I have the impression that Klein thinks his legal win against Matt Hoss, was down to his own brilliance and charisma. Rather than the fact that Hoss was a broke weirdo who could barely fund the lawsuit. Even though Klein had the law and a large GoFundMe behind him he still cycled through lawyers, and ignored legal advice such as not talking about the case.
He said on an old stream he can't get insurance against lawsuits (because of the Matt Hoss case), so he's completely on the hook for this. I know little about the US legal system but I do know they rarely award costs against a plaintiff unless their case was obviously bad from the beginning (eg Akilah Huges, or Vic Mignogna), and the court has already said there's a case. So Klein is going to end up out of pocket even if he wins.
Also he's a dumb fuck that can't take advice, what kind of legal team are going to work for a guy that calls the judge a 'crusty old fuck'.