Short Seller Bets Against Saylor to Buy MORE Bitcoin?!

A legendary short seller just made a bold bet… against Michael Saylor and his multi-billion-dollar Bitcoin play. But here’s the twist — he’s using that to buy even more Bitcoin. Wait, what?! Is this the ultimate arbitrage or just another big risk in a market built on hype? Stick around, this might be the most important trade you hear about this month…

Jim Chanos, the guy who took down Enron back in the day, is back in the spotlight. But this time, his target is none other than Michael Saylor’s MicroStrategy, or as Chanos calls it… “Strategy.”

So what’s happening?

MicroStrategy stock — now trading around $1,500 per share as of mid-May 2025 — is riding high again, driven largely by the $59 billion worth of Bitcoin it holds. But Chanos isn’t impressed. He’s shorting the stock… and using those returns to buy actual Bitcoin.

“We’re just doing what Saylor’s doing,” Chanos said, “only smarter.”

Let’s unpack that.

Chanos is executing a relative value trade, shorting MicroStrategy stock while going long on BTC. It’s a sophisticated arbitrage bet that the premium MSTR trades at compared to the Bitcoin it holds will eventually shrink.

Why does this matter?

At its peak in 2020, MicroStrategy’s stock was priced at 6x the value of its Bitcoin holdings. Today, that multiple still floats around 2.5x to 3x. And to Chanos — that’s pure speculation, not fundamentals.

He’s not alone in noticing the hype.

Over 130 public companies have copied MicroStrategy’s “buy Bitcoin to boost stock” strategy. Just last week, a healthcare company merged with a Bitcoin-holding firm, trying to raise $700 million to… you guessed it… buy more Bitcoin.

This is starting to feel a little like the dot-com bubble, just with laser eyes.

This isn’t the first time markets have seen this kind of split between narrative-driven stocks and underlying asset value. Back in 2000, dot-com companies were trading at 10–20x future revenue projections. No profits, just dreams.

Today, the dream is Bitcoin on balance sheets.

Now, I’m not against it. In fact, I’ve been bullish on BTC since 2015. But let’s be real — owning Bitcoin directly is not the same as buying into a company that owns Bitcoin.

And that’s the heart of Chanos’s bet — retail investors are paying a premium for a structure they could replicate just by holding Bitcoin directly.

Here’s my take:

If Bitcoin climbs past $100K this year — which, by the way, is not off the table with current ETF flows and the post-halving cycle — MicroStrategy might continue to pump. But if BTC stagnates or drops, the stock premium could collapse fast.

Question to viewers:

“Do you think Chanos is right — will MicroStrategy’s stock premium fade? Or is Saylor playing 4D chess with corporate balance sheets?”

Drop your thoughts in the comments. And don’t forget — the real alpha isn’t just following the hype… it’s understanding why the market moves.

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