Tony goes to visit Hesh, and he complains about Phil's smug attitude at the dinner, and how Tony thinks it's still due to Phil's brother getting whacked by Tony B. Hesh thought that was resolved, but clearly he doesn't know how long Phil can hold a grudge. Tony muses that his key guys might have an agenda other than Tony's or the Family's best interests. Hesh asks, "Lonely at the top, boychik?" Tony thinks it's nice being with Hesh, since there's no pressure, no one asking him for anything. Tony suddenly sits up, remembering that he has something for Hesh, and pulls out a Cleaver baseball cap. How many of those did they have made? Hesh says carefully that he was actually hoping for a payment on the $200,000 bridge loan. Not a good move right after Tony talked about how Hesh never pressures him for anything. Hesh tries to backtrack, saying that he knows Tony's good for it. Tony starts getting pissed off, and offers $3000 as an interest payment, sarcastically noting that he doesn't want Hesh eating cat food while gesturing around to Hesh's well-appointed home. Hesh tries to refuse the money, realizing that he's offended Tony, but Tony presses it on him, tries to make nice, and then leaves.
Once Tony's gone, Hesh walks into his bedroom, where his girlfriend, Renata, is sleeping. In a nice piece of continuity, Renata is African-American, because we know Hesh has a predilection. Hesh complains that he's only asking for the money he's owed, and yet Tony made him feel like a schmuck. Hesh points out, as Renata makes sympathetic noises, that Tony throws away his money on stupid things like his boat.
Tony glances at his watch during a session with Melfi, so clearly it hasn't been all that productive. Tony wants to talk about how Jews are good with money, which Melfi isn't going for. Tony veers onto the subject of his gambling, and his losses of late. Melfi wonders why he keeps gambling if he's losing so much money. Good question, Melfi. Tony says that he needs the risk, and Melfi wonders, "What are you chasing? Money, or a high from winning?" Tony doesn't answer. Right when they might be getting somewhere, Melfi moves on to talk about how Tony has missed a lot of appointments, and even though he does call ahead or pay for his time, it's not acceptable, and she's let it slide for far too long. Tony admits that his time with Melfi is "an oasis in [his] week," which Melfi doesn't really like to hear, since therapy shouldn't really be comfortable and pleasant if it's working. Melfi wants Tony either to make a commitment to continue seriously, or stop coming to see her. Tony seems to realize that all of his support systems are crumbling -- Christopher is more interested in his movie than anything else, Bobby beat the crap out of him, Paulie's got a big mouth, he feels he can't rely on the rest of his crew, he's loath to involve his family in the Family business, Hesh seems to just want his money, and Melfi is withdrawing her unconditional support as well. And not that Tony doesn't deserve it; you can't treat people like your servants all of the time and then expect they'll always be there. I'm just pointing out how things are unraveling for Tony, because I think it explains some of his actions later in the episode.