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Breaking News: Bullish Shift For TON: Price Breaks Above $2 Following Telegram CEO’s Gram News

Strategy Sells Bitcoin For First Time Since 2022 Tax-Loss Trade

Jake Simmons
Jake Simmons
Last Updated: June 2, 2026 5:00 am
3 mins read
Strategy Sells Bitcoin For First Time Since 2022 Tax-Loss Trade

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Strategy sold a small portion of its Bitcoin holdings last week, marking the company’s first disclosed BTC sale since its December 2022 tax-loss harvesting transaction. The sale is notable less for its size than for what it signals: Strategy is now willing to use a sliver of its Bitcoin stack to service the preferred equity structure it has built around its balance sheet.

According to a Form 8-K filed with the US Securities and Exchange Commission, Strategy sold 32 BTC between May 26 and May 31 for roughly $2.5 million. The average sale price was $77,135 per bitcoin, net of fees and expenses. The company said proceeds from the sale are expected to be used to fund distributions on preferred stock.

Why Did Strategy Sell Bitcoin?

The transaction is the first Bitcoin sale disclosed by Strategy since December 2022, when the company sold 704 BTC for tax-loss harvesting purposes before buying back more bitcoin two days later. That earlier sale was widely framed as a tax maneuver rather than a strategic reduction in exposure. The new sale is different in character: it appears tied to preferred stock obligations rather than portfolio tax management.

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Strategy’s Bitcoin position remains enormous. As of May 31, the company held 843,706 BTC acquired for an aggregate purchase price of $63.87 billion, implying an average purchase price of $75,699 per bitcoin. Against that position, the 32 BTC sale represents a negligible reduction in headline holdings, but it still breaks a long-running pattern in which Strategy’s Bitcoin disclosures were almost exclusively about accumulation.

The filing also shows that Strategy continued using its capital markets machinery during the same period.

Between May 26 and May 31, the company sold 801,994 shares of MSTR common stock under its at-the-market program, generating $128.3 million in net proceeds. As of May 31, Strategy listed $26.137 billion of remaining available issuance capacity for MSTR stock, alongside remaining preferred stock issuance capacity of $1.619 billion for STRF, $17.511 billion for STRC, $2.1 billion for STRK and $4.015 billion for STRD.

The Bitcoin sale lands against the backdrop of recent comments from Executive Chairman Michael Saylor and CEO Phong Le, who have both signaled in recent weeks that Strategy could sell BTC under certain circumstances. Saylor, however, has also emphasized that the company expects to buy more bitcoin than it sells, keeping the market focused on whether any isolated sale is offset by larger accumulation.

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That question remains open for the latest reporting period. On May 31, Saylor posted on X: “Working ₿etter.” The phrase appeared to tease another purchase, consistent with his usual cadence before formal Strategy updates. But no corresponding buy announcement had been made public at press time, leaving investors to wait for confirmation on whether the company bought more BTC than it sold during the period.

Strategy also disclosed that its US dollar reserve stood at $900 million as of May 31. The reserve, announced in December 2025, is a management-designated liquidity pool intended to support dividends on preferred stock and interest payments on outstanding debt. That reserve matters because it sits at the center of the company’s newer capital structure: Strategy has layered preferred equity, common stock issuance and Bitcoin holdings into a balance-sheet model that depends on continued access to liquidity.

The company’s board declared cash dividends payable on June 30 to holders of record as of June 15. The declared payments include $2.50 per share for STRF, $0.958333333 per share for STRC, €2.50 per share for STRE, $2.00 per share for STRK and $2.50 per share for STRD. Strategy also said the regular dividend rate on its variable-rate Series A Perpetual Stretch Preferred Stock, STRC, would remain at 11.50% per annum for monthly periods beginning on or after June 1.

At press time, BTC traded at $71,637.

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Bitcoin could retest the trendline breakout, 1-week chart | Source: BTCUSDT on TradingView.com
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Jake Simmons
Jake Simmons

Jake Simmons

Jake Simmons, a dedicated crypto journalist, has been passionate about Bitcoin since 2016 when he first learned about it. Through his extensive work with NewsBTC.com and Bitcoinist.com, Jake has become a trusted voice in the crypto community, guiding newcomers and seasoned enthusiasts alike towards a deeper understanding of this dynamic field.

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His mission is simple yet profound: to demystify Bitcoin and cryptocurrencies and make them accessible to everyone.
With a professional career in the Bitcoin and crypto scene that began right after graduating with a degree in Information Systems in 2017, Jake has immersed himself in the industry. Jake joined the NewsBTC Group in late 2022. His educational background provides him with the technical prowess and analytical skills necessary to dissect complex topics and present them in an understandable format. Whether you are a casual reader curious about Bitcoin or an investor seeking to navigate the latest market trends, Jake’s insights offer valuable perspectives that bridge the gap between complex technology and everyday usage.

Jake is not just a reporter on technological trends; he is a firm believer in the transformative potential of Bitcoin over traditional fiat currencies. To him, the current financial system is on the brink of chaos, propelled by unchecked government actions and flawed Keynesian economic policies. Drawing from the principles of the Austrian school of economics, Jake views Bitcoin not merely as a digital asset but as a crucial step towards rectifying a failing monetary system. His libertarian views reinforce his stance that just as the church was separated from the state, so too should money be freed from governmental control.

For Jake, Bitcoin represents more than just an investment; it's a peaceful revolution. He envisions a future where Bitcoin fosters a sustainable and responsible financial framework for generations to come. His advocacy is not about opposition but about evolution, about laying the groundwork for a system that prioritizes transparency and equity over secrecy and inequality.

As a journalist, Jake’s articles are crafted with the precision of a scholar and the passion of a true believer. He provides not only news but also thoughtful analysis that connects the dots between daily developments and larger economic theories. His work is a beacon for those lost in the technical jargon often associated with crypto discussions, illuminating the practical implications and benefits of these technologies.

In summary, Jake Simmons is not just reporting on a revolution; he wants to be part of it, fully committed to enhancing public understanding and adoption of Bitcoin and cryptocurrencies. His work is more than just a collection of articles; it’s a resource, a guide, and a companion for anyone ready to explore the potential of this digital frontier. Whether you are taking your first steps into crypto or are a veteran looking to stay on top of the latest trends, Jake’s insights provide clarity and foresight in an often unpredictable industry. Join him on this journey to reshape the world of finance, one post at a time.

You can engage with his latest takes on Twitter: @realJakeSimmons.

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Disclaimer: The information found on NewsBTC is for educational purposes only. It does not represent the opinions of NewsBTC on whether to buy, sell or hold any investments and naturally investing carries risks. You are advised to conduct your own research before making any investment decisions. Use information provided on this website entirely at your own risk.

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Reason to trust

Strict editorial policy that focuses on accuracy, relevance, and impartiality
Created by industry experts and meticulously reviewed
The highest standards in reporting and publishing
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