Michael Saylor buys back $1.5B worth debt

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For 4 years, Michael Saylor's connection to the crypto satellite was the same, bargain Bitcoin (BTC), accumulate, but ne'er sell.

Strategy (NASDAQ: MSTR), the institution helium chairs, built 1 of the astir assertive firm Bitcoin treasuries successful past connected that azygous creed.

But successful the past 2 weeks, Saylor did thing different. He bought bonds, not Bitcoin.

Related: Analyst predicts 140% upside for MicroStrategy stock

A displacement successful Bitcoin 'Strategy'

Saylor had positioned Strategy arsenic the world's foremost publically traded Bitcoin maximalist, piling into BTC week aft week passim 2025 and into 2026, sometimes for billions astatine a time.

The signifier was truthful reliable that it had its ain signal. Saylor would often hint connected Sundays with an "Orange Dot" station connected X, pointing astatine the adjacent Bitcoin purchase.

However, the Q1 2026 net telephone connected May 5 changed the tone. Saylor told investors that Strategy whitethorn "probably merchantability immoderate bitcoin to wage a dividend conscionable to inoculate the market."

This broke a long-standing nationalist 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 archetypal clip the institution had skipped buying Bitcoin this year. Strategy had paused successful aboriginal May up of earnings, adhering to reporting rules.

Saylor skips Bitcoin for indebtedness

On May 26, Strategy confirmed the details.

Between May 11 and May 25, the institution repurchased $1.5 cardinal successful look worth of its 0% Convertible Senior Notes owed 2029.

The currency outlay was astir $1.38 billion, astatine 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 summation of $333 million.

Strategy's aggregate convertible indebtedness fell from $8.2 cardinal to $6.7 cardinal aft the purchase.

In the aforesaid window, betwixt May 11 and 17, Strategy besides bought 24,869 BTC for $2.01 billion, funded mostly by STRC preferred-stock sales. Strategy present holds 843,738 BTC portion the USD Reserve stands astatine $871 million.

At property time, MSTR banal was trading 1.37% astatine $162.08 during pre-market hours.

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

This communicative was primitively published by TheStreet connected May 26, 2026, wherever it archetypal appeared successful the MARKETS section. Add TheStreet arsenic a Preferred Source by clicking here.

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