Saylor continues to acquire Bitcoin at local peaks despite increasing risks.

Strategy (previously MicroStrategy) has established a pattern of conducting its weekly Bitcoin purchases near local peaks in recent weeks.

On Nov. 10, CryptoQuant analyst JA Marturn observed that the firm’s latest acquisition announcement from Michael Saylor followed a similar trend.

As per an SEC filing, Strategy revealed 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 leading asset traded mostly sideways throughout the past week, Bitcoin had reached a high of over $106,000 on Nov. 3 before declining more than 9% to briefly trade below $100,000. It continues to contend with the $106,400 support-turned-resistance and the $100,000 local floor.

Bitcoin price movements (Source: TradingView)

However, Saylor’s firm did not manage to purchase at the market bottom. Instead, the acquisitions occurred at one of the highest prices the leading asset traded at last week.

This aligns with the firm’s previous purchases, which have coincided with short-term peaks, raising the question of why the firm continues to “buy the top.”

Strategy’s Bitcoin Purchases Near Local Tops (Source: CryptoQuant)

While the consistency of this visual pattern creates an impression of poorly timed execution, it only represents part of the overall picture.

Why Strategy tends to buy into BTC strength

Strategy’s acquisitions typically cluster around times of heightened liquidity for reasons not related to market enthusiasm.

The firm’s corporate treasuries allocate capital at specific intervals, such as following equity sales, convertible issuances, or internal liquidity events.

These opportunities seldom coincide with discounted market conditions. Instead, they often arise during periods when Bitcoin is trading with deeper order books and reduced execution risk.

Market analysts have pointed out that this structural reality clarifies why Strategy’s entries frequently align with local highs. Large corporate orders are executed when market depth is at its strongest, which generally corresponds with rallies rather than downturns.

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

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

Saylor has consistently positioned Bitcoin as a long-duration monetary instrument, and the firm’s operations adhere to that principle. The goal is consistent exposure, not precise timing.

Thus, the firm’s execution windows are determined by corporate processes, prioritizing consistent accumulation over opportunistic entry.

Long-term performance vs. structural risks

Over a longer timeframe, critiques of Strategy’s timing diminish in significance.

Since Strategy commenced its Bitcoin purchases in 2020, its treasury has evolved into one of the most lucrative corporate asset allocations in contemporary history.

The company currently holds 641,692 BTC, valued at approximately $68 billion, which was acquired at an average price of $106,000, resulting in a total cost basis of $67.5 billion. At current valuations, that position suggests roughly $20.5 billion in unrealized gains.

Even more notable, Strategy has generated over $12 billion in Bitcoin gains year-to-date in 2025, despite reducing its pace of accumulation to a few hundred coins in recent weeks.

Strategy’s Bitcoin Holdings Key Metrics (Source: Strategy)

This presents a paradox at the core of the Saylor strategy: the entries may appear unfavorable, but the outcomes are remarkable. It reflects a corporate dollar-cost averaging approach on a structural timeline.

Short-term volatility enhances the perception that Strategy buys at peaks; the multi-cycle reality indicates that those “tops” often evolve into highly profitable entries over time.

A broader comparison underscores this point. Over the past year, Strategy’s equity (MSTR) has exhibited 87% volatility, significantly 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 transformed that volatility into asymmetric upside.

However, strong returns do not shield the company from structural vulnerabilities. Barchart data reveals 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.

Strategy’s MSTR Price Performance Over the Past 2 Decades. (Source: Barchart)

Furthermore, some analysts contend that Strategy’s reliance on capital markets introduces significant risks if the cryptocurrency enters a prolonged downturn.

These 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 had no interest-bearing debt and had years before its earliest bond maturities. Thus, 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 substantial decline in MSTR’s share price, which is historically plausible given the stock’s drawdowns of 70–80% in previous cycles, would restrict the company’s flexibility and heighten the likelihood of dilutive capital issuances.

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

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

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

As a result, skeptics have pointed out that the model resembles a leveraged carry trade with limited margin for error. In fact, some have characterized the process as “Ponzi-like,” arguing that the firm’s liabilities are increasing faster than its operating income.

According to them, this leaves Strategy reliant on either rising Bitcoin prices or sustained investor interest in high-yield instruments.

Signal power and narrative strategy

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

Thus, Strategy’s buying into strength reinforces the notion 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 moments of market hesitation, the filings help stabilize sentiment by demonstrating consistent institutional demand.

This has enabled Strategy to effectively position itself as the market’s most reliable large-scale buyer, and its disclosures fulfill both operational and symbolic functions.

This dual role clarifies 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 attract criticism, particularly during periods of heightened volatility. Nevertheless, the framework guiding the purchases remains steady: Strategy is not positioning for the next quarter, but for the next decade.

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