Bitcoin Bonanza: Strategy’s $50M Bet on Crypto & the Wall Street Drama Unfolds

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Markets

What to know:

  • Strategy purchased 487 bitcoin for a cool $49.9 million-peanuts, right?
  • For the first time, Strategy employed the magical short-duration, high-yield Stretch (STRC) preferred series at-the-market offering to fund this acquisition. Sounds fancy, doesn’t it?
  • Despite the stock’s dramatic fall, the company dares to hope that the bottom is finally here. The agony might be over… or maybe not.

Ah, Strategy (MSTR), the grand corporate champion of bitcoin, announced on Monday that it splashed a staggering $49.9 million on bitcoin just last week. The result? An impressive 641,692 bitcoins stashed away, worth an eye-watering $68 billion at today’s dizzying prices.

Of course, this was just another drop in the ocean for the company, which has been buying up bitcoin in such tiny little bites that one might wonder if they’re really going for world domination or just trying to keep their heads above water. Their capital-raising efforts? Well, let’s just say they’re a little, shall we say, constrained-mostly thanks to the recent nose-dive of MSTR’s common stock. Ouch.

But wait-this latest bitcoin binge is actually worth noting. Why? Because for the first time ever, Strategy dipped its toes into the magical waters of the at-the-market program with its Stretch (STRC) series of preferred stock. They raised a respectable $26.2 million. And for those who enjoy a little drama, Strategy’s newly boosted STRC annual dividend rate now stands at a hefty 10.5%, paid monthly. A sweet deal for anyone still brave enough to be on this rollercoaster.

And the rest of the funds? They came courtesy of the ever-grumpy STRF “Strife” preferred shares. Because, why not?

Green shoots?

Now, let’s talk about the elephant in the room: while bitcoin’s value has plummeted, Strategy’s stock has taken an even more painful dive. It’s been like watching a slow-motion train wreck. Investors, once willing to pay a premium for Strategy’s bitcoin holdings, have since bailed out like rats from a sinking ship. The premium? Poof! Gone.

One man, Jim Chanos (a short-seller extraordinaire), made a public spectacle of calling out the premium. In fact, he went so far as to sell MSTR short while simultaneously holding a long position in BTC. But, surprise! Over the weekend, Chanos admitted that his trade-one that was as successful as a Netflix binge-watch-was finally coming to an end. A moment of clarity, perhaps? Or just a well-timed exit?

Contrarians, however, are probably popping open champagne after reading a recent WSJ article. For the first time, the editorial team-yes, the very same team that usually writes about the Kardashians-has caught wind of the months-long collapse in the prices of digital asset treasury companies. Big shocker, huh?

One trader, who must’ve been a real character at parties, had this to say: “The whole concept makes no sense to me. You’re just paying $2 for a $1 bill… Eventually, those premiums will compress.” Well, newsflash: they already have, buddy. Welcome to reality.

As for MSTR shares? They’ve eked out a modest 3.2% gain in premarket trading, just as bitcoin made a surprise rally to climb back above $106,000. Funny how that works, isn’t it?

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2025-11-10 17:35