How Strategy’s $14B Bitcoin Windfall Made Even Wilde Raise an Eyebrow

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After scooping up 2.8% of Bitcoin’s total supply like a gourmand at a dessert buffet, Strategy has finally set down its fork for a moment of dainty indigestion, declaring not a single BTC was nibbled for the first time in three months. One wonders if it’s remorse or simply the ennui of excess, but a $14 billion unrealized gain in Q2 suggests that, even in their boredom, they keep tripping over piles of digital gold.

Per a Form 8-K filed with the ever-watchful U.S. Securities and Exchange Commission on July 7 (a body famed for its love of forms and utter lack of Bitcoin), Strategy indulged in zero-market gluttony between June 30 and July 6. Yes, readers, the mighty accumulator of Tysons Corner, Virginia decided to play coy for an entire week, as if in silent protest against the tyranny of abundance.

What drove this sudden steely self-restraint? Consider: $14.05 billion in Q2 gain, a mere trifle of a $4.04 billion tax expense lurking awkwardly in the corner, and 597,325 BTC held tightly—worth $64.4 billion if you believe in numbers, or the tooth fairy. Even after such a Bacchanalian binge, Strategy’s portfolio boasts a $22 billion “paper profit” on a wild $42.4 billion investment. My, my, what’s a little deferred tax between fabulously speculative friends? 💸

Strategy’s Bitcoin Pause: Brilliant Gambit or Digital Fatigue? 🎭

The sudden cessation of Strategy’s epic crypto feast has the hoi polloi in a tizzy. Surely, the company—with Michael Saylor crowing “some weeks you just need to HODL” on social media—must know something the rest of us do not. Or perhaps, dear reader, even financial titans require a breather after a spree. It is, after all, easier to count coins when one stops chasing them.

Some weeks you just need to HODL.

— Michael Saylor (@saylor) July 6, 2025

The $14 billion Q2 windfall is less a stroke of luck and more a cunning coup de grâce, though this pause reeks less of panic than of a gentleman pausing mid-waltz for a sip of champagne—and possibly a consult with his tax accountant.

Unexamined, the Form 8-K would seem to show mere laziness. But consider: the last purchase—4,980 BTC for a delectable $531.9 million at $106,801 a slice—occurred June 29, after which Strategy simply loitered in the ballroom as the price wafted between $105,000 and $110,000. “Why chase?” they seem to say. “We have enough for now. Let others scramble for the crumbs.”

Such restraint might be less about conviction and more about tax headaches. The pesky $4.04 billion deferred tax expense sits glowering in the foyer, reminding Strategy that, while paper gains are delicious, taxes remain stubbornly real—more so, alas, than internet money.

Of course, Strategy’s binge has been financed with the deft flick of a Victorian banker’s wrist: stock sales and select debt concoctions. In Q2, $6.8 billion was conjured from at-the-market offerings of Class A common ($MSTR) and a trio of preferred shares—STRK, STRF, STRD—all named with the whimsical brevity of someone avoiding vowels.

Such instruments, yielding 8% to 10%, are irresistible to the yield-hungry, but even Wilde would snigger at the risk (and secretly wish he’d thought of it first). The audacious “42/42” plan sets an $84 billion fundraising target by 2027, presumably by distracting investors with shiny objects while quietly printing more shares and convertible notes.

To date, this parade has dazzled the audience, but should Bitcoin’s price swoon or investor appetite curdle, one imagines the champagne will run dry rather quickly. For now, though, let’s toast to their audacity—and pray they don’t develop a taste for Ethereum next. 🥂

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2025-07-07 16:52