Strategy Buys Bitcoin's Dip as Saylor Declares "Crypto Winter"

Strategy Inc. dropped another $168.4 million on Bitcoin last week while its executive chairman told the world we're in a crypto winter. That's the short version. The longer version involves a reversal on a bold prediction, an unrealized loss north of $5 billion, and a company that says it can ride this out even if BTC hits $8,000.

What Did Strategy Actually Buy?

Between February 9 and 16, Strategy scooped up 2,486 BTC at an average price of $67,710 per coin, according to an SEC Form 8-K filed on February 17. The firm funded the purchase by selling 660,000 shares of its Class A common stock (MSTR) for $90.5 million and 785,354 shares of its Stretch preferred stock (STRC) for $78.4 million.

This was Strategy's 99th Bitcoin purchase since it started stacking in 2020. Its total stash now stands at 717,131 BTC, purchased for a combined cost of roughly $54.52 billion. That's over 3.4% of Bitcoin's entire 21 million supply cap, locked up in one company's treasury.

Here's the notable part: this purchase actually lowered Strategy's average cost basis by $29, bringing it down to $76,027 per BTC. That's the first time the average dropped in nearly two and a half years, since September 2023. When you're sitting on 717,000 coins and your new buy is still meaningfully below your average, the math speaks for itself.

At Bitcoin's current price of around $67,800, that entire position is underwater. The unrealized loss totals approximately $5.7 billion, or roughly 10.5%. MSTR stock has been hammered too, falling about 63% from its highs after Bitcoin peaked near $126,000 in October 2025.

Didn't Saylor Say Winter Would Never Return?

He did. Back in June 2025, Saylor told Bloomberg that crypto winter was "not coming back" and that Bitcoin was headed to $1 million. Eight months later, he's singing a different tune.

In a Fox Business appearance on February 17, Saylor was blunt. "We are in a crypto winter," he said. "This is the fifth major drawdown of Bitcoin in the five years since I've been in the marketplace."

But he quickly qualified it. He described this particular winter as "much milder than previous winters" and predicted it would be shorter. "It's going to be followed by a spring and then a glorious summer. So don't fear," he told viewers on The Claman Countdown.

Saylor pointed to a few reasons he's still bullish. He cited 12 cabinet members who support digital assets, growing involvement from the banking sector, and what he called a "Bitcoin president" in the White House. He also noted that institutional support is far stronger now than during the 2022 bear market.

He followed up on X with his own summary: "We may be in the middle of a crypto winter, but spring is coming, and Bitcoin is winning."

Can Strategy Actually Handle This?

Saylor says yes, and he's put a number on it. Strategy has publicly stated it can survive a drop to $8,000 per BTC and still cover its roughly $6 billion in debt. Of the $55 billion in total capital the firm has raised, only $8 billion came from borrowing. The rest was equity. Strategy also holds about $2.25 billion in cash, which Saylor says covers around two and a half years of obligations.

He also announced plans to convert existing convertible bonds into equity over the next three to six years, further reducing leverage.

Even if the company can't keep buying every week, Saylor said it will continue to accumulate at least once per quarter. For a firm that has made 99 purchases and counting, slowing down still doesn't mean stopping.

What Does This Mean for the Market?

Bitcoin is down roughly 46% from its October 2025 all-time high of $126,000. Sentiment indices have dipped into "extreme fear" territory. And yet the single largest corporate BTC holder just bought the dip again, lowering its average in the process.

Whether you see that as conviction or stubbornness depends on where you think the price will go next. But Saylor's willingness to call this a crypto winter while still buying through it sends a specific message: Strategy isn't waiting for better conditions. It's treating current prices as the better conditions.

Sources:

• CoinPedia Strategy's Michael Saylor admits Bitcoin crypto winter after saying it would "never return"
• Benzinga Michael Saylor calls current crypto winter mild, predicts "glorious summer" ahead
• The Block Bitwise CIO says DeFi could lead market out of crypto winter as Strategy's Saylor predicts recovery
• Crypto Briefing Strategy acquires 2,486 Bitcoin at $67,700
• U.Today Saylor: "We Are in Crypto Winter"
• Bloomberg Crypto Winter "Not Coming Back": Saylor (June 2025)
• Fox Business Strategy founder explains Bitcoin is in a "crypto winter" (February 17, 2026)
• ZyCrypto Strategy scoops up another 2,486 Bitcoin as its $48 billion stack remains underwater