Strategy Stock Hits $137 as Schiff Warns of 'Death Spiral', Saylor Posts Bull Video

Peter Schiff has once again issued his "death spiral" warning on Strategy (MSTR), even as the stock climbed to $137.40 amid a wider Bitcoin (BTC) rally. Michael Saylor responded by posting an AI-generated video of himself on a bull in Spain.

Since early August, Strategy's stock has risen sharply, mirroring a Bitcoin recovery that pushed the cryptocurrency above $80,000 this week. Schiff said the Thursday increase was mostly due to short sellers covering their positions, not real buying interest.

Schiff Stands Firm on His Bearish Outlook

A persistent Bitcoin critic, Schiff has for months contended that Strategy's preferred stock dividend commitments make the company vulnerable if Bitcoin declines again. He attributed Thursday's rally to a short squeeze, not renewed confidence in the stock.

Not sure what’s behind today’s sharp $MSTR rally, though I suspect short-covering has a lot to do with it. Nonetheless, I stand by my “death spiral” thesis, even if Strategy’s life expectancy has been extended a bit by the temporary Bitcoin rally.

Not sure what's behind today's sharp $MSTR rally, though I suspect short-covering has a lot to do with it. Nonetheless, I stand by my "death spiral" thesis, even if Strategy's life expectancy has been extended a bit by the temporary Bitcoin rally.

— Peter Schiff (@PeterSchiff) August 27, 2026

Schiff has previously described MSTR as a scam and warned of a death spiral linked to the same preferred stock structure, which carries a variable dividend that Strategy partly finances by issuing new shares.

Saylor Responds with Swagger

The executive chairman of Strategy posted a brief AI-generated video showing himself on a bull, with a simple caption.

Ride the ₿ull.

Ride the ₿ull. pic.twitter.com/NQpGefFkAO

— Michael Saylor (@saylor) August 27, 2026

Saylor posted the video on X. The clip appeared on the same day that Strategy's stock rally coincided with diminishing concerns that the company would have to sell Bitcoin to meet its obligations.

The contrasting responses highlight the disagreement over Strategy's business model. Schiff continues to see the same balance sheet risk he has pointed out for more than a year. Saylor, relying on Bitcoin's upward momentum, appears content to display his confidence publicly.

How well Schiff's warning holds up this time may depend on the duration of Bitcoin's rally.