Michael Saylor Just Made His Biggest Bitcoin Bet of H2 2025

[Ben Graham]

Strategy reported its largest Bitcoin purchase in more than three months on Monday, only days after spending close to $1Bn on the cryptocurrency.

The firm, based in Tysons Corner, Virginia, said it bought 10,624 BTC for $963M. Most of the funding came from issuing new common stock. The latest purchase lifts Strategy’s total holdings to about 660,600 BTC. At current prices, that stack is worth roughly $60Bn.

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Why Does This Latest Bitcoin Purchase Stand Out for Strategy?

The size of this buy is notable. It equals all the Bitcoin the company acquired since mid-September, when the token traded near $115,000.

According to Yahoo Finance, Strategy’s shares traded around $180 on Monday and barely moved. The stock is still down by half over the past six months, but it has picked up +7.5% over the past week as Bitcoin stayed near the $90,000 mark.

Cantor Fitzgerald analysts said in a recent report that some investors have worried about a possible shift in Strategy’s approach to buying Bitcoin. They noted that talk about the company skipping the latest pullback had added to that concern. But the analysts said those fears were unnecessary.

Even with that view, Cantor joined other firms in cutting their price targets last week. They pointed to the risk that Strategy could be left out of MSCI indices. 

Reuters reported that the company has been in talks with MSCI ahead of the final call.

TD Cowen analysts shared the broader market’s worries about the MSCI outcome. But they also highlighted Strategy’s decision to set aside a $1.4Bn cash reserve. 

They described it as a careful move that gives the firm enough room to keep paying dividends.

Strategy last bought a similar amount of Bitcoin shortly after it closed STRC, a $2.5Bn preferred share offering announced earlier this year. 

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How Does Strategy’s New Stock Sale Compare to Its Earlier Funding Round?

That raise was the largest crypto-linked equity deal at the time. Monday’s update, by comparison, was more standard. 

The company issued more common stock and also sold $44M in STRD, a preferred class that pays a 10% annual, non-cumulative cash dividend.

Strategy’s recent activity also stands apart from other firms trying to follow its Bitcoin-accumulation model. 

Metaplanet, Japan’s largest corporate holder of Bitcoin, is preparing its own preferred share sale but has not reported a new purchase since October.

Twenty One Capital, a Bitcoin-focused firm backed by Tether and SoftBank, is set to list on the New York Stock Exchange this week under the ticker XXI.

Co-founder and CEO Jack Mallers said on X that the company has started moving its Bitcoin ahead of the debut. He confirmed that 43,500 BTC were released from escrow. 

Twenty One expects to begin trading on the @NYSE under the ticker $XXI on December 9th.

As part of the closing process, we’ll be moving our over 43,500 bitcoin out of escrow and into our custody. We’ll update our proof of reserves accordingly.

Transparency is the standard. pic.twitter.com/kEyT5qWYY6

— Jack Mallers (@jackmallers) December 7, 2025

Based on Monday’s prices, that stack was worth about $3.9Bn.

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