According to insiders, Trump is terrified of going to jail. I think that Trump keeps violating the gag orders because he honestly believes that there will be no consequences. You have to remember, that this is a 77 year old man who has done whatever he wanted, illegal or immoral, his entire life and gotten away with it. There has never been any consequences. That's why he fought the outcome of the 2020 election so hard. He refused to accept that he lost. He still denies losing to this day because he cannot accept that he didn't win.