Saylor’s Strategy Safe from Liquidation, Says Willy Woo

Michael Saylor’s Strategy Safe from Liquidation, Says Willy Woo

Written by Aaron S.,

Editor-In-Chief

Last Updated: November 05, 2025

Key Takeaways

Willy Woo, a Bitcoin analyst, stated that Strategy is unlikely to sell any of its Bitcoin during the next major market downturn;
Strategy's $1.01 billion debt due on September 15, 2027, can be managed without selling Bitcoin if its stock stays above $183.19;
Woo cautioned that if Bitcoin rises too slowly in the 2028 bull run, partial liquidation could still occur.

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Bitcoin analyst Willy Woo shared his view that Strategy, led by Michael Saylor, is not at risk of selling its Bitcoin BTC $103,477.99 holdings during the next major market downturn.

In a November 5 post on X, Woo stated that a sell‑off by Strategy in the next bear market is doubtful.

He pointed out that the firm’s debt is mostly in convertible senior notes, which allow the company to settle its obligations through cash, shares, or a mix of both when the payments come due.

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One notable debt is about $1.01 billion, due on September 15, 2027. Woo explained that Strategy would avoid selling Bitcoin to meet this payment if its stock price remains above $183.19.

A market observer known as The Bitcoin Therapist stated that Bitcoin’s performance would have to deteriorate for Strategy to consider selling coins. They said it would require a long and severe bear market to trigger such an outcome.

Currently, Strategy holds about 641,205 Bitcoin, valued at roughly $64 billion, according to the latest data from Saylor Tracker.

Although Woo does not expect forced selling in the short term, he did add a caution for the longer term.

If Bitcoin does not rise fast enough during the anticipated 2028 bull market, he suggested there is a possibility of partial liquidation by Strategy.

Recently, Saylor explained that the company is not looking to buy other firms that hold Bitcoin on their balance sheets. Why? Read the full story.