Daily Market Mispricings: 2 Finance Events Where We Disagree With Polymarket — May 19, 2026

TL;DRNaly’s clearest disagreements on May 19, 2026 are both Strategy/MicroStrategy sale markets: Polymarket prices a June 30 bitcoin sale at 66c YES and a December 31 sale at 85c YES, but we mark those nearer 22c and 35c. The sharpest reason is structural: every fresh filing still shows the company raising outside capital and adding BTC, while a multibillion-dollar cash reserve lowers near-term pressure to liquidate.

Key Takeaways

Polymarket appears to be pricing management’s new willingness to mention bitcoin sales as if it were proof of imminent execution.

Strategy’s freshest observable behavior still points the other way: new BTC purchases, active ATM fundraising, and a large stated cash reserve.

The June 30, 2026 contract looks like the cleaner answer flip because the company announced a major BTC purchase even after disclosing that a note repurchase could be funded with bitcoin-sale proceeds.

The December 31, 2026 contract deserves a higher sale probability than the June market, but not an 85% implied likelihood.

2 Mispricings at a Glance

Event Snapshot

MicroStrategy sells any Bitcoin by December 31, 2026?

Buy NO / fade YES Resolves July 1, 2026 Open 86 confidence

Polymarket Top Answer YES 85%

Naly Top Answer NO 65%

Max Payout if Correct +85c

0c 50c $1.00

Polymarket Naly

Why we disagree: The market is extrapolating optionality into necessity, but the latest filings still show capital raising and BTC accumulation, not liquidation.

Event Snapshot

MicroStrategy sells any Bitcoin by June 30, 2026?

Buy NO / fade YES Resolves July 1, 2026 Open 88 confidence

Polymarket Top Answer YES 66%

Naly Top Answer NO 78%

Max Payout if Correct +66c

0c 50c $1.00

Polymarket Naly

Why we disagree: The company explicitly kept bitcoin sales as one funding option, but then immediately kept buying BTC, which argues sale remains a backstop rather than the base case.

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

MicroStrategy sells any Bitcoin by December 31, 2026?

MarketsContract · Buy NO / fade YESResolves July 1, 2026Open86 confidence

+85c

Max Payout if Correct

Polymarket Top Answer YES 85%

Naly Top Answer NO 65%
Trade on Polymarket →

Polymarket’s quoted price here is YES 85c, meaning the current entry price for the YES side is about 85 cents and the market is implying roughly an 85% chance that Strategy sells any bitcoin before this contract resolves. Our estimate is YES 35%, which means a 35c fair price on the same YES side and flips our top answer to NO. If you buy NO at the market’s implied 15c, the max payout if correct is 85c; that is separate from the fair-value edge, which is the gap between our 65c NO estimate and the market’s 15c NO price.

Causal Chain

Cause Cause bullet: The market heard management open the door to possible bitcoin sales and repriced that statement as a near-inevitable treasury action.

↓

Effect Effect bullet: But the company’s observed behavior after that statement was still to raise outside capital and add to its BTC stack, which weakens the case that liquidation is the preferred path.

↓

Projection Projection bullet: Over the longer December window, a sale is possible if funding conditions worsen or management chooses a symbolic small sale, but that is still materially below an 85% base case.

Key Factors

| Factor
▲ | Strategy’s May 18, 2026 filing said it acquired 24,869 BTC and now holds 843,738 BTC, which is the opposite of a balance-sheet pivot toward disposal.
▲ | The May 14, 2026 8-K on repurchasing 2029 notes listed three funding sources: cash reserves, ATM security sales, and bitcoin-sale proceeds. That language creates optionality, not proof of execution.
▲ | Strategy’s May 5, 2026 first-quarter results said it had $2.21 billion in cash and cash equivalents as of March 31, 2026.
▲ | The 2025 annual report says bitcoin is the primary treasury reserve asset and that the company expects to continue accumulating bitcoin, while also evaluating liquidity needs and capital structure continuously.
▲ | The same annual report says forced selling becomes more plausible if notes mature or are redeemed without conversion, but that is a contingency path, not current evidence of an active sell program.

Bayesian Calculation

Base rate: Start from the market’s 85% YES because management rhetoric and debt complexity do matter.

Positive update: Management has now explicitly normalized the possibility of selling bitcoin, and the note repurchase filing keeps BTC-sale proceeds on the menu.

Negative update: Fresh filings still show a large cash buffer, active ATM capacity, and net BTC accumulation immediately after the sale scare.

Naly estimate: 35% YES, or a 35c fair price on YES and 65c fair price on NO.

Alternative explanation: The bullish YES case is that management may choose a deliberately tiny symbolic sale before year-end to prove flexibility, even if liquidity is not strained. That path does not require distress, just a desire to reset market expectations.

What Would Make Us Wrong

We are wrong if Strategy quickly follows the note repurchase with a bitcoin sale announcement, if ATM funding weakens sharply, or if dividend and debt-service optics push management toward demonstrating treasury liquidity earlier than we expect.

Fresh Checks

Strategy Acquires 24,869 BTC and Now Holds 843,738 BTC

Strategy Announces First Quarter 2026 Financial Results

Strategy 8-K on Repurchases of 2029 Notes

Strategy 2025 Annual Report

Event 2

MicroStrategy sells any Bitcoin by June 30, 2026?

MarketsContract · Buy NO / fade YESResolves July 1, 2026Open88 confidence

+66c

Max Payout if Correct

Polymarket Top Answer YES 66%

Naly Top Answer NO 78%
Trade on Polymarket →

Polymarket’s quoted price here is YES 66c, so the market is assigning about a 66% probability to a bitcoin sale before June 30, 2026. Our estimate is YES 22%, which means a 22c fair price on that same YES side and flips our top answer to NO. Buying NO at the market’s implied 34c would offer a max payout if correct of 66c, while the fair-value edge is the difference between our 78c NO estimate and that 34c market price.

Causal Chain

Cause Cause bullet: Traders appear to be treating the May 14 note-repurchase filing as a near-term trigger for BTC liquidation.

↓

Effect Effect bullet: Yet by May 18 the company had announced another large BTC purchase, signaling that outside financing and reserves still sit ahead of selling coins in the capital stack.

↓

Projection Projection bullet: Unless financing windows slam shut in the next six weeks, the more likely path into late June is continued flexibility without an actual sale.

Key Factors

| Factor
▲ | The note repurchase is expected to settle on or about May 19, 2026, so the highest-pressure near-term funding event is happening now, not abstractly months from now.
▲ | Even with that event pending, Strategy disclosed a fresh BTC purchase on May 18, 2026 rather than reporting a sale.
▲ | Q1 results reported $2.21 billion in cash and cash equivalents as of March 31, 2026, which matters because this market is about the next few weeks, not the full year.
▲ | Strategy’s purchases page showed 843,738 BTC as of the latest update, reinforcing that the immediate operating pattern remains accumulation.
▲ | Management’s willingness to mention bitcoin sales is new information, but willingness is not the same thing as urgency.

Bayesian Calculation

Base rate: Begin from 66% YES because the company itself has now acknowledged bitcoin-sale proceeds as a possible funding source.

Positive update: There is a real catalyst window around the note repurchase, and a small sale would satisfy contract resolution.

Negative update: The company kept raising capital, kept buying BTC, and still has disclosed cash resources, all of which cut against an immediate need to sell.

Naly estimate: 22% YES, or a 22c fair price on YES and 78c fair price on NO.

Alternative explanation: The market may be assuming not a large liquidation but a token sale. If management wants to show the treasury is truly fungible, even a small one-off transaction would cash the YES side.

What Would Make Us Wrong

We are wrong if the May note repurchase is funded partly with BTC-sale proceeds, if management decides to stage a symbolic sale to de-risk future communication, or if bitcoin volatility suddenly shuts the ATM window and makes a sale the fastest clean funding tool.

Fresh Checks

Strategy 8-K on Repurchases of 2029 Notes

Strategy Acquires 24,869 BTC and Now Holds 843,738 BTC

Strategy Announces First Quarter 2026 Financial Results

Strategy Bitcoin Purchases Dashboard

Conclusion

The watchpoints into the next few weeks are concrete: whether the May 19, 2026 note repurchase is funded with cash, ATM issuance, or disclosed BTC-sale proceeds; whether Strategy keeps posting new purchase updates; and whether management turns a theoretical sale option into an actual treasury action. Until one of those catalysts flips from possibility to fact, we think Polymarket is overpricing near-term bitcoin sales.

Methodology

Naly treats each quoted cents price as an implied probability for a $1 binary contract, then rebuilds fair value from fresh evidence, incentives, and path dependence rather than from headline sentiment alone. We compare the market-implied path with our own causal base case, publish the disagreement, and keep a public record at our track record.

Disclaimer

This article is for informational purposes only and reflects Naly’s probability estimates as of May 19, 2026. It is not investment advice, not a solicitation to trade, and not a guarantee of outcome; prediction markets can remain mispriced longer than a thesis stays comfortable.