path is a Pakistan- or Geneva-based negotiating session tied to the next response cycle on the draft framework, which makes a single qualifying Witkoff appearance more likely than the market's 41c YES price implies.

Key Factors

| Factor
▲ | On May 6, 2026, Axios reported that the White House believed it was the closest the parties had been to an agreement since the war began and that the next 48 hours were critical for Iranian responses.
▲ | The same report said negotiations could happen in Islamabad or Geneva, which matters because the contract only needs one qualifying in-person diplomatic meeting, not a final peace deal.
▲ | On May 6, 2026, Trump said the U.S. and Iran had "good talks over the last 24 hours," signaling that the channel is live rather than frozen.
▲ | Polymarket's own contract framing requires Witkoff to be physically present and actively participating as a negotiator; that is a narrower bar than "peace deal signed" but a wider path than traders often assume when they focus only on headline summits.
▼ | The main bearish fact is still process uncertainty: Trump canceled one Pakistan trip on April 25, 2026, and Tehran has been slow-walking responses through Pakistani mediators.

Bayesian Calculation

Base rate: 41% YES from our May 8, 2026 selection snapshot.

Positive update: Witkoff is named as an active negotiator on the current MOU, venue options are already circulating, and Washington wants a breakthrough before Trump's China trip concludes.

Negative update: No public meeting date is locked, Iran may prefer mediator-only exchanges, and a single hardline objection in Tehran could delay an in-person session past May 31, 2026.

Naly estimate: 65% YES, which makes YES the favorite and flips the market's current NO-leaning top answer.

Alternative explanation: The market may simply be pricing calendar friction correctly: if the White House keeps negotiating through paper exchanges and phone relays, Witkoff can remain central to diplomacy without ever appearing in a qualifying in-person session before the deadline.

What Would Make Us Wrong

A fresh cancellation of travel, an Iranian refusal to meet U.S. envoys face-to-face, or a switch to lower-level technical talks would all cut off the easiest YES paths and likely justify Polymarket's current NO lead.

Fresh Checks

Axios: U.S. and Iran closing in on one-page memo to end war, officials say

Axios: Trump optimistic as U.S. awaits Iran's response to peace framework

AP: Trump dispatches Witkoff and Kushner to Pakistan for new talks with Iran's foreign minister

Polymarket: Will Steve Witkoff have a diplomatic meeting with Iran by May 31?

Event 2

Will Donald Trump announce that the United States blockade of the Strait of Hormuz has been lifted by June 30, 2026?

ForecastContract · YESResolves June 30, 2026OpenMedium-High confidence

+27c

Max Payout if Correct

Polymarket Top Answer YES 73%

Naly Top Answer NO 52%
Trade on Polymarket →

The quoted line here is 73c on YES, so a trader pays 73 cents for a binary contract that returns $1 if Trump, the U.S. government, or the U.S. military explicitly announces that the blockade has been lifted by June 30, 2026. Our separate estimate is 48% YES, which implies a 48c fair price on that same YES leg. This is another answer flip: Polymarket makes YES the favorite at 73%, while Naly makes NO the slight favorite at 52%. At 73c YES, the max payout if correct is only 27c, and the fair-value edge on buying that YES is -25c because our fair price is below the entry price.

Causal Chain

Cause Cause: The market is blending three different things into one price: partial shipping normalization, a paused U.S. naval operation, and a formal public announcement that the blockade has ended.

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Effect Effect: That bundling overstates YES because the contract only resolves on explicit lift language, and Washington has repeatedly said the blockade remains in full force even while exploring narrower de-escalation steps.

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Projection Projection: Unless a signed framework includes unmistakable wording that the blockade has ended or will end on a named date, the contract can still fail even if ships move and fighting cools before June 30, 2026.

Key Factors

| Factor
▲ | Polymarket's own rules say resumed shipping or behavior merely inconsistent with a blockade is not enough; there must be a clear public statement that the blockade has lifted, ended, or will end on a specified date.
▲ | On May 5, 2026, Trump paused Project Freedom but said the blockade would remain in full force while negotiators tried to finalize an agreement.
▲ | Reuters reported on May 2, 2026 that an Iranian proposal would reopen the strait and end the U.S. blockade while postponing nuclear talks, which is the core bullish path for YES.
▲ | But on May 7, 2026, Axios and AP both reported fresh U.S.-Iran fire exchanges around the strait, which raises the political cost of making a clean lift announcement soon after new attacks.
▲ | Reuters reported on May 4, 2026 that the U.S. was still intercepting missiles and drones while describing the blockade as exceeding expectations, showing the blockade remains an active leverage tool rather than a box already checked for removal.

Bayesian Calculation

Base rate: 73% YES from our May 8, 2026 selection snapshot.

Positive update: The live MOU track reportedly contemplates lifting restrictions around transit through the Strait of Hormuz, and an eventual peace framework could include a formal blockade end date.

Negative update: Official statements keep distinguishing between opening shipping lanes and lifting the blockade, and renewed fighting makes a definitive public lift announcement less automatic than the market suggests.

Naly estimate: 48% YES, which means NO 52% becomes our top answer despite a still-real diplomatic path to a June announcement.

Alternative explanation: The market may be right if the White House wants a visible peace dividend before July 2026 and packages a ceasefire extension, sanctions framework, and blockade-lift date into one public announcement from Trump or the State Department.

What Would Make Us Wrong

A signed one-page framework that explicitly says the blockade is lifted immediately or on a named date, plus follow-through from Trump or another qualifying U.S. channel, would quickly move this contract toward the market's current YES view.

Fresh Checks

Polymarket: Will Donald Trump announce that the United States blockade of the Strait of Hormuz has been lifted by June 30, 2026?

Axios: Trump suspends Hormuz operation, claims progress on Iran deal

Reuters via Investing: Trump says operation to reopen Strait of Hormuz will be paused

AP: US military says it intercepted Iranian attacks on 3 Navy ships in Strait of Hormuz

Conclusion

The next real catalysts are not vague optimism posts. For the Witkoff contract, watch for a publicly reported Islamabad or Geneva session with Witkoff physically in the room. For the Hormuz contract, watch for exact wording from Trump, the State Department, or the Pentagon that the blockade has ended or will end on a stated date. Until those two concrete signals appear, we think Polymarket is underpricing one meeting and overpricing one announcement.

FAQ

Why is the Witkoff market an answer flip instead of a confidence disagreement?

Because Polymarket's top answer is still NO 59%, while Naly makes YES 65% on the same contract. We are not just saying YES is cheap; we are saying YES should be the favorite.

Why is Naly below market on the Hormuz blockade contract even though talks are active?

Because active talks, resumed shipping, or a paused escort mission do not resolve this market. The contract needs a public U.S. announcement explicitly ending the blockade, and Washington keeps saying the blockade remains in force.

What does a price like 41c YES or 73c YES actually mean?

It means you pay that many cents for a $1 binary claim on the named YES outcome. A 41c YES quote implies roughly a 41% market probability on YES, and a Naly estimate of 65% YES implies a 65c fair price on that same YES leg.

Methodology

We start from market-implied priors, update with fresh reporting, and then translate our final probability back into a fair cents price on the same contract side. We also separate contract mechanics from narrative momentum, because markets often overreact to headlines that do not actually satisfy resolution wording. Our calibration, wins, misses, and confidence discipline live on Naly's track record.

Disclaimer

This is probabilistic research for informational purposes only, not investment advice or a solicitation to trade. Prediction markets can move on new facts, contract clarifications, and liquidity shifts, and our fair values can change as the evidence changes.