Strategy (MSTR) Stock: Saylor Signals Bitcoin Buy as Exec Stock Sales Raise Eyebrows

TLDR

• Michael Saylor posted Strategy’s signature BTC acquisition chart on Sunday, widely read as a signal of a new Bitcoin purchase
• CEO Phong Le backed the message, saying Strategy’s goal is to “increase net Bitcoin and Bitcoin per share over time”
• Strategy sold 32 BTC in late May — its first sale since 2022 — sparking concern about dividend and liquidity pressures
• Bitcoin fell below $60,000 on Friday, its lowest level since October 2024, before recovering slightly to around $62,153–$63,104
• SEC filings show CEO Phong Le and CFO Andrew Kang plan to sell a combined $15 million in MSTR stock

Michael Saylor is doing what he does best: keeping the market guessing.

Strategy Inc, MSTR

On Sunday, Strategy’s executive chairman posted the company’s familiar Bitcoin purchase tracker chart on X, writing “A good time to add more dots.” Traders and analysts have come to see these posts as a reliable signal that a new BTC acquisition is on the way.

Strategy currently holds 843,706 Bitcoin, acquired at an average cost of $75,701 per coin. With Bitcoin trading around $62,153 at time of publication — down roughly 16.6% in the past seven days — any new purchase would likely come in below that average cost basis.

That rough week started when Strategy disclosed it had sold 32 Bitcoin — worth about $2.5 million — in late May. It was the company’s first BTC sale since 2022. While small relative to its 843,000+ coin treasury, the move rattled investors who have long viewed Strategy as a consistent, one-way buyer of Bitcoin.

The sale raised questions about whether the company might be forced to offload more Bitcoin to meet its dividend obligations or manage liquidity if prices keep falling.

Exec Stock Sales Add to the Pressure

Those concerns got louder on Friday when SEC filings revealed that two senior executives plan to sell a combined $15 million worth of MSTR stock. CEO Phong Le filed to sell roughly $11.1 million, and CFO Andrew Kang filed to sell about $3.9 million. Both transactions are tied to recently vested stock awards.

The timing — coming just as Bitcoin dipped below $60,000 for the first time since October 2024 — drew attention, even if the sales themselves are routine for vesting schedules.

Also last week, Strategy announced it had repurchased some of its corporate debt, which temporarily paused Bitcoin accumulation. That news briefly spooked traders who worried the company might need to sell BTC to fund the buybacks.

Preferred Dividend Vote Underway

Separately, Strategy shareholders are voting on whether to change the dividend payment schedule for its STRC preferred stock from monthly to twice monthly. The company says the switch would reduce reinvestment lag and increase price stability.

For the measure to pass, 50% of all 85 million STRC shares outstanding as of April 17, 2026 must vote in favor. The final tally is expected at Monday’s shareholder meeting.

Retail investors have historically voted only about 29% of their held shares in proxy seasons, compared to 77% for institutional holders, according to Harvard Law School Corporate Governance research from November.

Any new Bitcoin purchase announcement is expected to come Monday.

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