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In the past, I’ve never found Paulie Gualtieri to be a particularly empathetic character; though I respect his devotion to routines and stinginess, I simply cannot relate. But now that I spend so much time reminiscing about mundane shit from the past — knowing when my next flight would be, half-watching a baseball game, experiencing mild self-hatred in the Target dressing room because the lighting makes my nose look so crooked — I appreciate him a little bit more.
“Remember when” is not, as Tony declares, “the lowest form of conversation,” nor is Paulie’s reliance upon it entirely, as Beansie suggests, evidence that reminiscing about the past is all Paulie really has. Although I think a lot of Tony’s personal discomfort comes from the fact that the endless “remember when”ing rubs his face in his general malaise about feeling like it’s all downhill from here, the episode gradually reveals that Paulie’s nostalgia is a bit more complicated than it seems, as it’s time-bound by a very specific regret: killing Big Pussy.
I think you can understand the tense boat scene two different ways: The first is that Paulie is anxious that Tony will kill him (over the Ginny Sack mole joke gossip, of all things.) The second is that being on the boat jogs loose Paulie’s continued remorse about killing Pussy, throwing him entirely off-balance. It’s probably a both-and situation — Paulie’s personality is marked by self-absorbed paranoia and intense loyalty in roughly equal measures — but the latter reading is, I think, the more compelling to explore.
Not only do the apparitions continue once they return safely to dry land, but it’s also worth noting that Paulie has always had a tendency to dwell on his regrets, and to take stock in the supernatural (or what he perceives as the supernatural) as he tries to make sense of them: his recurring 3am nightmares after Christopher is shot, the vision of the Virgin Mary that leads him back to Nucci. I doubt Paulie’s been obsessing over guilt about Paulie for all these intervening years. But the vividness of this round of hauntings suggests that his remorse never fully left him — that it ebbs and flows, spiking in response to particular events, whereas Tony seemed to move on quickly, maybe because he followed it up with so many other things to feel terrible about.
Still, Paulie represents one possible future for Tony: a man haunted by regret, a man who has nothing to show for his life but his job and his image. And Junior represents another: a man confined to an institution and cut off from his community, but still finding ways to replicate its destructive dynamics. As he wreaks havoc throughout the ward, we finally get to see Junior as he must have been at his peak — menacing in his own right, not as someone else’s puppet; obsessed with securing control both because he craves it for himself and wants to deny it to others — and therefore we finally get to see him as he must exist in Tony’s memory, finally get to experience the gulf between our image of Junior and his.