Saylor’s $9 Billion “Diamond Hands” Test: Strategy Defies Shorts with 100th Bitcoin Buy
In corporate finance, there's betting big and then there's Michael Saylor - the man with absolute conviction. With February 25, 2026...
Quick overview
- Michael Saylor's company, Strategy, recently acquired its 100th Bitcoin, bringing its total holdings to 717,722 Bitcoins, approximately 3.4% of the total supply.
- Despite facing significant losses and being the most shorted large-cap U.S. stock, Saylor remains committed to a long-term 'Buy and Hold' strategy.
- While institutional investors are pulling back from Bitcoin ETFs, some, like Anchorage Digital, continue to support Saylor's vision by investing in Strategy's preferred stock.
- The market is divided, with 'Strategic HODLers' viewing current prices as a buying opportunity, while ETF managers are reducing risk amid economic uncertainties.
In corporate finance, there’s betting big and then there’s Michael Saylor – the man with absolute conviction. With February 25, 2026 marking the day Strategy, his company, nailed its 100th Bitcoin acquisition.
Despite the fact that at $65,500 a pop, Bitcoin’s having a bit of a rough time and’s leaving Strategy with a not-insignificant $8.2 – $10 billion loss just waiting to happen, Saylor’s doubling down.
While hedge funds are piling into the “bet against Strategy” trade, the firm’s actually moving money between accounts left and right – which tells you in no uncertain terms their “Buy and Hold onto forever” machine is showing no signs of slowing down.
The 100th Buy: Strategy vs. The Market
Meanwhile, the rest of the market is sitting pretty tight, with everyone else playing it safe and waiting for a better day to invest. Strategy just went out and bought another 592 Bitcoins for $39.8 million, that’s not a typo, 39.8 million, so it’s now holding a crazy 717,722 – that’s roughly 3.4% of the total 21 million supply of BTC.
- The Portfolio:4% of the world’s Bitcoins? Yeah, that sounds right, to the rest of the market, but to Saylor and his crew, Strategy is the undisputed king of corporate treasuries – they’ve got more Bitcoins than MARA Holdings (53,250) and even Tesla (11,509).
- The Real Cost: With an average price of about $76,000 a Bitcoin – yeah, you can say they’re “underwater,” but then again, Saylor’s already said he can ride out a drop all the way down to $8,000 (understandably, people think he’s lost it).
After 2 months of silence, #Strategy's wallets are active again.
They moved 1,300 $BTC($83M) to new wallets, likely just reorganizing funds.https://t.co/FgZG2ZWlVi pic.twitter.com/RR36JnI55e
— Lookonchain (@lookonchain) February 25, 2026
The “Short Interest” Crown: Goldman Sachs Issues Warning
Strategy’s whole “all in” approach has made it the number one most shorted large-cap U.S. stock, according to Goldman Sachs. Institutional investors are taking a bet: if Bitcoin can’t make it back to $70,000, then Strategy’s gonna get slammed.
However, there are those who are supporting Saylor like Anchorage Digital – they just bought a ton of Strategy’s perpetual preferred stock (STRC), which tells you that some people really think the man’s long-term vision is gonna pan out.
ETF Exodus: Why Institutional Investors are Trimming
It’s funny, though, because while corporate investors like Saylor are aiming for the moon, the guys who manage “exchange traded funds” (ETFs) are quietly getting out. U.S. spot Bitcoin ETFs have been seeing outflow for 5 weeks in a row.
- The Brevan Howard Exit: The massive macro fund reduced its ETF exposure by over 17,000 BTC in the final quarter of last year, a move that set the tone for the current “sell-the-bounce” sentiment.
- BlackRock’s IBIT Under Pressure: Even the industry-leading iShares Bitcoin Trust (IBIT) has seen outflows totaling roughly $368 million this week alone.
- Cumulative Bleed: Since the start of 2026, roughly $4.5 billion has exited the Bitcoin ETF complex, as investors rotate capital into safer “cash” positions amid global tariff uncertainties.
Technical Snapshot: The “Short Squeeze” Potential?
From an analyst’s perspective, the high short interest in Strategy creates a “coiled spring” effect.
| Level | Strategy (MSTR) / BTC | Market Sentiment |
| Resistance | $71,000 (BTC) | Breaking this would trigger a massive “short squeeze” for MSTR. |
| Pivot | $64,000 (BTC) | The current line in the sand for ETF stability. |
| Support | $58,000 (BTC) | A break below could force “margin call” fears in the stock market. |
The Analyst’s Verdict: A Bifurcated Market
The market is currently split into two camps. On one side, you have the “Strategic HODLers” like Saylor, who view the current $65,000 range as a generational buying opportunity. On the other hand, ETF allocators are trimming risk amid macroeconomic headwinds.
For Professionals: The $66,400 level is gonna be a big deciding factor. If it holds, expect the “shorts” to get really nervous and a pretty massive crypto recovery to follow. Strategy is basically a leveraged Bitcoin investment – if you think that in say 5 years’ time, you’ll be getting $150,000 per Bitcoin, then this whole “underwater” situation is just small-time stuff.
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