Economist Peter Schiff isn't known for his Bitcoin optimism, and Wednesday brought another dose of his trademark bearishness. This time, he's taking aim at both Bitcoin and Strategy Inc. (MSTR), the company that's essentially become a leveraged bet on cryptocurrency.

A Grim Forecast for Strategy and Bitcoin

Schiff took to X to share his bleak predictions, suggesting Strategy's stock could get cut in half from its current $160 price point. "It's hard to find a chart that looks worse than Strategy's MSTR," Schiff wrote. "At a minimum, the stock should drop to about $80, which is half its current price."

But the bearish forecast doesn't stop there. Schiff also set $50,000 as Bitcoin's "minimum target," noting that MSTR's anticipated plunge won't happen unless the cryptocurrency itself takes a major hit first. For context, Bitcoin last traded at those levels back in February 2024.

The Strategy Question

Schiff has been a persistent critic of Strategy's investment approach, particularly questioning the logic behind the company's relentless Bitcoin accumulation. His core criticism: Why keep buying Bitcoin when the company's shares are valued at less than the actual BTC holdings?

According to TradingView, momentum-based technical indicators and moving averages currently flash a "Sell" signal for MSTR stock. Strategy didn't immediately respond to requests for comment on Schiff's predictions.

Michael Saylor's Bitcoin Bet Faces Headwinds

Here's where things get interesting. Strategy, widely viewed as a proxy for Bitcoin exposure with leverage, has been struggling lately. The company's market value stands at $49.01 billion, which has now dipped below the value of its Bitcoin holdings at $58.17 billion. That's an unusual situation that raises questions about market confidence in the business model.

The numbers tell a stark story: MSTR shares have plunged 57% over the past six months, dramatically outpacing Bitcoin's 17% decline during the same period. That gap suggests investors are worried about more than just cryptocurrency prices.

Earlier this month, the company announced a $1.44 billion reserve designed to fund dividends and interest payments without having to sell Bitcoin during market downturns. Executive Chairman Michael Saylor has stated that the firm could sell its Bitcoin holdings if it's in the "best interest of shareholders," though that seems to contradict the company's aggressive accumulation strategy.

And aggressive it remains. This week alone, Strategy reported purchasing 10,645 BTC for $980.3 million, pushing its total holdings to 671,268 BTC. The company appears undeterred by market turbulence or mounting criticism.

At the time of writing, Bitcoin was trading at $86,205.44, down 1.26% over the past 24 hours. Meanwhile, Strategy shares rose 0.10% in after-hours trading to $160.54, after closing 4.25% lower at $160.38 during Wednesday's regular session.

The stock currently shows a weaker price trend across short, medium, and long-term timeframes, raising questions about whether Schiff's dire predictions might have some merit after all.