General Discussion

It's that he makes the typical mistake of having someone (his father, Roy Cohn) teach him a bag of tricks that has (mostly) worked for him all his life to get what he wants, but he's too stupid to come up with any new ones when he's faced with someone who can counter those tired old tricks.

Notice how he keeps cycling through the same boring tactics, over and over: Name calling, taunts, threats (implicit and explicit), silly distractions, lies, whining, bullying, and so on. When all else fails, sue!

The problem is that those tactics work the few times you cross up a random plumber in Hoboken where others can't see. They don't work with a national audience who are watching...and taking notes.