Strategy Repurchases 411 BTC for $30.2M Amid Sales Speculation

Highlights:

• Strategy has repurchased 411.5 BTC worth approximately $30.2 million. 
• The repurchase occurred a few hours after Strategy had deposited the same amount of BTC into Coinbase Prime. 
• Bitcoin has continued to trade above $70,000 after recording a slight decline in the past 24 hours. 

Michael Saylor’s Strategy has withdrawn 411.5 Bitcoin (BTC) worth roughly $30.2 million from Coinbase Prime. Lookonchain, a renowned crypto transaction tracker, reported the move in an X post on May 30. According to the tweet, the withdrawal occurred in two separate trenches. The first purchase involved 206.003 BTC valued at approximately $15.12 million, while the second involved 205.274 BTC worth $15.06 million. 

On May 29, Strategy deposited exactly 411.48 BTC valued at approximately $30.3 million into Coinbase Prime. The transfer raised suspicions about potential BTC selloffs. On the popular betting platform Polymarket, the odds that the company will sell its Bitcoin holdings on or before December 31, 2026, rose to about 84%.

Did Michael Saylor's @Strategy cancel its $BTC sale?

Strategy withdrew 411.5 $BTC($30.2M) back from #CoinbasePrime 5 hours ago.https://t.co/h1ETICLO7K pic.twitter.com/Ap5dyY2zPd

— Lookonchain (@lookonchain) May 30, 2026

Bitcoin Sales Speculations Remain High

While Strategy’s withdrawal move might have allayed market observers’ fears, the company’s financial position and BTC’s persistent price dips have continued to generate significant concerns. Since April, Strategy has been announcing weekly Bitcoin purchases. However, during the week ending May 25, the company announced that it repurchased $1.5 billion worth of convertible notes due 2029. 

The repurchase was at roughly an 8% discount to face value, which generated an incremental 0.7% BTC yield and reduced the company’s total debt to $6.7 billion. Strategy also announced that its 2026 year-to-date Bitcoin yield rose to about 13.3%. Meanwhile, the company still holds 843,738 BTC worth roughly $63.87 billion at an average cost of $75,700 per BTC.

Strategy Retires $1.5 Billion of Debt at Discount, Skips Bitcoin Buy

Strategy, the world's largest corporate Bitcoin holder, said it completed the repurchase of $1.5 billion of convertible notes due 2029 at an roughly 8% discount to face value, adding 0.7 percentage points to… pic.twitter.com/mP63NPSGgQ

— Wu Blockchain (@WuBlockchain) May 26, 2026

Arca CIO Slams Saylor’s Decision to Repurchase Bonds Due in 2029

In a May 28 X post, Arca CIO Jeff Dorman criticized Michael Saylor’s recent investment moves, including the company’s decision to repurchase $1.5 billion worth of convertible notes. The Arca CIO argued that adopting a conservative approach to BTC investments would have left Strategy in a stable financial position. 

However, the company chose to adopt a robust approach, with massive investments in preferred stock offerings that raised billions of dollars for the company while Bitcoin traded at high levels. Meanwhile, Bitcoin’s persistent declines have placed the company in a difficult financial position. Notably, Strategy’s preferred obligations climbed to about $15 billion. At the same time, the company’s annual dividend cost rose to approximately $1.5 billion. 

These figures have raised concerns about how the company could keep up with debt payments. To reassure investors, Strategy raised $2 billion through stock sales. This fund was meant to cover dividend payments for roughly 2 years. However, the company decided to use part of the fundraiser to buy back bonds due in 2029. This particular decision came as a huge surprise because the bonds reportedly carried a 0% interest rate. 

The Arca CIO queried:

“This is a baffling decision for a company with cash flow problems.  Why pay off 0% coupon debt with the only cash you have?” 

Bitcoin’s Price Dips Slightly as Strategy Repurchases 411.5 BTC

At the time of press, Bitcoin’s price is approximately $73,500 following a 0.2% decline in the past 24 hours. The asset has a market cap of approximately $1.47 trillion and a trading volume of about $33.5 billion. BTC’s Week-to-date, month-to-date, and year-to-date price change metrics showed declines of about 2.5%, 2.6%, and 30.7%, respectively.