Buy high, sell never: Saylor keeps buying Bitcoin at local tops despite mounting risk

Strategy (formerly MicroStrategy) has earned a reputation for making its weekly Bitcoin acquisitions near the local top in recent weeks.

On Nov. 10, CryptoQuant analyst JA Marturn noted that the firm’s most recent acquisition disclosure from Michael Saylor followed the same script.

According to an SEC filing, Strategy announced that it had acquired 487 BTC between Nov. 3 and Nov. 9 for $49.9 million at an average price of $102,557 per coin.

While the flagship asset spent most of the past week trading sideways, Bitcoin had reached a high of above $106,000 on Nov. 3 before sliding more than 9% to trade briefly below $100,000. It continues to battle with the $106,400 support-turned-resistance and the $100,000 local floor.

However, Saylor’s firm was unable to buy at the market bottom. Instead, the purchases arrived at one of the highest prices the top asset traded last week.

This is consistent with the firm’s previous purchases, which coincided with short-term peaks, and raises the question of why the firm continues to “buy the top.”

While the consistency of this visual pattern fuels an impression of mistimed execution, it tells only part of the story.

Why Strategy tends to buy into BTC strength

Strategy’s purchases tend to cluster around moments of elevated liquidity for reasons unrelated to market enthusiasm.

The firm’s corporate treasuries deploy capital at specific points, such as after equity sales, convertible issuances, or internal liquidity events.

These windows rarely align with discounted market conditions. Instead, they often open during periods when Bitcoin is trading with deeper order books and lower execution risk.

Market analysts have noted that this structural reality explains why Strategy’s entries often align with local highs. Large corporate orders are executed when market depth is strongest, which typically corresponds with rallies rather than periods of drawdown.

As a result, acquisition filings can create an optical illusion of systematically buying at peaks, even when the timing is set by liquidity availability and internal controls rather than sentiment.

For Strategy, the marginal price of a given tranche is secondary.

Saylor has consistently framed Bitcoin as a long-duration monetary instrument, and the firm’s operations follow that doctrine. The objective is steady exposure, not precision timing.

So, the firm’s execution windows are defined by corporate processes, and consistency of accumulation is prioritized over opportunistic entry.

Long-term performance vs. structural risks

Over a longer horizon, criticisms of Strategy’s timing lose some force.

Since Strategy began buying Bitcoin in 2020, its treasury has grown into one of the most profitable corporate asset allocations in modern history.

The company now holds 641,692 BTC, valued at approximately $68 billion, which was purchased at an average price of $106,000, resulting in a total cost basis of $67.5 billion. At current prices, that position implies roughly $20.5 billion in paper gains.

Even more striking, Strategy has generated over $12 billion in Bitcoin gains in YTD 2025, despite slowing its pace of accumulation to a few hundred coins in recent weeks.

This is the paradox at the heart of the Saylor strategy: the entries look poor, but the results are exceptional. It shows a corporate dollar-cost averaging on a structural timeline.

Short-term volatility amplifies the impression that Strategy buys tops; the multi-cycle reality shows that those “tops” often become deeply profitable entries over time.

A broader comparison emphasizes the point. Over the past year, Strategy’s equity (MSTR) has shown 87% volatility, sharply higher than Bitcoin’s 44%, and more volatile than the company’s other digital-asset products.

Yet despite this intensity, the cumulative exposure to Bitcoin has turned that volatility into asymmetric upside.

However, the strong returns do not immunize the company from structural vulnerabilities. Barchart data shows that a $10,000 investment in MSTR during the dot-com peak would be worth $7,207 today, illustrating two decades of volatility independent of the Bitcoin strategy.

Moreover, some analysts argue that Strategy’s dependence on capital markets introduces material risks if the cryptocurrency enters a multi-year downturn.

Those concerns have intensified as the company’s balance sheet has evolved.

Chris Millas, an advisor at Mellius Bitcoin, Brazil’s first Bitcoin treasury firm, noted that during the last bear market, the firm carried no interest-bearing debt and had years before its earliest bond maturities. So, its equity volatility was painful but had a limited operational impact.

However, this cycle is different. Strategy now holds interest-bearing obligations that must be serviced regardless of market conditions.

Millas argued that a severe drop in MSTR’s share price, which is historically plausible given the stock’s drawdowns of 70–80% in prior cycles, would limit the company’s flexibility and increase the likelihood of dilutive capital issuances.

According to him, that dilution, in turn, could pressure the stock further, creating a feedback loop that magnifies downside risk.

Indeed, Strategy faces roughly $689 million in interest payments due in 2026. Without new capital, the company cannot meet that obligation.

Moreover, recent fundraises highlight how financing conditions have shifted, with preferred-share offerings pricing yields around 10.5%, above the initial guidance of near 10%. The widening spread signals that capital is becoming more expensive, complicating the economics of debt-funded Bitcoin accumulation.

Due to this, skeptics have pointed out that the model resembles a leveraged carry trade with limited margin for error. In fact, some have labeled the process “Ponzi-like”, while arguing that the firm’s liabilities are growing faster than operating income.

According to them, this leaves Strategy dependent on either rising Bitcoin prices or continued investor appetite for high-yield instruments.

Signal power and narrative strategy

Even with these risks, Strategy’s purchases continue to exert outsized narrative influence. The company files frequent and transparent disclosures, and its visibility allows the acquisitions to function as a form of market signaling.

So, Strategy’s buying into strength reinforces the message that Bitcoin is a long-term monetary asset rather than a timing-sensitive trade.

Moreover, as several of Strategy’s higher-price filings in recent weeks have coincided with periods of market hesitation, the filings contribute to stabilizing sentiment by demonstrating steady institutional demand.

This has allowed Strategy to effectively position itself as the market’s most consistent large-scale buyer, and its disclosures serve both operational and symbolic purposes.

This dual role explains why Saylor continues to accumulate through short-term peaks.

For Strategy, the purchase price of any given week is secondary to the multi-year trajectory of both Bitcoin and the company’s identity as its largest corporate holder.

The optics may draw criticism, especially during periods of elevated volatility. Still, the framework guiding the purchases remains consistent: Strategy is not positioning for the next quarter, but for the next decade.

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