Bitcoin

SkyBridge founder and former Trump advisor Anthony Scaramucci is standing firmly behind Michael Saylor, dismissing a wave of predictions earlier this summer that Strategy's <a href="https://www.thestreet.com/crypto/bitcoin" rel="noopener noreferrer nofollow">Bitcoin</a>-heavy balance sheet was headed toward liquidation.
In a <a href="https://x.com/Scaramucci/status/2071345399915291053" rel="noopener noreferrer nofollow">post on X</a> early Monday, Scaramucci took aim at those who had publicly bet against Saylor's strategy.&nbsp;
<blockquote>
 "Not a billionaire but you should think about not being left behind," Scaramucci wrote, framing the moment as a test of conviction rather than a vindication of the bears.
</blockquote>
He went further, posing a pointed question to the market: how many people will later claim credit for having capitalized on the "Michael Saylor is going to get liquidated" narrative that circulated in early summer 2026.
<h2 id="i-ride-with-saylor">"I ride with Saylor"</h2>
Scaramucci closed his post with a simple statement of allegiance: "I ride with Saylor." The remark places him squarely on one side of an increasingly <a href="https://www.thestreet.com/crypto/markets/michael-saylor-reveals-key-reason-for-bitcoins-crash" rel="noopener noreferrer nofollow">public debate</a> over whether Strategy's debt-funded Bitcoin accumulation model is sustainable through periods of sharp price weakness.
<a href="https://www.thestreet.com/crypto/markets/analyst-reveals-the-simple-rule-that-could-help-you-survive-any-crypto-downturn" rel="noopener noreferrer nofollow">Related: Analyst reveals the simple rule that could help you survive any crypto downturn</a>
This isn't the first time Scaramucci has used his platform to push back against bearish narratives surrounding <a href="https://www.thestreet.com/crypto/investing/ex-trump-advisor-makes-a-bold-5-point-case-for-bitcoin" rel="noopener noreferrer nofollow">Bitcoin and Strategy</a> specifically.
He has repeatedly argued that periods of maximum pessimism tend to mark turning points rather than confirmations of deeper structural problems, a framework he has applied to Bitcoin's price action broadly in recent weeks.
<h3 id="popular-on-thestreet-roundtable">Popular on TheStreet Roundtable:</h3>
<ul>
 <li><a href="https://www.thestreet.com/crypto/markets/analyst-sends-blunt-message-on-elon-musks-bitcoin-ties" rel="noopener noreferrer nofollow">Analyst sends blunt message on Elon Musk's Bitcoin ties</a></li>
 <li><a href="https://www.thestreet.com/crypto/markets/anthony-scaramucci-unveils-bitcoin-target-for-july" rel="noopener noreferrer nofollow">Ex-Trump advisor unveils new Bitcoin price target</a></li>
 <li><a href="https://www.thestreet.com/crypto/markets/analyst-issues-bold-call-on-cathie-woods-favorite-crypto-stock" rel="noopener noreferrer nofollow">Analyst issues bold call on Cathie Wood's favorite crypto stock</a></li>
</ul>
His latest comments arrive against a backdrop of renewed scrutiny over Strategy's balance sheet, with several market voices questioning whether the company's debt structure could come under strain if Bitcoin's price stayed depressed for an extended period.
<h2 id="a-test-saylor-has-faced-before">A test Saylor has faced before</h2>
Liquidation concerns are not new territory for Saylor or Strategy. The company has weathered similarly intense scrutiny during past Bitcoin drawdowns, including a stretch in 2022 when its debt briefly <a href="https://www.thestreet.com/crypto/markets/analyst-sends-blunt-message-on-elon-musks-bitcoin-ties" rel="noopener noreferrer nofollow">exceeded the combined value</a> of its Bitcoin and cash holdings.
Whether the early-summer 2026 predictions prove similarly premature remains to be seen, but for now, Scaramucci's message is unambiguous: he isn't betting against Saylor.
<a href="https://www.thestreet.com/crypto/markets/bitcoin-demand-is-gone-for-46-days-heres-what-this-analyst-says-investors-should-know" rel="noopener noreferrer nofollow">Related: Bitcoin demand is gone for 46 days, here's what this analyst says investors should know</a>

Ex-Trump advisor sends a bold message to Saylor's haters

Table of Contents

TheStreet Roundtable

Other articles published on Jun 29, 2026

Join our free newsletter for daily crypto updates!