Strategy (MSTR) Becomes Wall Street’s Favorite Stock to Bet Against: A Masterclass in Sarcasm

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Ah, Strategy (MSTR)-the stock that’s taken up residence at the pinnacle of Wall Street’s “most-shortened” leaderboard, according to Goldman Sachs, who, I’m sure, is thrilled to share this little nugget of financial drama. It’s now the preferred vehicle for those who wish to bet against the glory of Bitcoin without having to go through the effort of, you know, understanding it. In fact, MSTR has become quite the lovely proxy for Bitcoin exposure-leverage and all. How quaint.

Wall Street’s Latest Obsession: The Short Trade on Strategy

In Goldman’s latest chart-topping game of ‘Which Stock Can We Bet Against Today?’, MSTR claims the top spot, with short interest occupying 14% of its market cap, leaving Charter Communications-bless its heart-at 12%. And the rest? CoreWeave and Coinbase are also in the running, with short interest hovering around 11%. A veritable race to the bottom, one might say. Then there’s the usual suspects: Western Digital, Dell, Palo Alto Networks, all at a meager 8%. Oh, how the mighty have fallen.

In case you’re wondering about the size of this circus, MSTR flaunts an equity cap of around $34 billion, with 53 hedge funds holding a rather charming 3% of it. Hedge funds were also thoughtful enough to maintain this position throughout 2025-how considerate of them. The stock, of course, has delivered a delightful (18)% return year-to-date. Truly, the gift that keeps on giving.

For comparison, let’s talk about Charter-lovely Charter-boasting a modest $30 billion equity cap and an army of 62 hedge funds holding it, also at around 3%. But with a more respectable 15% YTD return. That, my dear friends, is how you manage to keep your hedge fund portfolio just a little bit more charming.

CoreWeave, on the other hand, takes a different approach. A $39 billion equity cap, a hearty 62 hedge funds, and-oh yes-a whopping 27% hedge fund ownership as of 30-Sep-2025. The perfect balance between risk and reward, with a 33% YTD return to match. Absolutely delightful, darling.

Coinbase, despite its trendy charm, finds itself at $37 billion with 72 hedge funds owning it, yet its YTD return dances a somber (27)%. No one’s perfect, darling.

Ah, but hold your applause! Enter Tom Lee from Fundstrat, who has a rather endearing way of framing things. He believes that this heavy short interest is not a sign of impending doom but rather a deliciously crowded trade-one that’s priced in all the bad news. How poetic. “When a stock becomes a ‘consensus’ short,” he says, “it’s a crowded trade… hence, a stock can rise on ‘bad news’ because, well, it’s already priced in.” A true financial romantic.

Then we have Brian Brookshire, advisor to Moirai Capital, who points out the more subtle nuance of this whole charade. He suggests that much of the short interest is a cheeky MSTR/BTC basis trade, which may explain the mysterious allure. Jane Street, he claims, has recently acquired a rather conspicuous IBIT position. All bets, it seems, are off when the Bitcoin bull market makes its grand return. A spectacular thing, indeed.

Saylor’s Bold Message to the Bears: “Please, Short Us”

Strategy’s executive chairman, Michael Saylor, has never been one for subtlety. In fact, he’s practically dared the bears to short his stock. In a previous interview, he made his feelings clear: “If you really hate Bitcoin, I want you to love us,” he said, practically winking through the screen. “We’re the perfect instrument to short because I promise you, we won’t sell it. We’re going to be levered long Bitcoin. And if you don’t like it, or just want to hedge it, you can sell our stock, sell puts, or buy puts. It’s all very, very simple.” Oh, Michael, your confidence is truly captivating.

His point wasn’t merely that shorts are welcome-it’s that Strategy’s whole existence is one big, neon sign saying: “Come on, take a bet. You know you want to.” Consistency, transparency, and of course, that eternal promise: “We’ll buy Bitcoin and never sell it. We’ll borrow money intelligently.” Such sincerity.

For those who have a soft spot for Bitcoin-native investments, MSTR has now become a gloriously high-conviction battlefield. The longs treat it as a turbo-charged bet on Bitcoin, while the shorts view it as the purest way to bet against that very package. What a beautifully absurd game we’re playing.

At press time, MSTR is trading at $127.80. Get in while it’s hot, or not. It’s entirely up to you, darling.

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2026-02-25 21:04