Peter Schiff, Wall Street's most vocal Bitcoin skeptic, is back with his strongest criticism yet of Michael Saylor and Strategy (MSTR). In a recent X post, Schiff didn't just question the company's Bitcoin accumulation strategy—he called it a fraud and declared Saylor "the biggest con man on Wall Street."

The core of Schiff's argument? Strategy is approaching collapse because it's caught in an unsustainable financial loop. According to Schiff, Saylor was recently forced to sell company stock not to acquire more Bitcoin (BTC), but simply to raise cash for interest payments and dividend obligations. Since Strategy generates virtually no meaningful operating income, the only way it can continue paying dividends is by issuing more preferred shares at rates between 8% and 10%—unless it starts selling Bitcoin.

Schiff described this structure as Ponzi-like, arguing that the model is fundamentally "broken." He also criticized mainstream financial media for giving Saylor positive coverage and urged investors to approach celebrity CEOs with skepticism.

MarketDash reached out to Strategy for comment but did not receive a response.

This isn't new territory for Schiff. He's long maintained that gold is objectively superior to Bitcoin, citing its physical properties and industrial applications. Bitcoin, in his view, is "purely subjective" with no real-world utility. He pointed to Bitcoin's recent decline even as gold rallies and the NASDAQ hovers near all-time highs, framing this as investors rotating out of what he calls a "fake asset" into tangible commodities.

Meanwhile, data from CryptoQuant tells a different story. Strategy currently holds 649,870 BTC, valued at more than $48.3 billion—up significantly from under 500,000 BTC in January 2025. Whether that's visionary accumulation or reckless leverage depends entirely on who you ask.