Key Highlights
- Peter Schiff warned that Michael Saylor may eventually need to sell some of Strategy’s Bitcoin if MSTR stock keeps falling.
- CryptoQuant urged Strategy to slow or pause Bitcoin purchases and focus on rebuilding cash reserves as financial pressure grows.
- Strategy’s stock and preferred shares have fallen sharply, while dividend obligations have risen from $300 million to $1.2 billion in six months.
Strategy’s Executive Chairman Michael Saylor’s famous “buy and hold forever” Bitcoin strategy is facing renewed scrutiny as Strategy’s stock fell by 5% today.
The warning came from economist and longtime Bitcoin critic Peter Schiff, who said in a post on X on Wednesday that Saylor could eventually be forced to sell some of Strategy’s Bitcoin if the company’s stock continues to slide.
Schiff’s comments came as Strategy’s common stock, MSTR, dropped to $103 on Tuesday, its lowest level in nearly two years and down 81% from its all-time high.
Gap between MSTR and Bitcoin is growing
Schiff believes the main issue is the growing gap between Strategy’s stock market value and the value of the Bitcoin it owns. Strategy is currently the largest corporate holder of Bitcoin, with 847,363 BTC worth about $53 billion at current market prices. However, the company’s shares have been falling faster than the value of its Bitcoin holdings.
According to Schiff, if that gap continues to widen, Strategy may eventually be pushed into selling some Bitcoin and using the money to buy back its own stock. In simple terms, buying back shares could reduce the number of shares in the market and help close the gap between the company’s stock price and the value of its assets.
Still, Schiff argued that such a move could create another problem. Because Strategy owns such a large amount of Bitcoin, a major sale could put pressure on the market and push Bitcoin’s price lower.
“That would reduce the discount, but it may not raise the share price, as Bitcoin will crash,” Schiff wrote. “That’s the box Saylor put himself in.”
CryptoQuant urges Strategy to protect its cash
While Schiff focused on the risks of Strategy’s Bitcoin-heavy approach, crypto analytics firm CryptoQuant raised concerns about the company’s financial flexibility. CryptoQuant CEO Ki Young Ju, in a recently published report, said Strategy may need to slow down or temporarily stop buying more Bitcoin and focus instead on strengthening its cash reserves.
“Strategy’s BTC buying here looks more like a liquidity sink than a price catalyst,” Young Ju said.
According to CryptoQuant, Strategy’s cash reserves have fallen by about 38% since the beginning of 2026. The firm said the company has continued spending money on Bitcoin purchases while also dealing with debt obligations and dividend payments linked to its growing capital structure.
Rising dividend costs add more pressure
Julio Moreno, CryptoQuant’s head of research, said a $1.5 billion repurchase of convertible notes due in 2029 has added pressure to the company’s finances. He also noted that Strategy’s yearly dividend obligations have increased from about $300 million to $1.2 billion in just six months.
“Dividend coverage collapsed from 7+ years to just 14 months. The company needs to stop buying Bitcoin and rebuild cash.” CryptoQuant warned on X.
Moreno estimated that Strategy would need around $2.8 billion in cash over the next two years to improve dividend coverage and restore confidence among investors. However, he argued that selling Bitcoin now may not be the best solution because it could lock in unrealized losses estimated at $10.6 billion and reduce shareholder value.
Instead, Moreno suggested that Strategy could support its finances through dividend adjustments and additional MSTR share offerings.
Strategy stays committed to Bitcoin
Meanwhile, between May 26 and May 31, Strategy sold 32 BTC for $2.5 million, marking its first Bitcoin sale. Saylor later said the transaction did not change the company’s long-term commitment to Bitcoin. Earlier this week, the company sold $335.5 million worth of MSTR shares and used the proceeds to buy another 520 BTC at an average price of $67,068.
For now, Strategy remains committed to its Bitcoin-focused approach. However, with its stock under pressure and dividend obligations growing, questions are emerging about how long the company can continue expanding its Bitcoin holdings at the current pace.
Also Read: When Will Bitcoin Price Reach New High? Here’s What An Analyst Predicts
