Bitcoin Tumbles As Strategy Slammed, Faces Massive $10 Billion Option Expiry

Moments after the cash market opened, bitcoin plunged almost $3,000 in a matter of seconds to $58,000, on no news, sending the price to the lowest level since Sept 2024. 

This was a strange move for bitcoin because while stocks do tend to move rapidly at cash open as that’s when options restart trading (as we have noted, in recent months most investors are trading almost exclusively in options and avoiding the underlying securities completely), bitcoin trades within its own ecosystem that is open 24/7 and is – or rather should be – far less reliant on key stock market time triggers. 

Instead, the trigger for the drop was not bitcoin but rather its biggest treasury sponsor, Strategy, which plunged as much as 8% in what now appears to be a coordinated effort to send MSTR stock sharply lower using puts (hence the move at exactly 9:30am when option trading started), which in turn has led to lower prices on its various tranches of perpetual preferred stocks, and ultimately, lead to more bitcoin selling on fears Michael Saylor will have to sell even more bitcoin. 

However, today it’s not just MSTR that is depressing bitcoin: the largest cryptocurrency is facing a massive options expiry that risks putting more pressure on a market already struggling with fading institutional demand and macroeconomic headwinds.

According to Bloomberg, about $10 billion of notional value in Bitcoin options is set to expire on Deribit, the largest crypto options venue, at 4 p.m. Friday in Singapore. Because most of those options are bullish bets and Bitcoin has been falling, there’s potential for traders to turn defensive or outright bearish. 

“This is a book that has been positioned for higher prices over the medium term, now being marked against a spot that has slipped,” said Jean-David Pequignot, chief commercial officer at Deribit. “The consensus long-call positioning has drifted offside.” 

After dipping as low as $58K, the lowest level in almost 2 years, bitcoin was trading below its 200-week moving average, a technical level that can signal a prolonged bear market.

The Bitcoin options expiring on Deribit represent about 37% of open interest, with the ratio of puts to calls at 0.83, according to Pequignot, indicating more bets are on Bitcoin appreciating. 

The bulk of call open interest is now out of the money, meaning the contracts have no intrinsic value at current prices. Puts, by contrast, are clustered around $60,000 to $65,000 and $70,000 to $75,000, and mostly in the money.

Of course, just because there is a big expiry doesn’t mean more selling is guaranteed: “expiry mechanics clear positioning; they do not set direction,” said Adam Haeems, head of asset management at Tesseract Group. But the key issue is still a call-skewed market falling into thin quarter-end and summer liquidity, he said.

“Thin books plus a concentrated expiry mean Friday’s move likely overshoots in whichever direction flow tips first, then mean-reverts once dealer hedging unwinds,” Haeems said. If dealers finds themselves in a sharp negative gamma position, then any subsequent moves in bitcoin will be significantly amplified. 

Any sharp move around expiry may say more about positioning than a lasting shift in trend. Haeems said the more important test will come in the first full week of July, after the quarterly book has cleared and leverage has been reduced.

Meanwhile, the flow picture continues to deteriorate as US-listed Bitcoin funds posted almost $3 billion of net outflows in June so far, and that ignores the relentless pressure on Michael Saylor’s Strategy and its various tranches preferred securities.

Griffin Ardern, co-founder of Primal Fund, said option traders’ longer-dated bearish bias toward Bitcoin has intensified, while hawkish Federal Reserve commentary and elevated Treasury yields suggest investors are pricing in tighter liquidity.

“Under conditions of contracting liquidity, BTC typically does not fare so well,” he said.