So that Tony had Hesh's girlfriend murdered is pretty obvious to me.
You're reading WAAAAAY too much into that. Tony didn't have Hesh's girlfriend killed.
Tony really liked Hesh. Yes, he could have beat Hesh out of the $300K, just as one of Tony's guys suggested, but he didn't. He paid Hesh back in full because he liked him and respected him. That's why Tony had a look of satisfaction on his face - because he did the right thing and he knew it.
