But it's only possible when you're well-capitalised and not as dependent on cash flows. See also the Kelly criterion, which makes it logical for one actor to offer and another to pay for insurance, despite the fact that both sides cannot have positive EV.
> despite the fact that both sides cannot have positive EV
Maybe for the thing insured, but dependencies can cause ripple effect costs which can be very high, so both sides can have positive EV when considering the whole (not just the insurance). I think you are assuming all transactions are zero-sum? Not something I know much about, so quite probably I just misunderstand your comment.
