Strategy Risks Selling $4 Billion In Bitcoin, MSTR Stock To Get STRC Back To $100 Par

Arca Chief Investment Officer Jeff Dorman believes that Strategy (NASDAQ: MSTR) may be forced to sell billions of dollars worth of Bitcoin or common stock to ease concerns about its STRC preferred stock.

Dorman Warns Strategy May Have To Sell More Bitcoin, MSTR Stock

The comments followed Strategy’s STRC preferred stock trading down to as low as $82.53 on June 18. Thereafter, it rebounded a bit but still closed at $88.59, which is far short of its $100 par value. Peter Schiff even warned of a lawsuit against Michael Saylor’s Strategy as STRC is continuing decline.

In a post on X, Dorman declared that the “MSTR pickle continues.” He noted that management will have to take a hard decision because of mounting pressures on its capital structure.

“Either sell an enormous amount of BTC and MSTR to help bring STRC back up near par,” he wrote. If not, it would have to continue to “watch every part of your cap structure melt because of the uncertainty [they’ve] created,” he added. His comments coincide with criticism over the recent 32 BTC sale.

Dorman said his base case, which he gave a 70% chance of occurring, is that Strategy will follow its existing strategy of selling “small amounts of MSTR every month at non-accretive levels.” If that is the case, he said, “at least a glimmer of hope,” for STRC holders while Bitcoin is pretty much intact, “MSTR would get hammered.”

He assigned a 25% probability to what he referred to as the “right thing,” which is Strategy selling between $3 billion and $4 billion worth of Bitcoin. Moreover, Dorman said such a step would “buy a ton of time” be “good for STRC” and only “bad for BTC short-term but good long-term.”

Preferred Dividends Remain A Key Obstacle

Dorman had set aside 5% for what he referred to as the “nuclear option.” It’ll come in handy to do away with payments on preferred securities that are contingent on the dividend, he added.

MSTR pickle continues: What I laid out 2 weeks ago is still the only viable path to save $BTC and $MSTR in the short-run.

Either sell an enormous amount of BTC and MSTR to help bring $STRC back up near par, and at least buy yourself some time, or continue to watch every part… https://t.co/JAztCieaZ1

— Jeff Dorman (@jdorman81) June 18, 2026

The move may result in a “30-40 cents on the dollar” for preferred shares, and would likely “close the capital markets” to Strategy, he said. It would, however, also solve a “$1.7 bn per year cash outlay problem.” Dorman said.

The Arca executive also questioned Strategy’s valuation. He said that the MSTR stock is “still trading at 1.15 mNAV using the correct calculation.” He calculated that the company has approximately $35.2 billion worth of unencumbered Bitcoin collateral and $40.4 billion worth of equity market capitalization.

Due to this, Dorman said MSTR is “still going a lot lower” and “should trade at a discount to NAV now.”

He said if Bitcoin makes a quick turnaround and goes higher, then MSTR stock could see an upside. However, he warned that it centers on a big assumption that Strategy doesn’t dilute itself more from dividends or asset sales or future fundraising.