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Reading: Strategy Sells Bitcoin for First Time Since 2022, Triggering $15M Polymarket Dispute
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Bitcoin

Strategy Sells Bitcoin for First Time Since 2022, Triggering $15M Polymarket Dispute

News Desk
Last updated: June 1, 2026 7:43 pm
News Desk
Published: June 1, 2026
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A recent filing by Strategy has revealed that the company sold 32 Bitcoin for approximately $2.5 million, a transaction that accounts for a mere 0.004% of its vast holdings of 843,706 BTC. This sale occurred between May 26 and May 31, with the average selling price pegged at $77,135 per coin. The intent behind this sale is explicitly stated: the funds will be used to meet preferred stock dividend obligations.

Despite the relatively small amount sold, this transaction highlights significant dynamics within Strategy’s capital structure. As of May 31, the company had previously purchased its Bitcoin at an average cost of $75,699 per coin, meaning the recent sale yielded a profit. The total Bitcoin treasury of Strategy sits near $63.87 billion, indicating that the sale, although arithmetically negligible, affirms the increasing capital obligations the company is facing.

An overview of Strategy’s preferred stock, known internally as STRC or Stretch, reveals that it has ballooned to $8.5 billion in only nine months, making it the largest preferred stock by market capitalization globally. To date, Strategy has raised a total of $5.6 billion in gross proceeds from STRC and has maintained a consistent record of dividend payments, totaling over $693 million across 23 distributions since early 2025. The STRC holds an annualized dividend rate of 11.5%, compelling the company to continually generate returns, primarily through additional Bitcoin acquisitions.

CEO Michael Saylor has articulated that Strategy needs Bitcoin to appreciate at a minimum of 2.3% per year to sustain these dividend obligations indefinitely without resorting to additional common stock sales. He has also indicated that for every Bitcoin sold, the company intends to purchase an additional 10 to 20, framing this recent sale as a necessary step in a larger acquisition strategy.

The sale has triggered a significant dispute in the prediction market Polymarket, where Bettors have split on the legitimacy of the timing of the sale regarding contract settlements. The confusion stems from the fact that, although the announcement occurred on June 1, the transaction took place during the specified window prior to this date. As a result, a $15 million resolution dispute has arisen, with market participants debating whether the on-chain timestamps substantiate the sale’s qualifying status.

In the backdrop of this transaction, Strategy is also advocating for increased dividend payment frequency for STRC, suggesting a shift to a semi-monthly distribution schedule. This strategic move aims to bolster STRC’s appeal, but critics argue that it could impose additional strain on the capital base. Competing preferred stocks, such as Strive’s SATA, have emerged with a higher 13% dividend rate, challenging STRC’s standing in the market.

The recent Bitcoin sale punctuates the company’s first disclosed reduction of its Bitcoin holdings since December 2022 and marks a shift from Saylor’s previous “never sell” philosophy to a more flexible approach of being a “net accumulator” of Bitcoin. This change in strategy may evoke concerns among investors regarding the potential for further Bitcoin sales to meet mounting STRC dividend obligations in the future, a development that markets are increasingly factoring into their predictions. As sentiment in the market reacts, Bitcoin prices dipped to around $71,000, with shares of MSTR experiencing a drop of approximately 6%.

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