Michael Saylor’s Strategy Inc. (NASDAQ: MSTR) has sparked fresh fears of Bitcoin (BTC) sales after transferring 411 BTC to Coinbase Prime on May 29. The transfer, valued at approximately $30.24 million at press time, was detected by on-chain analytics firm Arkham Intelligence. Coinbase Prime is an institutional-grade crypto prime brokerage backed by Coinbase Global Inc. (NASDAQ: COIN).

This move comes amid heightened scrutiny of Strategy’s Bitcoin holdings, which have been a cornerstone of the company’s corporate treasury strategy since 2020. Under Saylor’s leadership, MicroStrategy (rebranded as Strategy in 2025) accumulated over 250,000 BTC, making it the largest public corporate holder of Bitcoin. The company’s aggressive purchases during price spikes have created batches of coins purchased at high prices, often above $80,000.

CEO Phong Le hints at potential Bitcoin sales

During a Fox Business interview on May 28, Phong Le, CEO of Strategy, admitted that the company could sell some of its BTC to increase shareholder value in the long term. “Will likely sell Bitcoin at some point in time, but we will be net increasing our Bitcoin and, more importantly, increasing your Bitcoin per share,” Le stated. With BTC price having dropped below the company’s average cost basis of about $75,000, Le explained that the company could generate large unrealized tax losses on its books due to Bitcoin’s volatility.

Le elaborated that they can strategically sell portions of these higher-cost coins to realize those losses. Moreover, the move could provide valuable tax savings, thereby allowing the company to immediately repurchase more Bitcoin at the lower price and still end up with a net increase in holdings and a lower overall cost basis. This tax-loss harvesting strategy is common in traditional finance but relatively novel for Bitcoin corporate treasuries.

Prediction markets bet on Strategy selling BTC in 2026

Following the Coinbase Prime deposit, prediction market traders increased their bets that Strategy could sell Bitcoin before the end of 2026. Specifically, Polymarket traders are betting a 91% chance, up 68% over the last 24 hours, that Strategy could sell any BTC by December 31, 2026. This sentiment reflects growing uncertainty about the company’s long-term Bitcoin holding strategy, especially as regulatory and market conditions evolve.

The Polymarket contract shows a sharp increase in probability after the transfer was reported. Traders are factoring in both the tax-loss harvesting rationale and the possibility that Strategy may need liquidity for other corporate purposes. At press time, the company held approximately $871 million in cash reserves, following its recent early debt repayment, as reported by Finbold. However, the cash position may not be sufficient to cover future dividend obligations without tapping into Bitcoin holdings.

Historical context: Strategy’s Bitcoin journey

Strategy Inc., formerly MicroStrategy, began purchasing Bitcoin in August 2020 under the guidance of co-founder and executive chairman Michael Saylor. The initial purchase was 21,454 BTC for $250 million. Since then, the company has periodically increased its holdings through debt offerings, equity raises, and cash flow. Saylor has been a vocal advocate for Bitcoin as a store of value and a hedge against inflation.

The company’s Bitcoin holdings have been a double-edged sword. During bull markets, the value of the treasury skyrocketed, boosting the company’s stock price. However, during bear markets, the unrealized losses have weighed heavily on the balance sheet. In 2022, when Bitcoin plunged to around $16,000, the company faced margin calls on its loans secured by Bitcoin. Since then, Saylor has restructured the debt and reduced leverage.

In 2025, the company rebranded to Strategy Inc. to reflect its broader focus on digital asset strategies beyond just software. The move was seen as an attempt to distance the company from its legacy enterprise software business and embrace its identity as a Bitcoin treasury company.

Tax-loss harvesting: A smart play or a sign of weakness?

Le’s comments about tax-loss harvesting have drawn mixed reactions from analysts. On one hand, it is a standard financial practice that can offset capital gains and reduce tax liabilities. On the other hand, selling Bitcoin at a loss could be interpreted as a lack of conviction in the asset’s long-term appreciation. Some investors worry that if Strategy starts selling, it could trigger a broader sell-off in the market.

However, Le was careful to frame the potential sale as part of a net-positive strategy. By selling high-cost coins at a loss and immediately repurchasing cheaper coins, Strategy can lower its overall cost basis and increase its Bitcoin per share. This approach is similar to tax-loss harvesting in traditional portfolios, where investors sell losing positions to offset gains from winning positions.

The key difference is that Bitcoin is highly volatile, and the timing of such trades must be executed carefully to avoid triggering wash sale rules. In the U.S., wash sale rules apply to securities but not to cryptocurrencies, according to current IRS guidance. This gives Strategy more flexibility to repurchase Bitcoin shortly after selling.

Market impact and future outlook

The news of the Coinbase Prime deposit initially caused a minor dip in Bitcoin’s price, which dropped 1.5% to around $73,500. However, the market quickly recovered as traders digested the tax-loss harvesting explanation. Bitcoin has been trading in a range between $70,000 and $80,000 for most of May, with uncertainty about interest rates and regulatory developments weighing on sentiment.

Strategy’s stock (MSTR) also saw increased volatility. The stock closed down 2.3% on May 29, but has gained over 12% in the past month as investors anticipate the company’s next earnings report. The Q1 2026 earnings call, where Le first hinted at potential sales, was well-received, with the stock rallying afterward.

Looking ahead, Strategy’s Bitcoin strategy will continue to be a focal point for both crypto enthusiasts and traditional investors. The company’s ability to navigate the volatile crypto market while maintaining shareholder value will be closely watched. If Bitcoin prices recover, the tax-loss harvesting strategy may not be necessary. If prices continue to decline, however, more sales could be on the horizon.

Michael Saylor remains a Bitcoin maximalist, but the corporate reality of needing to generate returns for shareholders may force Strategy to adopt a more flexible approach. The 411 BTC move to Coinbase Prime could be just the beginning of a more active treasury management strategy. Only time will tell whether this marks a pivot away from the buy-and-hold approach that defined Saylor’s tenure.

Source:Finbold News