Daily Market Mispricings: 3 Events Where We Disagree With Polymarket — May 11, 2026

TL;DROn May 11, 2026, Naly’s clearest disagreements are Jerome Powell’s Fed-chair exit and another U.S.-Iran diplomatic meeting: Polymarket prices Powell-out-by-May-15 YES at 28c and U.S.-Iran-meeting-by-May-31 YES at 30c, where the market still leans No, while we mark them 84c and 68c fair. The sharpest reason is that traders are underweighting hard process timelines already forcing decisions.

Key Takeaways

Jerome Powell out as Fed Chair by May 15, 2026? is our strongest answer flip because the legal term-end date and Warsh confirmation path matter more than the market’s inertia bias.

US x Iran diplomatic meeting by May 31, 2026? looks underpriced because the channel is still active even after Trump rejected Tehran’s latest response.

MicroStrategy sells any Bitcoin by June 30, 2026? is the reverse setup: the market is too eager to extrapolate one striking comment into an actual sale.

The core edge across all three markets is causal sequencing: deadlines, financing options, and mediator incentives matter more than headline tone.

3 Mispricings at a Glance

Event Snapshot

Jerome Powell out as Fed Chair by May 15, 2026?

YES Resolves May 15, 2026 Open High confidence

Polymarket Top Answer NO 72%

Naly Top Answer YES 84%

Max Payout if Correct +72c

0c 50c $1.00

Polymarket Naly

Why we disagree: The market is underweighting the hard chair-term expiry and the cleaner confirmation path for Kevin Warsh.

Event Snapshot

US x Iran diplomatic meeting by May 31, 2026?

YES Resolves May 31, 2026 Open Medium-High confidence

Polymarket Top Answer NO 70%

Naly Top Answer YES 68%

Max Payout if Correct +70c

0c 50c $1.00

Polymarket Naly

Why we disagree: Traders are overreacting to one rejection even though Pakistan-backed diplomacy is still active and another meeting is easier than a full peace deal.

Event Snapshot

MicroStrategy sells any Bitcoin by June 30, 2026?

YES Resolves June 30, 2026 Open Medium confidence

Polymarket Top Answer YES 67%

Naly Top Answer NO 58%

Max Payout if Correct +33c

0c 50c $1.00

Polymarket Naly

Why we disagree: The market is treating management’s new willingness to sell as if an actual sale is now more likely than not, despite ample financing alternatives.

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

Jerome Powell out as Fed Chair by May 15, 2026?

ForecastContract · YESResolves May 15, 2026OpenHigh confidence

+72c

Max Payout if Correct

Polymarket Top Answer NO 72%

Naly Top Answer YES 84%
Trade on Polymarket →

The market is underweighting the hard chair-term expiry and the cleaner confirmation path for Kevin Warsh.

Causal Chain

Cause Cause: Powell’s second chair term has an official May 15, 2026 end date, and the succession process is no longer blocked by the Justice Department probe that had slowed Kevin Warsh.

↓

Effect Effect: Once the legal and political bottlenecks eased, the relevant probability stopped being “can Trump replace Powell eventually?” and became “does anything concrete still prevent the handoff on time?”

↓

Projection Projection: Barring a last-minute Senate slip or contract-resolution ambiguity around a pro tem bridge, the path of least resistance is Powell no longer being chair by the deadline.

Key Factors

| Factor
▲ | The Federal Reserve’s own 2022 swearing-in release still says Powell’s chair term ends on May 15, 2026, which makes the calendar itself a real catalyst rather than a narrative talking point.
▲ | Powell said on April 29 that he would remain on the Board as a governor for a period of time, but that there is only one chair and Warsh becomes that chair when he is confirmed and sworn in.
▲ | Reuters reported on April 24 that the Justice Department closed the Powell renovation probe, removing the obstacle that had given Senator Thom Tillis leverage to slow Warsh.
▲ | Bloomberg reported on April 29 that Warsh cleared the Senate Banking Committee, putting him on track for a full-Senate vote before May 15.
▲ | The market still appears anchored to the earlier pro tem scenario even though the procedural facts have shifted.

Bayesian Calculation

Base rate: 28% YES from the current market, or 28c on the YES contract.

Positive update: The official term-end date, the dropped DOJ probe, and Warsh’s committee progress together move the handoff probability sharply higher because they remove the main path to delay.

Negative update: Powell has said he would serve pro tem if Warsh is not yet in place, so even a small Senate delay or contract-interpretation wrinkle can still preserve a NO tail.

Naly estimate: 84% YES, which maps to an 84c fair price on the same YES contract.

Alternative explanation: The market may be pricing contract wording rather than personnel odds. If traders think “out by May 15” requires a fully completed swearing-in, or if they think a pro tem bridge still counts as Powell remaining chair in practice, then a low YES price is less irrational than it looks.

What Would Make Us Wrong

A procedural slip is the main risk. If the full Senate vote slips, if a new ethics or legal complication reopens the path to delay, or if the market resolves around Powell still acting pro tem on May 15, then the NO side could still win despite the term-end date.

Fresh Checks

Federal Reserve press conference transcript, April 29, 2026

Reuters via Investing.com on Powell saying Warsh becomes chair when sworn

Reuters via Investing.com on DOJ dropping the Powell probe

Bloomberg on Warsh clearing the Senate Banking Committee

Event 2

US x Iran diplomatic meeting by May 31, 2026?

GeopoliticsContract · YESResolves May 31, 2026OpenMedium-High confidence

+70c

Max Payout if Correct

Polymarket Top Answer NO 70%

Naly Top Answer YES 68%
Trade on Polymarket →

Traders are overreacting to one rejection even though Pakistan-backed diplomacy is still active and another meeting is easier than a full peace deal.

Causal Chain

Cause Cause: The diplomatic channel is still alive: Pakistan remains in constant contact, Tehran just sent a written response, and U.S. officials are still negotiating both directly and through mediators.

↓

Effect Effect: That keeps the next meeting threshold much easier to clear than a final peace settlement, because both sides still need a venue to test amendments, ceasefire enforcement, and Hormuz terms.

↓

Projection Projection: Even after Trump called the latest Iranian response unacceptable, another qualifying diplomatic session before month-end remains more likely than the current market price suggests.

Key Factors

| Factor
▲ | AP reported on May 10 that Iran sent its response to the latest U.S. proposal via Pakistani mediators, which is evidence of an active process rather than a frozen channel.
▲ | Axios reported on May 6 that U.S. and Iranian officials were negotiating a one-page memo both directly and through mediators, with Islamabad or Geneva discussed as venues for the next phase.
▲ | AP reported on May 7 that Pakistan said it expected an agreement sooner rather than later and was in continuous contact with both capitals day and night.
▲ | Reuters reported on April 14 that talks could resume quickly in Pakistan despite the blockade pressure, reinforcing that mediator logistics are already built.
▼ | The market appears to be pricing the latest rhetorical setback as if it kills the meeting path, but high-friction negotiations usually create more sessions before they create a deal.

Bayesian Calculation

Base rate: 30% YES from the current market, or 30c on the YES contract.

Positive update: Existing mediator traffic, live draft-exchange behavior, and venue planning push the odds higher because they show process continuation, not merely abstract willingness.

Negative update: Trump’s public rejection raises the probability of delay, a pause in visible diplomacy, or a shift back to purely back-channel communication that may not satisfy the contract.

Naly estimate: 68% YES, which maps to a 68c fair price on the same YES contract.

Alternative explanation: The market may simply be betting that headline politics overwhelm process politics. If Trump’s “unacceptable” post hardens both sides’ public positions, traders could be correct that formal talks drift past May 31 even while private mediation continues.

What Would Make Us Wrong

We are most exposed to a format problem, not a total-collapse problem. If diplomacy continues only through written exchanges, if a meeting is planned but slips into June, or if military escalation makes public travel too costly, then the NO side can win even with an active channel.

Fresh Checks

AP on Iran sending its latest response through Pakistani mediators

AP on Pakistan saying it expects a deal sooner rather than later

Axios on the one-page U.S.-Iran memo and direct-plus-mediated talks

Reuters via Investing.com on talks potentially resuming despite the blockade

Event 3

MicroStrategy sells any Bitcoin by June 30, 2026?

MarketsContract · YESResolves June 30, 2026OpenMedium confidence

+33c

Max Payout if Correct

Polymarket Top Answer YES 67%

Naly Top Answer NO 58%
Trade on Polymarket →

The market is treating management’s new willingness to sell as if an actual sale is now more likely than not, despite ample financing alternatives.

Causal Chain

Cause Cause: Michael Saylor’s earnings-call comment broke the old “never sell” taboo, so traders instantly updated from “impossible” to “probable.”

↓

Effect Effect: That rhetorical break inflated the YES price faster than the underlying funding necessity changed, because possibility is being mistaken for near-term compulsion.

↓

Projection Projection: Strategy still has enough financing flexibility and enough treasury-brand incentive to avoid an actual Bitcoin sale before June 30 more often than not.

Key Factors

| Factor
▲ | Strategy’s May 5 results explicitly list debt and equity financing availability as a major variable, which matters because those channels still exist without requiring a BTC sale.
▲ | Strategy’s investor-relations page shows the Q1 2026 webinar and presentation were published on May 5, anchoring the sell discussion to a single fresh disclosure rather than a longer trend of actual disposals.
▲ | Strategy’s April 13 8-K announced another BTC acquisition, which reinforces that the operating default has still been accumulation, not liquidation.
▲ | Reuters-republished coverage on April 20 showed the company sold $2.54 billion in securities and used the proceeds to buy more bitcoin, a direct example of financing obligations without shrinking the treasury.
▲ | The strongest bull case for YES is Saylor’s own remark that the company would probably sell some bitcoin to fund a dividend, but even that sounds like a tactical inoculation move rather than a forced balance-sheet event.

Bayesian Calculation

Base rate: 67% YES from the current market, or 67c on the YES contract.

Positive update: Management has now publicly legitimized at least a small sale, so the probability of a symbolic or tactical disposal is materially above zero.

Negative update: Fresh securities issuance, the bitcoin-per-share framing, and the company’s identity as a treasury vehicle all push against doing an actual sale unless it is clearly accretive or operationally necessary.

Naly estimate: 42% YES, which maps to a 42c fair price on the same YES contract and leaves NO as our higher-probability answer.

Alternative explanation: The market may be right that symbolism matters more than economics here. Once management decides it wants to prove the market can absorb a small BTC sale, a tiny voluntary transaction would be enough to settle YES and would not require genuine financial stress.

What Would Make Us Wrong

A single token sale is the main risk. If Strategy chooses to sell even a trivial amount of bitcoin to establish precedent, satisfy dividend optics, or create future flexibility, the YES contract resolves regardless of whether the broader treasury strategy remains intact.

Fresh Checks

Strategy first-quarter 2026 financial results

Strategy investor-relations events and presentations page

Strategy’s April 13, 2026 BTC acquisition 8-K

Motley Fool transcript capturing the Q1 2026 earnings-call sell remark

Conclusion

The next catalysts are unusually concrete: a Warsh floor vote or swearing-in before May 15, any publicly acknowledged U.S.-Iran session in Islamabad or another mediator venue before May 31, and any Strategy 8-K or dividend-related disclosure before June 30 that turns a rhetorical sale option into an actual transaction. Those are the watchpoints that can flip this board fastest from May 11, 2026.

FAQ

Why does the lead paragraph name concrete prices?

Because a citation-ready answer should tell the reader exactly where the market and Naly disagree, not force them to infer the gap.

Why can Naly disagree even when the market has more information?

Because prediction markets often price salience and narrative speed faster than they price procedural mechanics, financing alternatives, or the difference between a live channel and a completed outcome.

Why link methodology and track record inside a roundup article?

Because trust in a mispricing call depends on calibration, resolution discipline, and showing our work publicly at /track-record, not just on making a bold claim.

Methodology

We start from market-implied priors, update with fresh public evidence, and ask whether the market is mispricing the causal chain or just reacting to the loudest headline. We publish calibration and resolution history on /track-record, deeper model context on /predictions/scorecard, and the broader framework on /methodology.

Disclaimer

This is probabilistic research for informational purposes, not financial advice.