From ‘Never Sell’ to Maybe Sell? Saylor’s Strategy Filing Changes Bitcoin Tune

Strategy, formerly MicroStrategy, may be preparing to offload part of its extensive Bitcoin (BTC) holdings as it faces growing financial pressures.

According to a recent U.S. SEC filing, the company, led by Michael Saylor, faces a complex mix of declining Bitcoin prices, growing debt, and weakening cash flow.

What Did Strategy Disclose to the SEC?

In an 8-K report to the SEC, Strategy revealed it might be forced to sell Bitcoin if it cannot secure new equity or debt financing.

The document noted that unfavorable market conditions could force the sale of Bitcoin below its original purchase cost for some tranches, and that proceeds might be needed to meet current financial obligations.

The company currently holds 528,185 BTC, valued at over $40 billion, purchased at an average price of $67,458 per coin. However, due to price fluctuations during the period, Strategy expects to report an unrealized loss of nearly $6 billion for the first quarter of 2025.

Why Might Strategy Need to Sell BTC?

Strategy’s financial commitments reportedly include $8.2 billion in outstanding debt, $35 million in annual interest payments, and $150 million in preferred dividend obligations.

In March, the firm attempted to raise $2.1 billion via a perpetual preferred stock offering yielding 8%. The goal was stated as supporting operations and possibly adding to Bitcoin holdings, but the outcome of this fundraising effort remains unclear.

According to the reports, selling 2,318 BTC could address short-term liquidity needs. However, larger repayments could require liquidating up to 12,800 BTC. While a full selloff of holdings is not anticipated, the SEC filing suggests the possibility cannot be ruled out.

How Does Market Weakness Play In?

Bitcoin’s recent price drop earlier this week has added further strain, though it is now trading in the volatile period at around $82,000.

External factors, including market reactions to U.S. trade policy developments like new tariffs discussed by President Donald Trump, have weighed on investor sentiment. Despite this weakness, some analysts maintain longer-term projections for a potential Bitcoin recovery toward $110,000, possibly linked to future global interest rate cuts.

Michael Saylor has consistently maintained a “Never sell” position on Bitcoin, framing the company’s strategy as a long-term hedge against inflation. However, the latest disclosures signal that financial realities may now challenge that stance.