Bitcoin News Today: Bitcoin Billionaire Saylor's High-Stakes Bid for S&P 500 Glory

Michael Saylor, the chairman of Strategy Inc., has made a significant breakthrough by cracking the Bloomberg 500 list, marking a key milestone for the entrepreneur and his company. Saylor, who has become a prominent figure in the Bitcoin investment space, has turned Strategy from an enterprise software firm into one of the largest corporate Bitcoin holders. The company now holds 636,505 Bitcoin, valued at approximately $70.6 billion, and has seen a 50.5% return on investment based on its average purchase cost of $73,765 per Bitcoin [2]. This strategic shift has not only transformed Saylor into a Bitcoin billionaire but has also positioned Strategy as a potential contender for inclusion in the S&P 500 index.

Saylor’s aggressive capital-raising efforts have allowed the company to build a balance sheet with roughly $70 billion in Bitcoin. His strategy has drawn comparisons to Elon Musk and Tesla, with Max Keiser, a well-known Bitcoin advocate, highlighting how Saylor’s ability and financial engineering have driven investor confidence in MSTR stock. Keiser argues that investors are buying the “jockey, not the horse,” echoing the speculative nature of Tesla’s valuation based on belief in Musk’s vision [3]. Strategy’s diluted market capitalization has reached $105 billion, with an mNAV ratio of 1.48, far outpacing other Bitcoin treasury companies like MARA Holdings, which has a diluted mNAV ratio of only 1.04 [3].

The company's financial performance, while volatile, has met key metrics for index eligibility. Strategy reported a $14 billion unrealized gain in the most recent quarter, meeting the profitability requirements for S&P 500 inclusion under current rules. According to Stephens Inc., if Strategy is added to the index, passive funds tracking it would be required to purchase approximately 50 million shares, valued at around $16 billion at current prices [2]. This would represent a significant validation of Saylor’s strategy and could indirectly bring Bitcoin exposure to institutional investors such as pension funds.

However, inclusion in the S&P 500 is not guaranteed. The S&P committee evaluates not only financial metrics but also liquidity, sector balance, and market stability. While Strategy has met or exceeded key criteria—including a market capitalization of $94.82 billion and a float-adjusted liquidity ratio that ranks highest among potential candidates—the company's high volatility remains a concern for index gatekeepers. Strategy’s 30-day price swings are at 96%, exceeding those of major tech firms like Nvidia and Tesla [2]. This volatility has led to skepticism about the sustainability of the corporate-treasury model Saylor pioneered, which involves selling debt and equity to buy and hold Bitcoin.

Despite these challenges, Saylor's company has already been included in the Nasdaq 100, and the potential addition to the S&P 500 would represent a broader institutional acceptance of the digital-asset class. The S&P committee's recent inclusion of Coinbase Global Inc. and Block Inc. signals an ongoing recognition of crypto's growing footprint in the financial markets. As the debate continues over the merits of corporate Bitcoin holdings, Saylor remains a central figure in shaping the narrative. His inclusion in the Bloomberg 500 underscores not just the financial success of his strategy, but the increasing influence of Bitcoin in the global financial system.

Source:

[1] MSTR Stock Quote Price and Forecast (https://www.cnn.com/markets/stocks/MSTR)

[2] Bitcoin faithful bet on Saylor's Strategy being added to S&P 500 (https://fortune.com/crypto/2025/09/04/bitcoin-michael-saylor-sp-500-strategy-microstrategy/)

[3] Why Max Keiser Thinks Michael Saylor Has Become ... (https://u.today/why-max-keiser-thinks-michael-saylor-has-become-bitcoins-elon-musk)

[4] Bitcoin Faithful Bet on Saylor's Strategy Being Added to S&P 500 (https://finance.yahoo.com/news/bitcoin-faithful-bet-saylor-strategy-143009749.html)