re: United Airlines Settlement

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and a jury probably would've given him $40k, max

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Eh, I think a jury would have given him much more than that. Keep in mind, though, that I'm neither an attorney nor have any legal experience.

TL;DR: UAL went full retard.

After hearing of the incident, I checked UAL's Contract of Carriage (you can read it HERE). UAL can only voluntarily or involuntarily remove you from an overbooked flight before boarding (Rule 25). Since the plane had already been boarded, Rule 25 can no longer be applied to remove a passenger even if the plane is overbooked; the only way to get a passenger off the plane at that point is by sweetening the voluntary deal to take a later flight or through Rule 21: Refusal of Transport. UAL could use Section H of Rule 21 as a defense, but such a defense could fall apart pretty quickly considering the number of witnesses with contrary testimonies.

Considering UAL broke the contract that they wrote and that their customers never read, I'll consider UAL lucky that the guy isn't the chairman of their board right now.