I thought the Don came across as small time and naive. He and the rent a crowd sycophants he surrounded himself with thinking they’d made it to the big league by getting to the Check-a-Trade final
Definitely daddy’s money. The guy is a fucking moron.
Incidentally, I hadn’t made the connection until I saw the Don with his family at a game in the first episode, but I used to teach his son. A thoroughly unpleasant individual.