No one wants to look like an idiot with a client that goes against legal advice when it suits them or just goes and contradicts public statements made on the client's behalf. Trump's reputation in that regard precedes him so he has no one to blame but himself if he ends up with 2nd or 3rd tier representation. He also has a reputation for having to be sued for fees if he decides he didn't get the outcome that he wanted from anyone with whom he contracted for a service. Generally, he has lost those cases because often the fault was his own. Kasowitz is undoubtedly on a replenishing retainer since Trump has been in perpetual litigation for decades. His counsel probably doesn't care whether the lawsuits have merit or not. It's a steady income.