Strategy’s Bitcoin-buying model has come back under scrutiny after Grayscale warned that current share prices could limit its ability to continue accumulating. The concern emerged amid a Bitcoin sale, pressure from STRC dividends and doubts over whether Strategy can keep financing purchases without stronger investor demand.

According to the data, Strategy, led by Michael Saylor, has suffered total losses of more than $12.4 billion on its Bitcoin portfolio, while BitMine, led by Tom Lee, has lost more than $10 billion on its Ethereum portfolio.

The sUSDat stablecoin lost its dollar peg, falling by 7% to $0.93 on Wednesday, 3 June, according to blockchain analysts at PeckShield. On Thursday, the decline became even deeper: for a short time, the stablecoin dropped to $0.90.

Analysts at The Kobeissi Letter said that Strategy, formerly MicroStrategy, the largest corporate holder of Bitcoin, has faced what they estimate to be the largest unrealised loss in the history of its investments in the leading cryptocurrency.

Strategy's sale of 32 $BTC turned a relatively small transaction into a significant test for corporate Bitcoin treasuries. The question is no longer whether public companies hold $BTC. Investors are now watching how these companies meet their cash obligations while attempting to maintain their Bitcoin positions.

Cryptocurrency

According to the latest data, Strategy made its first Bitcoin sale, selling a total of 32 BTC at a price of $77,135 per coin.

Strategy chief Michael Saylor has indicated that the company is preparing to announce another Bitcoin purchase. Saylor posted a bubble chart from StrategyTracker.com on X, showing all of the company’s Bitcoin purchases over nearly the past six years. The accompanying post traditionally hinted at new purchases.

Strategy’s preferred shares (STRC) closed below the established $100 par value on May 28, 2026. In pre-market trading, they recovered part of the decline but still failed to move back above that level, according to Yahoo Finance.

The world's largest Bitcoin treasury and business intelligence firm, Strategy, has revealed its total Bitcoin purchase of 2026, scooping up all Bitcoin mined this year and more.

Strategy has repurchased $1.5 billion of its own convertible notes maturing in 2029. The transaction was carried out at a discount of around 8% to par.

Strategy’s perpetual preferred shares of the STRC series recorded a historic daily trading volume of $1.53 billion on May 15, becoming the company’s primary financing instrument for Bitcoin purchases in 2026.

Strategy, the largest institutional investor in Bitcoin ($BTC), announced a $1.5 billion bond repurchase. In an official statement, the company said it had entered into agreements with certain investors to repurchase approximately $1.5 billion worth of zero-interest convertible notes due in 2029.

Michael Saylor, one of the most influential figures in the cryptocurrency world, spoke at Consensus 2026 in Miami about major changes to Strategy’s Bitcoin strategy and his long-term vision for the future.

Other

Today’s sharp rise in Bitcoin prices has once again drawn attention to the balances of institutional investors, with particular focus on the current profit/loss status of Michael Saylor and his company Strategy regarding their Bitcoin positions.

Cryptocurrency

Strategy Inc. is accelerating its Bitcoin accumulation, surpassing the network’s issuance, highlighting supply compression dynamics as treasury performance metrics show rising Bitcoin yield, profit, and sustained large-scale buying pressure.

Strategy reported no purchases of Bitcoin over the past week, marking the first pause in its weekly accumulation since December 2025. The update, filed via Form 8-K, ends a 13-week streak of continuous buying that had become a closely watched indicator of corporate demand.