Bitcoin (BTC) entered Friday's largest monthly options settlement of 2026 in a losing position. At 8:00 AM UTC on May 29, roughly $9 billion in BTC options expired at Deribit — and the structure heavily favored the bears.

The setup was built over the preceding 24 hours. On Thursday May 28, BTC retested $72,500 for the first time in six weeks, triggering $342 million in liquidations tied to bullish leveraged positions. A brief relief bounce brought prices back to $73,500 but failed to alter the options picture.

Deribit held approximately 70% market share for the May monthly expiry, with $3.4 billion in call open interest and $2.91 billion in puts. With BTC parked below $74,000 at expiry, only $306 million worth of call options finished in the money — against $1.05 billion in puts targeting $74,000 or above. That gap handed bears a structural advantage of roughly $744 million. Even in a scenario where BTC had reclaimed $74,000 before the 8:00 AM UTC cut-off, puts still outpaced calls by $265 million.

Put-to-call volume on Thursday held at 0.8 — a neutral read, with $1.57 billion traded in calls against $1.29 billion in puts. That neutral ratio is notable: it means traders were not aggressively positioning for further downside, but they also weren't bidding up protection from a bounce.

Looking to June, the picture stays subdued. The $80,000 call for the June 26 expiry traded at 0.0103 BTC ($757) on Thursday, implying an 18% probability that BTC reaches that level within 28 days.

Macro context compounded the options setup. US-listed spot Bitcoin ETFs recorded $1.07 billion in net outflows over the two days preceding the expiry. Corporate holders also pulled back: Sequans Communications (NYSE: SQNS), a Paris-based IoT semiconductor developer, announced Thursday it would fully liquidate its 658 BTC (approximately $48 million at announcement) after less than a year pursuing a crypto treasury strategy. The company had raised $384 million in June 2025 to fund the position; BTC has fallen more than 30% since then. Trump Media and Technology Group (DJT) and several publicly traded miners have separately reduced Bitcoin exposure in recent weeks.

Bears held the structure, the liquidation catalyst, and the macro narrative heading into settlement. Whether that combination produces a sustained move lower depends on what BTC does with the cleared open interest heading into June.