On March 31, 2025, the company known as Strategy (previously MicroStrategy) acquired $2 billion in Bitcoin, increasing its total holdings to 528,185 BTC, which accounts for more than 2.5% of the entire Bitcoin supply. Michael Saylor, the face of Strategy, is often hailed as the foremost Bitcoin advocate, yet some view him as a potential liability to the network.
Michael Saylor: A Controversial Figure
During the 2020s, Saylor emerged as a leading proponent of Bitcoin. His enterprise ranks among the top 10 holders of Bitcoin, consistently investing millions and billions into BTC. Beyond boosting the corporate Bitcoin reserves and promoting the stock of Strategy, Saylor is active on social media, sharing insights about the significance of Bitcoin for various stakeholders, including governments, institutions, and individuals. He has also been known to engage with U.S. officials regarding Bitcoin and has expressed a willingness to collaborate on cryptocurrency regulations with the Trump administration.
Saylor’s mission is to familiarize financial institutions and large investors with Bitcoin, offering them an on-ramp to the digital asset through the company’s stock. He emphasizes that Bitcoin is a form of capital, drawing parallels to Manhattan real estate and gold, highlighting its advantages of storage, transportability, and transaction ease. His straightforward strategy revolves around accumulating as much Bitcoin as possible, and he has urged the U.S. government to adopt this approach as well.
The race for Bitcoin, fueled by Saylor’s activities and advocacy, is underway. According to Architect Partners, about 25% of public companies may incorporate BTC into their balance sheets by 2030, with several governments already holding Bitcoin.
Saylor’s methodology toward Bitcoin deviates from its foundational ethos of inclusivity, appearing to support the dominance of U.S. banks within the global economic landscape. A critical article points out the tension between Bitcoin’s anti-bank origins and Saylor’s aim to assist financial institutions in leveraging it.
Critics argue that Bitcoin was intended to serve as an independent digital currency, distinctly separate from the U.S. dollar. By framing Bitcoin as capital rather than money and encouraging relentless accumulation by the U.S. government alongside the global push for USD-pegged stablecoins, Saylor appears to undermine the original purpose of Bitcoin.
In this context, Strategy’s escalating influence and Bitcoin concentration occupy a complex position. On one hand, it advocates for cryptocurrency and broadens access to alternatives when traditional banking and fiat currencies falter. Conversely, it may also be seen as reinforcing the same institutions Bitcoin was designed to challenge.
Some critics express concern that Saylor’s prominent role positions him as a de facto “leader” of Bitcoin, a framework contrary to the decentralized nature envisaged by its creator’s anonymity. They worry that his personal perspectives and influence could overshadow Bitcoin’s foundational principles.
Beyond philosophical debates, there exists a palpable fear that Saylor might one day drastically impact Bitcoin’s price, leading to a sharp decline; others are concerned about the concentrated ownership of such a substantial amount of Bitcoin within a single corporate entity.
Many ponder the implications if Bitcoin were to plummet before Saylor executes a sale. He has publicly stated his intention to never sell, even humorously suggesting that he wants his private keys destroyed after his passing.
Despite his iconic status among certain crypto circles, distrust persists due to the checkered history of Strategy.
Saylor’s and Strategy’s Legal Challenges
Founded in 1998, Strategy saw its stock soar dramatically in 2000, climbing from $7 to $333 within that year before plummeting 62% in a single day. Following the dot-com bubble burst, the company was forced to restate its financial results, admitting to over-reporting revenues for 1998 and 1999 by $66 million. The stock fell further after it announced additional restatements for 1997, bottoming out at $33 by April 2000. This tumultuous period resulted in a lawsuit and penalties totaling $10 million, with personal fines levied against top executives. Nevertheless, the company rebounded to prominence in the ensuing years.
In 2022, the Attorney General took Saylor to court for alleged tax evasion. The case was settled in 2024 with an astonishing $40 million tax recovery. Saylor was accused of trying to project a false residency in Florida or Virginia, states with lower personal income taxes, while actually living in D.C. The Attorney General claimed Saylor boasted about his tax evasion tactics. Saylor maintained that he resided in Florida, but these legal issues have eroded some trust within the crypto community.
Is Strategy’s Bitcoin Holdings a Double-Edged Sword?
Skepticism surrounding Saylor extends to doubts about the reality of Strategy’s massive Bitcoin purchases. Some highlight the price drops that follow significant acquisitions as signs that these transactions may not be genuine. Questions arise about the sources from which Strategy acquires such large quantities of Bitcoin, with calls for transparency regarding the company’s wallet addresses.
Arkham Intelligence has identified 96% of Strategy’s Bitcoin addresses, confirming that custodians like Coinbase Prime and Fidelity manage them. This alleviates some doubts regarding their Bitcoin holdings. However, lingering concerns remain: the company’s substantial Bitcoin reserve now looms like a sword of Damocles over the market.
Let’s address the prevailing fear of a major sell-off. Should Strategy ever decide to unload its Bitcoin, it could severely disrupt the overall market.
While the idea of a large sell-off seems unlikely for the company, Saylor has expressed bullish predictions about Bitcoin’s future value. However, some assert that there’s more to his strategy than merely betting on the asset’s appreciation, given the complexity of his business model. Since Bitcoin is central to this model, selling would appear counterintuitive. Still, the specter of forced liquidation remains a genuine concern.
The company has been increasing its debt to facilitate further Bitcoin purchases through convertible notes that attract other investors. This strategy allows Strategy to amass even more capital. However, as the market matures and Bitcoin’s price rises, acquiring additional Bitcoin becomes increasingly difficult, while liquidity may diminish as large holders, including miners and corporations, opt to hold rather than sell. This could pose challenges for the future of Strategy’s Bitcoin-centric strategy.
At present, Strategy holds $44 billion in Bitcoin against $8.2 billion in debt. The first quarter of 2025 represented the worst performance for crypto in seven years, and MSTR stock has shown high volatility. Nevertheless, analysts predict that it would take a significant 50% drop in Bitcoin’s price by 2027 to deter MSTR investors from Strategy, potentially prompting a sell-off.
Saylor minimizes the likelihood of forced liquidation, stating that if Bitcoin were to fall to $1, Strategy would buy up all available bitcoins. He holds over 46% of the voting rights, giving him substantial control to withstand any potential liquidation. Ultimately, the reality of the threat will become clearer by 2027 when the first batch of convertible notes reaches maturity.
Despite the uncertainty, many Bitcoin enthusiasts maintain an optimistic outlook. They argue that even if Saylor were to sell off his holdings, they would simply purchase discounted BTC and move forward, asserting that no single entity can undermine Bitcoin.