Points of Focus

• Novogratz said Saylor’s 32 BTC sale sent the wrong signal to investors.
• Strategy sold $2.5 million in Bitcoin before a $101 million buyback days later.
• The trade reignited debate over Strategy’s long-standing “never sell” stance.

Michael Saylor’s decision to sell 32 Bitcoin for the first time in more than three years is still drawing debate, even after Strategy returned to the market days later with a $101 million purchase. 

Mike Novogratz, chief executive of Galaxy Digital, believes the transaction carried far more weight as a signal than as a treasury move. He argued that the subsequent $101 million purchase may have helped restore confidence after investors interpreted the sale as a break from Strategy’s long-standing approach.

Novogratz discussed the sale during a recent appearance with Anthony Scaramucci, arguing that Saylor should have used equity financing instead of selling Bitcoin. “I think it was a terrible mistake,” Novogratz said, adding that he would have preferred Strategy to sell stock instead of Bitcoin.

Why did Michael Saylor sell 32 Bitcoin for $2.5M and then buy $101M worth days later?

Novogratz thinks it was a strategic signal – and a mistake.

"I think it was a terrible mistake… I'd rather have him sell Micro Strategy stock."

The theory: Saylor wanted to prove to… pic.twitter.com/2haAJgED54

— Milk Road (@milkroaddaily) June 15, 2026

Why Strategy sold 32 BTC

Strategy sold 32 BTC between May 26 and May 31 for roughly $2.5 million, according to a June 1 filing with the US Securities and Exchange Commission. The company said proceeds from the sale would help fund distributions tied to its preferred shares, while executives later described the transaction as part of normal treasury management.

Phong Le, Strategy’s chief executive, told CNBC that the sale also served as a way to test internal selling procedures and demonstrate to preferred shareholders that Bitcoin could be liquidated if necessary. The company generated a tax loss from the transaction while retaining more than 845,000 BTC on its balance sheet.

Michael Saylor addressed criticism during BTC Prague on June 11, telling attendees that his long-standing advice to “never sell your bitcoin” was aimed at individual investors and didn’t prevent a company from selling assets to meet financial obligations.

Here is the answer on stage of @BTCPrague why Michael @saylor sold 32 BTC pic.twitter.com/5vGM0P9Rwh

— Alex Bragin (@BraginRights) June 11, 2026

$101 million buyback revives debate

The controversy intensified because Strategy resumed buying Bitcoin shortly after the sale. The company acquired 1,550 BTC for approximately $101 million at an average price of $65,332 per coin, raising its holdings to 845,256 BTC.

Novogratz suggested the purchase was meant to reassure investors after Strategy’s 32 BTC sale. Bitwise CIO Matt Hougan similarly argued the sale was immaterial, but noted investors have come to expect Strategy to keep buying Bitcoin and rarely, if ever, sell. 

Others disagree that the transaction represented a mistake. Cole Walmsley, chief executive of Strive Asset Management, said companies should focus on maximizing returns for common shareholders and argued that showing a willingness to sell assets when appropriate can be part of prudent capital allocation.

The 32 BTC sale accounted for about 0.004% of Strategy’s Bitcoin holdings, yet it sparked a week-long debate over whether a company built around a “never sell” philosophy can dispose of even a small amount without weakening investor confidence in its long-term Bitcoin strategy.