Morning Minute: Saylor Sells Bitcoin for First Time Since 2022

Morning Minute is a daily newsletter written by Tyler Warner. The analysis and opinions expressed are his own and do not necessarily reflect those of Decrypt. And check out our new daily news show covering all of the top stories in 5 minutes, downloadable on Apple Pod or Spotify.

📉 Saylor Sells Bitcoin for First Time Since 2022

Strategy disclosed that it sold 32 BTC between May 26 and May 31 at an average price of $77,135, raising about $2.5 million. Well, it's the company's first Bitcoin sale since December 2022. And it comes after years of Saylor bullposting things like "Never sell your Bitcoin" or "Sell your kidney, but not your Bitcoin." The proceeds will go directly toward funding distributions on STRC preferred stock, which Saylor now finds himself owing a boatload of thanks to STRC's popularity. "Our goal is to make $STRC the best credit instrument in the world." pic.twitter.com/gMhUlT3jXu — Michael Saylor (@saylor) June 1, 2026

The market did NOT like the news. Strategy fell by 6% on Monday while Bitcoin has fallen below $70k and back to a near two-month low of $69,500. The number itself is almost comically small. The 32 coins sold represent about 0.0038% of Strategy's total position. In the same week, the company raised $128.3 million selling its own common shares through its at-the-market program, dwarfing the Bitcoin sale by a factor of fifty.

But that's not the problem. Strategy carries approximately $13.5 billion in total preferred equity obligations with an annual dividend burden of roughly $1.2-1.4 billion, against a cash reserve of just $871 million. That means without any new STRC issuance, the company has less than nine months of dividend coverage on hand.

So the market's current problem is—how much more will Saylor sell going forward? He just changed from being a passive Bitcoin investor who only buys, to an active fund manager that buys and sells. And that change will take some time for the market to absorb. Now if there are no more sells for awhile or they remain small in nature, this could blow over. But if they escalate in size and or frequency, that likely spells near-term pain.

🤯 Polymarket Says Saylor Didn't Sell Bitcoin in May

The Strategy Bitcoin sale has created one of the most unusual Polymarket disputes in the platform's history—and it's likely going to cause the team some serious headaches and potentially cause an overhaul to its resolution system. A contract asking "Will Strategy sell Bitcoin in May 2026?" had accumulated over $50 million in bets—and is now heading toward a NO resolution, despite the fact that Strategy sold Bitcoin in May.

Here's the situation: Strategy's 8-K disclosed that it sold 32 Bitcoin between May 26 and May 31. The transactions happened in May. But the 8-K was filed on June 1. The contract's resolution criteria specified: "The primary resolution source for this market will be information from MSTR and on-chain data, however a consensus of credible reporting will also be used."

Now the NO side is arguing that the reporting came after the May 31 deadline and thus should not count. The YES side argues the transactions are onchain and the 411 BTC Coinbase Prime transfer visible to Arkham on May 26 constitutes disclosure. At time of writing, it appears that NO bettors are winning and have UMA on their side. Which is absolutely the wrong outcome for the "spirit" of this bet. Polymarket was supposed to be a "truth machine." Now it's resolving $50M markets based on technicalities. Users aren't going to like this one…

The Morning Minute spans crypto and NFT news and market analysis, written by Tyler Warner, an ex-banking consultant turned high-volume NFT trader, Pudgy Penguin maxi, and NFT market analyst at Lucky Trader. Morning Minute is a daily newsletter written by Tyler Warner. The analysis and opinions expressed are his own and do not necessarily reflect those of Decrypt. And check out our new daily news show covering all of the top stories in 5 minutes, downloadable on Apple Pod or Spotify.