Strategy Is Now Worth Less Than Its Own Bitcoin: Is Saylor about to be forced to sell?

For years, the simplest way to bet on Bitcoin (CRYPTO:BTC) without buying it yourself was to buy Strategy. Michael Saylor turned his company into a giant Bitcoin holding machine, and for most of that run, the market paid far more for the stock than the Bitcoin behind it was worth.

However, that narrative has now changed. Strategy (NASDAQ:MSTR | MSTR Price Prediction) trades below the value of the Bitcoin in its own treasury—the MSTR stock has fallen about 79% from its July 2025 high of $457—and the company that built its whole identity on never selling has quietly started selling.

That leaves the largest corporate Bitcoin holder facing one headache: Will Saylor be forced to sell even more Bitcoin?

How Strategy Ended Up Worth Less Than the Bitcoin It Holds

It sounds impossible for a company to be worth less than the assets in its own treasury, but that’s where Strategy has ended up. It holds about 847,000 Bitcoin worth roughly $51 billion right now, while the entire company is worth about $31 billion.

Back in late 2024, the market paid about 3.4 times the value of Strategy’s Bitcoin to own the stock, which was a steep premium for getting Bitcoin exposure in a single share. That premium powered the whole model, and it has been thinning ever since. By late 2025 it was down to about 1.2 times, and today it has essentially disappeared.

The collapse is also why the stock has fallen so much more than Bitcoin itself. Over the past year Bitcoin is down about 51%, while Strategy’s stock has dropped 78%. The premium worked like leverage on the way up, multiplying Bitcoin’s gains into bigger gains for the stock. Now it runs in reverse, so as the premium shrinks it drags the stock down faster than Bitcoin is falling.

Strategy’s own dashboard still shows a figure called mNAV just above 1, which looks like it contradicts all of this. The difference is the debt and preferred shares that rank ahead of the common stock. 

Lenders and preferred holders have first claim on about 41% of the Bitcoin, so once you set their share aside, what’s left for common shareholders is worth roughly what the stock trades at today, or a little less. However you measure it, the premium Saylor minted billions from is no longer there.

Why Strategy Can’t Buy Bitcoin the Way It Used To

While the MSTR stock traded above the value of its Bitcoin, Strategy could sell new shares at that premium, use the cash to buy more Bitcoin, and end up with more Bitcoin behind every share than before. Existing holders came out ahead even as new shares were issued, so the company could turn around and do it again the next week—and the whole machine ran on that premium.

Over the past year, most of that buying ran through a preferred share called STRC, basically a high-yield IOU it sells to raise cash. STRC funded more than half of the company’s Bitcoin purchases in 2026. It only works as a funding tool while it trades near its $100 face value, because that’s the level that lets Strategy keep issuing more of it.

Both of those conditions have now broken. With the stock trading below the value of its Bitcoin, selling new shares to buy coins would shrink each holder’s Bitcoin per share instead of growing it. STRC has also dropped well below par, falling as low as $74 as of late June, or 26% under its $100 face value. So, selling a $100 promise for $74 is an expensive way to raise money.

Moreover, Strategy’s own filings show the machine stalling. In the week ending June 21, it raised nothing at all from its preferred shares and sold only about $336 million of common stock. At its peak the company was pulling in well over a hundred million dollars a day, so the engine has slowed to a fraction of what it was, with its main fuel line shut off entirely.

The $1.7 Billion Reason Strategy Is Now Selling Bitcoin

All those preferred shares Strategy sold to buy Bitcoin came with a catch: they pay out cash dividends every year, forever. That bill now runs to about $1.7 billion a year, and it doesn’t care what Bitcoin does—and it also grew fast. At the start of 2026 it was only a few hundred million, but months of selling more and more preferred shares pushed it to where it is now.

For a while none of this was a problem, because the same machine that bought Bitcoin also covered the dividends. Strategy keeps a cash reserve for exactly this, and right now it holds about $1.4 billion, or roughly ten months of dividend payments. That sounds comfortable until you remember the machine that refills it has stalled.

So in late May, Strategy did something it had not done since 2022: it sold Bitcoin. The amount was tiny, just 32 coins for about $2.5 million, but the reason behind it mattered far more than the size. Strategy stated plainly in an SEC filing that it expected to use the proceeds from its Bitcoin sales to fund the dividends on its preferred shares.

Thirty-two coins out of 847,000 is almost nothing, as it’s about four-thousandths of a percent of the pile. But selling any at all signals something, because for years Saylor’s whole pitch was that Strategy would never sell Bitcoin. That promise has quietly softened to never being a net seller, which is a very different thing once the dividends come due in cash twice a month. For now, those sales are deliberate and small, and the question is whether they stay that way.

Is Saylor About to Be Forced to Sell?

This is where the words “forced” and “death spiral” get thrown around a lot. The fear is that if Bitcoin keeps falling and Strategy keeps selling coins to pay its bills, each sale pushes the price lower, which forces more selling, until the whole structure caves in. It’s a scary picture, but it falls apart the moment someone actually models the worst case.

What a Three-Year Stress Test Actually Found

One analyst did exactly that. Adam Livingston, who is bullish on Strategy, built a deliberately harsh three-year model and dared it to break the company. He assumed Bitcoin crashes to around $26,600, the stock falls below half the value of its Bitcoin, capital markets slam shut, and Strategy is forced to sell coins to cover its obligations. In other words, everything goes wrong for the company.

Even in that scenario, Strategy still doesn’t go bankrupt. The model has it selling around 115,000 Bitcoin over three years to keep paying its bills, which is serious damage, yet it still ends the stretch holding more than 731,000 coins and recovering as Bitcoin stabilizes. That holds up because Strategy has survived a similar squeeze before.

Looking back to the bottom of the 2022 bear market, Strategy held about 130,000 Bitcoin and owed more against them than they were worth, leaving common shareholders with negative Bitcoin exposure. Even then, with a far weaker balance sheet than it has today, the stock never fell below $10.

The Bigger Risk Is the Shrinking Bitcoin Per Share

So if bankruptcy isn’t the danger, what is? It’s the slow erosion of how much Bitcoin each Strategy share actually represents. In that same worst-case model, the Bitcoin backing each share falls by about 94%, from 138,161 satoshis to under 8,000. The company would still be alive, but a share bought for its Bitcoin exposure would own a fraction of what it used to.

That doesn’t mean Strategy is collapsing today, as it’s still buying Bitcoin, just barely. In its most recent week it bought only about 520 coins, a fraction of its old pace, and put most of its stock-sale cash into the reserve instead. Its debt is mostly long-dated and doesn’t come due for years; the earliest its lenders can ask for their money back is late 2027. The pressure is the cash dividend, not a loan about to be called.

For Strategy to fund itself the easy way again, the stock needs to climb back above roughly $183, which lines up with a Bitcoin price near $91,500. If it gets back above that level, the premium returns and the buying loop restarts. If it stays below, Strategy keeps grinding through this slow bleed, selling a little here and there while its Bitcoin per share shrinks. That’s the honest answer to whether Saylor is forced to sell. It’s not a dramatic collapse, but a slow squeeze that gets tighter the longer Bitcoin stays down.

What Saylor Selling Bitcoin Would Mean for the Rest of the Market

Saylor is not about to be forced into a fire sale just yet, but the change is still crucial far beyond Strategy. For years the company was the most reliable buyer in the Bitcoin market, soaking up coins on every dip. But the buyer has gone quiet and even turned into a small seller, right as spot Bitcoin ETFs bleed money in their longest losing streak since they launched in early 2024. The bigger worry, as Grayscale’s Zach Pandl has pointed out, is that the market now needs other buyers to absorb what Strategy can no longer take in.

Saylor’s own read is that this is just capital rotating into the AI boom, not a crack in Bitcoin, and he may turn out to be right. For Bitcoin and MSTR alike, three things are now vital: the premium climbing back above 1, STRC reclaiming its $100 face value, and Bitcoin pushing back toward $91,500. The BTC price is the one that turns Strategy from a nervous seller back into the buyer the market got used to.