MicroStrategy’s S&P 500 Dream: Will Michael Saylor Finally Make Corporate Crypto History?

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If ever there was a spectacle to rival the Oxford and Cambridge boat race—or perhaps a particularly desperate fox hunt—it is the sight of Michael Saylor, maven of MicroStrategy (or, as it now prefers in a flourish of incisive corporate minimalism, “Strategy”), careering towards the S&P 500 like a cryptographically-emboldened Don Quixote. The man has staked his company’s reputation, its treasury, and perhaps the very GDP of several small nations, upon the surly moods of Bitcoin. 😏

“91% chance of $MSTR qualifying for S&P in 6 days.”
— Jeff Walton (@PunterJeff), June 24, 2025

So pronounces the mystic augur Jeff Walton, a keen-eyed analyst of markets and—one suspects—of racetrack odds. Walton’s revelation depends upon Bitcoin’s dainty toes remaining above $95,240 through June 30. With Bitcoin now sashaying about at $106,044, one might think the coast is clear. But, as in all things both financial and English, disaster looms best when least expected.

Walton, whose devotion to both YouTube and arcane earnings spreadsheets is to be commended, warns: should Bitcoin trip and fall more than 10% in some unscheduled pratfall before Q2 demurely closes its doors, Strategy’s mathematic waltz through the S&P’s velvet ropes shall come to a very sudden halt. Imagine the heartbreak if Saylor’s dreams collapsed due to the market equivalent of slipping on a banana peel. 🍌

The S&P, ever the aristocrat, admits only those whose past four quarters glisten with positive cumulative earnings. Strategy, having illuminated the fiscal landscape with a series of sizable quarterly losses, now pins its hopes on one bountiful second quarter, the kind only possible if one’s revenue is as unreasonably tied to Bitcoin as an Edwardian dandy to his monocle.

Further complicating this operetta, the ASU 2023-08 accounting rule (which, one imagines, exists mainly to keep auditors entertained on rainy Tuesday afternoons) now forces Strategy to adjust its books each quarter according to Bitcoin’s latest whim. A grand arrangement, really: nothing quite says “fiscal prudence” like letting your fortune rise and fall on the emotional state of Internet money. 🤑

For those keeping score, Strategy has stockpiled a frankly indecent 592,345 BTC—a hoard sufficient, perhaps, to alarm Fort Knox. Walton’s 91% forecast emerges from Bitcoin’s prior dances: since 2014, only 8.7% of observed periods saw Bitcoin tumble the requisite 10% in six days. These are odds roughly equivalent to attempting to catch a bus in rural Devonshire and actually succeeding.

Tick tock. The closer Q2’s end, the higher the chances for Saylor’s triumph. The daily barracks bulletin reads:

  • 5 days to go: 92.4% (domestic staff somewhat optimistic)
  • 4 days: 93.4% (champagne chilling quietly)
  • 3 days: 94.5% (hedge funds circling, hungry)
  • 2 days: 95.8% (Saylor rehearses acceptance speech, in Latin)
  • 1 day: 97.6% (Bitcoin threatens to join the House of Lords)

Alas, geopolitics loves to throw a spanner in the works: a recent rude scuffle between Iran and Israel briefly sent Bitcoin drooping below $100,000, evoking collective gasps from both investors and meme-makers. Luckily for our participants, order has since scrambled back, BTC now parading at $106,200—for the moment, Saylor’s destiny is back on track.

Should Strategy infiltrate the S&P, it will become merely the second of the crypto-rated rabble permitted entry in 2025, after the doughty foot soldiers at Coinbase blazed that particularly eccentric trail in May. One can only imagine the conversations at the next S&P committee luncheon: “Have you met our new members? They brought their own blockchain.” 🚀

In sum, it’s a tale as old as markets themselves: a chap, a coin, a dream… and just enough probability to keep us all hooked. Bring popcorn.

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2025-06-25 18:35