Stern is actually a lot like Trump so its no coincidence that they are friends. Stern is really shallow, self absorbed, incredibly insecure, neurotic, and self loathing. He also has an ego the size of Jupiter. You could use many of these adjectives to describe Trump. I think the difference is Stern is way more self aware about who he is as a person and would never subject himself to this kind of scrutiny and would never run for president as a result. He likes doing his show and making a shit ton of money and still somehow being influential even though he's on satellite and not terrestrial radio anymore.
So do I think Stern is a great guy? No not really. I would hate to have to work or hang out with a guy that neurotic and self obsessed. But I did think his show was good (well at least the interviews) and his job is to be entertaining and I was always entertained by the interviews he did. He's not running for president either so I'm not going to be as hard on him as I would Trump unless it comes out that he sexually assaulted women for the majority of his adult life like Trump apparently has.