Did you tell him that dealing with a doctor like him was indeed risky behavior?
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Does your policy say that? The insurance company was largely unconcerned with that sort of info on my forced landing. The FAA was a different story. They wanted copies of my certificates (why they can't look it up, they have all that) as well as my flight review signoff and the last annual.
I do believe the insurer asked for the annual info.
We've had verbal indications from at least one insurer who stated that they would not pursue policyholders with expired medicals under this policy. I would get that in writing before flying, however. There are a lot of moving parts with this policy statement, and it doesn't help that the month is about to end. We're working on getting some clarifications and will publish an update as soon as we hear more.