Michael Saylor buys back $1.5B worth debt

For four years, Michael Saylor's message to the crypto world was the same, buy Bitcoin (BTC), accumulate, but never sell. 

Strategy (NASDAQ: MSTR), the company he chairs, built one of the most aggressive corporate Bitcoin treasuries in history on that single creed. 

But in the past two weeks, Saylor did something different. He bought bonds, not Bitcoin.

Related: Analyst predicts 140% upside for MicroStrategy stock

A shift in Bitcoin 'Strategy'

Saylor had positioned Strategy as the world's foremost publicly traded Bitcoin maximalist, piling into BTC week after week throughout 2025 and into 2026, sometimes for billions at a time. 

The pattern was so reliable that it had its own signal. Saylor would often hint on Sundays with an "Orange Dot" post on X, pointing at the next Bitcoin purchase. 

However, the Q1 2026 earnings call on May 5 changed the tone. Saylor told investors that Strategy may "probably sell some bitcoin to pay a dividend just to inoculate the market." 

This broke a long-standing public pledge against ever selling Bitcoin.

On May 24, Saylor posted that Strategy had "bought bonds, not bitcoin" during the week. 

But this was not the first time the company had skipped buying Bitcoin this year. Strategy had paused in early May ahead of earnings, adhering to reporting rules.

More from TheStreet Roundtable

• Eric Trump has a stark message on selling Bitcoin
• Ondo Finance founder Nathan Allman passes away
• Fed reopens controversial payment proposal

Saylor skips Bitcoin for debt

On May 26, Strategy confirmed the details. 

Between May 11 and May 25, the company repurchased $1.5 billion in face value of its 0% Convertible Senior Notes due 2029. 

The cash outlay was roughly $1.38 billion, at an 8% discount to par. The transaction generated a 0.7% incremental BTC Yield, a BTC Gain of 4,391 coins, and a BTC dollar gain of $333 million. 

Strategy's aggregate convertible debt fell from $8.2 billion to $6.7 billion after the purchase. 

In the same window, between May 11 and 17, Strategy also bought 24,869 BTC for $2.01 billion, funded largely by STRC preferred-stock sales. Strategy now holds 843,738 BTC while the USD Reserve stands at $871 million.

At press time, MSTR stock was trading 1.37% at $162.08 during pre-market hours.

Related: JPMorgan predicts a $30B Bitcoin buy is happening this year