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If it was a court settlement (and sued implies at least some kind of case, even if it was a formality), and the settlement stipulated a doctor's...

In the context of the screenshot of the conversation that appears to be something Kat told her ex-boyfriend about Phil. Maybe some shit Phil made...

Aireaid Lord car accident lore Edit: this seems to be in 2004 or 05. Phil graduated in 2000. Maybe he has been in two near fatal car accidents?