MSTR down 47.5%, ranked sixth. Is it bad? Schiff vs Saylor: The Investment Philosophy Clash

Economist Peter Schiff recently tweeted about MicroStrategy (MSTR), stating that if the company were included in the S&P 500 index, its 47.5% decline by 2025 would rank as the sixth-worst performance among the index’s stocks. This comment has reignited the debate between Schiff and MSTR CEO Michael Saylor regarding corporate Bitcoin purchasing strategies.

What is Schiff’s criticism based on?

The logic behind the specific numbers

Schiff pointed out that MSTR’s 47.5% decline by 2025 would rank as the sixth-worst in the S&P 500. His core criticism is: Saylor claims that the best choice for companies is to buy Bitcoin, but in reality, this approach damages shareholder value.

It should be clarified here—MSTR is not currently included in the S&P 500 index; Schiff’s comment is a hypothetical comparison. He uses this assumption to illustrate that, by the standards of the S&P 500, MSTR’s performance would be among the worst.

The logic behind the criticism

Schiff is a long-term gold supporter and believes:

• MSTR heavily invests company funds into Bitcoin, effectively using shareholders’ money on high-risk assets
• Although Bitcoin’s price could rise significantly by 2025, MSTR’s stock performance lags far behind Bitcoin’s gains
• This suggests that the company’s other business operations or financing costs may be dragging down overall performance

Why does Saylor still stick to his strategy?

What the latest holdings data indicates

According to the latest news, on December 29, 2025, MSTR purchased an additional 1,229 Bitcoins at an average price of $88,568. The company’s total holdings now reach 672,497 BTC, with an average cost of $74,997. At current prices, this results in an unrealized profit of about 15%.

This data highlights two key points:

• Saylor is indeed steadfast in executing the “dollar-cost averaging into Bitcoin” strategy, unaffected by short-term stock price fluctuations
• From the perspective of Bitcoin holdings cost basis, this strategy is profitable in terms of Bitcoin assets

Timing is crucial

The information mentions that Matt Cole, CEO of Strive, once calculated that MSTR’s annualized return over the past five years was only 3%, which seems less attractive than gold. However, he also pointed out that MSTR’s total return over the past five years has outperformed Bitcoin and gold.

What does this imply? The key is the time period you consider. Saylor’s strategy is long-term dollar-cost averaging, not concerned with short-term stock price volatility. His logic is: as long as Bitcoin appreciates over the long term, holding enough Bitcoin will generate returns.

Fundamental differences between two investment philosophies

This is not just a debate about MSTR but a confrontation between two different investment philosophies: one believes companies should operate prudently to protect shareholders, the other advocates bold allocation of future assets.

The market’s true reaction

Interestingly, despite Schiff’s criticism, Saylor continues to buy. This reflects the market’s real attitude toward this strategy—supporters see it as visionary, opponents see it as gambling.

MSTR’s 47.5% decline by 2025 is indeed not ideal, but it’s important to note that this decline reflects both Bitcoin’s volatility and the impact of the company’s financing costs and other business factors. Using stock price performance alone to dismiss the entire strategy may overlook the appreciation of Bitcoin assets themselves.

Summary

Schiff’s criticism is supported by data; MSTR’s stock performance by 2025 is indeed poor. But Saylor’s strategic logic is also clear—he bets on Bitcoin’s long-term appreciation, not short-term stock performance. The core of this debate is not about who is right or wrong but about two fundamentally different investment frameworks. For investors, the key is to understand which logic they support, rather than being swayed by a single viewpoint.