re: #140 wheat-dogghazi-mailgate

I think his master plan was to ask for an astronomical figure he knew he’d never receive, expecting Gawker would settle out of court for a lower sum. That strategy has clearly failed.

Right, he didn’t realize that making the figure SO high worked to make settling impossible. If I put myself in Gawker’s shoes and assume the worst case scenario, that I stand a very good chance of losing a libel case, the fact that they’re asking for $66 million means I’m probably not going to be able to settle for less than $6.6 million, or 10%. So why wouldn’t I spend $600K throwing shit at the wall?

Whereas if Chuck had asked for a much more reasonable $1 million he might have stood a plausible if still very unlikely chance at getting an offer to go away for $100K or so.