> Although it's conceivable there's a surprise legal finding, companies like OpenAI and Anthropic are confident enough in how it will go that they are willing to insure you for any lawsuits, which would be ruinous for them if they consistently lost.

I don't think this is the right interpretation, at all.

They can act confidently about this because corporations can't go below zero; the downside of the bet is so far in the red, in that zone of bankruptcy, that it actually makes the bet work even if they internally believe that they're likely to lose in court.