Saylor’s Bitcoin Flip-Flop: Will He Sell or Won’t He?

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In a universe where the only certainty is uncertainty, Michael Saylor has decided to add a dash of cosmic confusion to the mix. During a Coin Stories podcast interview, he declared that a Strategy Bitcoin sale before the year’s end is “not unlikely.” Yes, you heard that right. The man who once vowed to hold Bitcoin until the heat death of the universe is now entertaining the idea of letting a few slip through his fingers. What’s next? Will the Hitchhiker’s Guide to the Galaxy start recommending Vogon poetry as light reading?

  • Saylor, in a moment of what can only be described as intergalactic indecision, told Natalie Brunell it was “not unlikely” Strategy would part with some Bitcoin before the year’s end. Apparently, his “never-sell” stance was just a suggestion, like the speed limit on the hyperspace bypass.
  • He also claimed that any model relying solely on equity, credit, or Bitcoin sales underperforms. Because, of course, the universe works best when you throw a bit of everything into the blender and hope for the best.
  • Strategy currently hoards 818,334 BTC, valued at a cool $65 billion, and aims to maximize Bitcoin per share over a seven-year horizon to 2033. Because why stop at the moon when you can aim for the entire galaxy?

Strategy’s executive chairman, Michael Saylor, dropped this bombshell on the Coin Stories podcast, casually mentioning it’s “not unlikely” the company will sell some Bitcoin before the year’s end. This is the financial equivalent of saying, “I’m not unlikely to eat the last slice of pizza,” while eyeing the fridge.

“I think it’s not unlikely that we’ll sell some Bitcoin between now and the end of the year,” Saylor mused. “Any model that we put together that’s limited only to equity or only to credit or only to Bitcoin always underperforms.” Translation: Life’s too short to stick to one plan when you can have a buffet of options.

Why Saylor’s Bitcoin Sale in 2026 Might Just Be a Cosmic Prank

These comments come hot on the heels of Strategy’s Q1 earnings call, where Saylor floated the idea of selling Bitcoin to fund dividends, claiming it would “inoculate the market.” Because nothing says stability like injecting a bit of chaos into the system. Crypto.news has, of course, been all over this, including the $12.54 billion Q1 net loss that preceded it. After all, what’s a few billion when you’re playing the long game?

Saylor described Strategy’s capital management as “programmatic and data-driven,” with liabilities balanced against a mix of cash, equity, credit, and Bitcoin. The company holds 818,334 BTC, acquired for approximately $61.6 billion at an average price of $75,527. Because why buy one Bitcoin when you can buy enough to fill a spaceship?

He also assured everyone that Strategy has no plans to retire its STRF, STRD, and STRK preferred products, calling them “useful parts of the capital structure.” Meanwhile, convertible bonds remain senior liabilities to be retired over time. Because even in the world of finance, some things are just too stubborn to let go.

What a Strategy Bitcoin Sale Would Mean for the Markets (or Not)

Saylor was quick to point out that any sale would be a drop in the ocean compared to Bitcoin’s daily market liquidity, estimated at $20 to $50 billion. He even argued that Strategy could buy roughly 20 Bitcoin for every one sold if dividends were fully funded through BTC sales. Because why sell when you can just… sell and buy more? It’s like a financial Möbius strip.

Crypto.news has previously noted Saylor’s framing of Strategy’s three-layer capital structure: Bitcoin as digital capital, STRC as digital credit, and MSTR as leveraged equity. The firm’s seven-year goal is to maximize Bitcoin per share by 2033. Because if you’re going to dream, dream big-like, interstellar big.

Saylor insists that this long-term view makes 2026 Bitcoin sales a capital allocation decision, not a reversal of conviction. So, it’s not that he’s changed his mind; he’s just… recalibrating his reality. Sounds about right for the man who once said, “The best way to predict the future is to invent it.” Or was that someone else? Who can keep track?

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2026-05-23 13:28