That definitely is an interesting way to put it and there is a lot of truth in that. However freedom is still freedom and in prison there surely is NO FREEDOM. I think that perpetual grin was because while he was trapped by lost enforcement and boxed in, he still was FREE and free to continue to be in complete control (Relative) of LCN which is what he always desired.
Agreed. That grin also meant he was getting away with boatloads of crimes.