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Michael Saylor Signals Another $BTC Buy for Strategy, $13 Billion Underwater

Michael Saylor signaled Monday that Strategy plans to purchase bitcoin again — a move that would mark the firm's fourth consecutive week of $BTC buying — while the company's position sits roughly $13 billion in the red.…

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Mohamed Naseem
Malé · 3 min read
28 June 2026Markets desk
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Michael Saylor signaled Monday that Strategy plans to purchase bitcoin again — a move that would mark the firm's fourth consecutive week of $BTC buying — while the company's position sits roughly $13 billion in the red. The anticipated transaction would be confirmed in a Monday regulatory filing.

A Streak Held Through a Shrinking Tranche

Strategy's most recent disclosed purchase was 520 bitcoin, transacted on June 22 and flagged as the company's smallest recent tranche. The reduction in lot size was notable; the continuity of the buying streak was not broken. If Saylor's Monday signal produces a filing, it extends four uninterrupted weeks of accumulation.

The tranche shrinkage is the variable that merits scrutiny. A buyer who has been accumulating at scale and then reduces its lot size — while keeping the weekly cadence intact — is telling the market something, though the source does not specify what. Constraint and strategy look identical from the outside until they do not.

What $13 Billion Underwater Means

"Underwater" is balance-sheet language for a losing position: Strategy's average cost to acquire its $BTC holdings exceeds what the market currently prices bitcoin at. The gap, per the source, is approximately $13 billion. For a publicly traded company, that figure shows up in regulatory disclosures — the same Monday filings Saylor has been using to announce each week's buy.

The buy-despite-losses posture has been consistent. The June 22 purchase was small by recent standards, but it still happened. Monday's signal suggests the pattern is not changing.

Who Is on the Other Side

Strategy is a one-way buyer of $BTC. Four straight weeks of purchasing means four straight weeks of counterparties who took the other side and sold. The source does not identify them. But the structure of the trade is worth stating plainly: a company sitting $13 billion underwater is signaling it will buy more. Someone is selling to them. Knowing who, and at what cost basis, is the question the headline does not answer.

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Tickers$BTC
Categorycrypto

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Key takeaways

Frequently asked

What does it mean that Strategy is $13 billion underwater?

It means Strategy's average cost to acquire its bitcoin holdings exceeds bitcoin's current market price, leaving the position about $13 billion in the red.

How many weeks in a row has Strategy been buying bitcoin?

If Saylor's Monday signal produces a filing, it would extend the firm's accumulation to four uninterrupted weeks.

How large was Strategy's most recent bitcoin purchase?

Strategy's most recent disclosed purchase was 520 bitcoin on June 22, described as its smallest recent tranche.

Who is selling the bitcoin to Strategy?

The article does not identify the counterparties; it only notes that four straight weeks of buying means four straight weeks of sellers taking the other side.

How does Strategy announce its bitcoin purchases?

Strategy confirms each week's buy through Monday regulatory filings, where its underwater position also appears in disclosures.