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Large volume options sell
It depends upon who the counterparty is. If the counterparty is the OCC, they would most likely call force majeure if their finances were at serious risk.  They could be forced to take a loss but not to be pulled apart.  Villain could always try to take the OCC to court, but then his plot would probably be exposed in discovery. The need to involve the courts is even greater if these are private contracts. If the options were on one security, they would be difficult to sell in one day.  If they were spread across the most liquid ETFs and equities, they could be sold in one day easily, the above solvency problems notwithstanding.