What I got from Henry in that last part was him confessing how much he let himself down. Him going from living the life he always wanted to ending up living the live he never wanted. He had it all he was living the life as someone people feared & also respected and all of that got taken away. I think maybe if he had listen to Paulie in the beginning and not go through with narcotics he wouldn't be in the situation he is now in. all of this would of been prevented, I feel like in the end Henry got greedy and that is why he did so many different gambles & illegal things just to earn a buck. In a way I felt like he was Jimmy, in the end Jimmy was at his worse because of the hijacking and whacking everyone he became greedy. And that is what Henry did & giving up people he was close with. In the end when Henry refereed to himself as a schmuck he was referring to his father, a man that actually had to work for a living and that was always the life Henry didn't want. So i guess he felt like this was a punishment getting a second chance to live and to live the life he didn't want, a life of an average guy, i life with no more thrill no more excitement.