Crypto

Michael Saylor moves $30 million in Bitcoin


Strategy and its executive chairman, Michael Saylor’s “never sell” stance, had become almost gospel in the Bitcoin (BTC) community.

But on May 5, he dropped a bombshell that the company is considering selling Bitcoin.

Now, a few weeks later, the company made a major Bitcoin move, hinting that the sale might be happening soon.

Related: Michael Saylor finally wants to sell Bitcoin

The push and pull of Bitcoin sale

Strategy’s every new Bitcoin purchase was treated as a bullish signal by the market. The “never sell” stance was almost a founding principle of the company’s newfound identity in 2020 when it changed its name from “MicroStrategy” to simply “Strategy.”

The first crack came during Strategy’s Q1 2026 earnings call, when Saylor suggested selling Bitcoin to pay dividends.

“We will probably sell some bitcoin to pay a dividend just to inoculate the market and send the message that we did it,” he said.

He quickly walked it back during an interview with Fortune, claiming his remarks were intended to “jam short-sellers and haters” rather than signal a genuine change of direction.

But the reversal didn’t stick for long. Most recently, during an interview with popular crypto influencer Natalie Brunell, Saylor said it was “not unlikely” that Strategy would sell some Bitcoin before the end of 2026.

Then came the purchase of bonds. Strategy revealed in a filing that it bought back $1.5 billion in face value of its 0% Convertible Senior Notes due 2029. Although there was some Bitcoin purchase as well in the same window, there was an entire week when the company did not purchase a single Bitcoin, hinting at the slowdown of the company’s aggressive Bitcoin shopping.

More from TheStreet Roundtable

Strategy moves Bitcoin to Coinbase Prime

On-chain analytics platform Lookonchain reported that Strategy deposited 411.48 Bitcoin worth about $30.3 million to an external wallet on May 28, which on-chain analytics platform Lookonchain identified as a Coinbase Prime address.

As per Arkham, the move happened in phases in the night hours of May 28.

Strategy moves Bitcoin worth $30.3 million (Source: Arkham)

Coinbase Prime is known as a platform used by institutional investors for custody and structured sales. So when assets move to the platform, the market always focuses on whether it is a change in custody structure or preparation for an actual disposal.

Large institutional holders move assets between custody accounts for portfolio rebalancing, pledging as collateral for credit facilities, facilitating OTC transactions, or simply reorganizing internal wallet infrastructure

In other words, while moving Bitcoin there doesn’t necessarily mean the company is selling, it puts the Bitcoin in a place where selling becomes very easy.

The move spurred betting on Polymarket over whether Strategy will sell Bitcoin before the end of 2026, with odds rising to 91%.

At press time, Strategy was largely flat but in the red and trading at $151.56 during the market hours.

Related: Why Saylor skipped Bitcoin buy this week

This story was originally published by TheStreet on May 29, 2026, where it first appeared in the MARKETS section. Add TheStreet as a Preferred Source by clicking here.



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