My understanding is that the case was flimsy enough that no "hardcore" lawyers wanted to represent him. It's not just a matter of money; their record (and, therefore, future earnings) are on the line.

A more "hardcore" team will keep telling him he can win on appeals, and bill accordingly.

His case was handled as well as any lawyer could have. He signed the deal and then tried to change his mind. That's not how contracts work, and the legal system and status quo have strong interests in keeping it that way.