Will Strategy Sell Bitcoin? Saylor Says ‘Never Sell’ Needed a Reset

Michael Saylor has said Strategy may sell Bitcoin when needed, marking a careful change from his long-running “never sell” message. 

The Strategy executive chairman said the company must show that Bitcoin remains a usable asset, not a locked reserve that cannot support the business.

During his appearance on Scott Melker’s The Wolf of All Streets podcast, Saylor said Strategy needed to avoid making “never sell” sound like Bitcoin could not be used as a working asset. He said Strategy holds about $65 billion worth of Bitcoin and needs to show it can use that liquidity if needed. He framed the message as a way to protect the asset that supports most of the company’s value.

Dividend costs keep pressure on Strategy

The debate follows Strategy’s first-quarter results, when the company reported a $12.54 billion net loss. Strategy said it held 818,334 BTC as of May 3, with an average purchase price of about $75,537 per coin. The company also reported $11.68 billion raised year to date.

Saylor has said any Bitcoin sale would not mean Strategy is stepping away from accumulation. As previously reported, he said, “Even if we were to sell one Bitcoin, we’d be buying 10 to 20 more Bitcoin.” That statement remains tied to Strategy’s view and depends on market prices, financing access, and investor demand.

In addition, Strategy added more attention to the issue after filing a plan to repurchase about $1.50 billion of its 2029 convertible notes. The filing said the estimated cash repurchase price is about $1.38 billion. It also said Strategy may fund the deal with cash reserves, ATM equity proceeds, or proceeds from Bitcoin sales.

The expected settlement date is around May 19, 2026, subject to normal closing conditions. After the deal closes, Strategy plans to cancel the repurchased notes. About $1.50 billion of the 2029 notes would remain outstanding after the cancellation.

Strategy keeps buying as sales debate grows

Despite the sales debate, Strategy has continued to add Bitcoin. The company bought 535 BTC for about $43 million between May 4 and May 10, at an average price of about $80,340 per BTC. That purchase lifted total holdings to 818,869 BTC as of May 10.

Separate updates also showed STRC trading activity reaching $1.53 billion in daily liquidity, adding more focus to Strategy’s use of preferred stock products to support Bitcoin purchases. The same update said no new Bitcoin purchase had been announced from that STRC activity at the time.