The ESPN 30 for 30 seemed like an abridgement of his book The Outsider.
The one interesting thing the 30 for 30 brought out was how Connors continues to misread his relationships with some of the players. For instance, he noted in his book that he considered Patrick McEnroe a friend and that he was more laid back and fun than John. He even had a photo of he and Patrick sitting together in his book. When PM called him an a-hole in the 30 for 30 documentary, you could see the wounded expression on Connor's face. He did not expect that. It seemed to me from reading the book and seeing the ESPN documentary that even though he is still an unrepentant lone wolf, he likes to think some of the players understood him, respected him, and even liked him.
He also documents his early friendship with Krickstein in the book and admitted that he had not seen Krickstein since then. Connor's last mention of that match in his book was "Are you avoiding me Aaron?" So the 30 for 30 didn't uncover anything new, but seized on how cold Connors could be. Connors revealing that he paid for Chrissie to abort his baby (her choice) is another indication of how awkwardly cold he is with relationships.
Was Connors cheap and classless in the McEnroe and Krickstein matches? IMO, absolutely. But let's be serious, as solid as those two were, they were not championship caliber. Even brother John said he had a bad feeling about the match and went to bed with his brother up two sets and a break in the third. Connors did not destroy either one of those guys' careers.
To understand Jimmy, you have to know that only two things mattered to him: 1. Winning and 2. Giving the crowd everything he had. He says repeatedly in the book it did not matter to him that the crowd booed him for most of the career. The only thing that mattered is that they showed up. And Connors more than any other player transformed the game and put average joe butts in the seat and blew the game up in the US. Is he a d-bag? Yeah, but so are most elite athletes in that GOAT conversation. He is just brutally honest about it.