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My childhood best friend is one of my favorite people in the entire world, and you can tell my love for her and her family is deep because it remains intact in spite of the fact that they are Monopoly people. I do not mean that they don’t recoil when someone suggests playing Monopoly (which is weird enough in its own right); I mean that they voluntarily play obsessive, non-contentious games for literal days on end. I’m not sure if their ability to keep the competition copacetic is a sign that they’re more highly evolved than the rest of us or a sign of hereditary psychopathy — but those are, it goes without saying, the only two options, because Monopoly, not hunting people for sport, is the most dangerous game.
“Sopranos Home Movies” understands this objective truth (although, to be fair, it also makes Monopoly and murder a little hard to separate out from one another). Of course Tony and Janice cannot get through America’s most infuriating board game without a fight; you could not design an activity that would bring out more of their cutthroat, manipulative, rapacious tendencies if you tried. Everything is Monopoly for them — even what seems like a fun group activity is built on a foundation of competition over scarce resources (board game properties, their mother’s love, influence within the Family) that makes it impossible to sustain camaraderie for any real length of time.
The only real surprise here is that Bobby — poor, sweet Bobby — manages to get dragged into their familial muck this time. After years of trying to defuse every conflict through his unique combination of kindness and haplessness, Bobby gets involved in a hands-on way, jumping across the table to whale on Tony and defend his wife’s honor. Whatever you make of Tony’s explanations for it — drinking threw him off balance, he’s still not fully recovered from being shot, etc., etc. — Bobby proves dominant, although his victory is short-lived. Janice isn’t flattered but instead furious that he’d put his career at risk; Tony seizes on this paradoxical vulnerability to manipulate Bobby into executing his first kill.
Of all the weird gems from the past this episode hands us, the most intriguing is that a prolific hitman — “The Terminator” — spawned Bobby, “a virgin.” This detail sheds light on why Bobby is part of the crew despite his unwillingness/inability to do anything too appalling, and it introduces us to yet another complicated father-son legacy like the ones we’ve spent the last few episodes marinating in. Bobby never says that he consciously tried to be different from his father — and the fact that his father was so respected and terrifying grants him the ability to be unimposing and unbloodthirsty without being ostracized, so it’s not like Bobby has fully liberated himself from his inheritance here — but even if it was an accident, it’s clear that he’s unashamed by his failure to live up to his father’s achievements.
Tony outmaneuvering Bobby into sacrificing this point of pride, simply to save his own bruised ego, is one of the most brutal moments in the series. Bobby’s first hit is — like Christopher’s initiation ceremony — a little anticlimactic; the real violence comes in the moment afterward, in which Bobby has to face his young daughter. It would be sad enough if Bobby were simply a nice enough guy we’d grown to feel affection for, but knowing that this moment initiates him into a club he’d deliberately avoided joining makes it devastating. He struggles to reconcile the fact that he is both a murderer and a father — and does so knowing that his father once did the same, with apparently minimal friction. He’s forced to reconsider his knowledge of himself as a parent and his knowledge of himself as a child at the same time, and he’s not sure he can live with what he’s discovered.
Bobby’s soul was one of our last remaining tethers to the possibility of a better future: here’s a man who managed to be unlike his family for decades, and he gave in not because it’s his fate but because the threat of not belonging to the only community he’s ever known is more powerful than the risk of losing himself. It’s his point of no return, and it’s horrifying in its black-and-white clarity. Other characters’ passages into irredeemability are far more ambiguous and debatable (was that really the end for them, what about that flash of possibility afterward, what about this far worse thing they did later). Tony’s downfall is the most ambiguous of all — but watching Bobby struggle to hold his daughter and hold back his regret makes me think, in retrospect, that it’s “College,” that Tony’s ability to jump seamlessly between murder and parenting was the moment we were supposed to realize that he could never be saved at all.