Strategy faces stress test as Grayscale warns leveraged Bitcoin model may force further sales

Strategy, the company formerly known as MicroStrategy, sold 32 Bitcoin on June 1 for roughly $2.5 million. That’s pocket change for a firm sitting on approximately 840,000 BTC worth around $55 billion. But Grayscale’s research team thinks this small transaction tells a much bigger story.

The sale was made to cover costs tied to Strategy’s STRC preferred equity instrument, and Grayscale’s head of research, Zach Pandl, says it signals that the company’s leveraged Bitcoin accumulation model is under meaningful stress.

The math problem behind the headlines

The company’s STRC preferred shares carry dividend obligations that require real cash. Those shares were designed to trade around $100 but are currently sitting near $95, which makes the financing economics progressively worse.

Meanwhile, Strategy’s average acquisition cost for its Bitcoin sits at an estimated $75,500 to $76,000 per coin. With Bitcoin trading in the $62,000 to $63,000 range, that puts the company’s unrealized losses somewhere around $11 billion to $12 billion.

Pandl argued that this dynamic limits Strategy’s ability to keep buying Bitcoin at current share prices.

“The shift in approach from one of the world’s largest BTC holders has weighed on market sentiment,” said Pandl.

Why a 32 BTC sale matters more than it should

The sale reveals that Strategy’s cash flow situation is tight enough that it can’t simply absorb preferred equity costs from operating revenue. Instead, it’s tapping its Bitcoin treasury, however modestly, to meet obligations. That’s a qualitative shift from “we buy Bitcoin and never sell” to “we sell Bitcoin when we have to.”

If Bitcoin prices remain below Strategy’s average cost basis, the pressure on its preferred equity only intensifies. More dividend payments come due. STRC continues trading at a discount. And the path of least resistance becomes selling more Bitcoin to cover the gap.

Grayscale’s silver lining argument

“Less Bitcoin on levered DAT balance sheets and more on diversified corporate balance sheets will be a positive,” Pandl said.

Grayscale’s research also pointed to reduced ETF flows and broader market volatility as compounding factors.

What this means for investors

For Bitcoin investors more broadly, the key variable to watch is whether Strategy’s selling stays at the token-level, covering small obligations with small sales, or escalates into something more significant. An 840,000 BTC position unwinding in any meaningful way would be a seismic event for a market that, despite its growth, still lacks the depth to absorb massive concentrated selling without price dislocations.

The STRC preferred share price is arguably the best real-time indicator of this risk. If it drifts further below its $100 target, the cash flow pressure on Strategy intensifies. If it recovers toward par, the urgency to sell Bitcoin diminishes.

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