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The Sopranos: “Chasing It”

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“Chasing It” (season 6, episode 16; originally aired 4/29/2007)

In which Tony will never catch up

Of the nine episodes that make up the final batch of The Sopranos, “Chasing It” is the only one that I’ve heard even mild criticism for from the show’s fan base. Okay, sure, there’s a portion of the fan base that finds the entirety of this final season to be a missed opportunity, a chance to just bloodily mow through the cast with impunity that the show didn’t take for some reason. (These viewers likely would have had a bruised and battered Tony, machine gun in hand, Chekov’s grenade by his side, battling it out with New York from the comfort of his own home.) For the most part, though, I’ve found that fans enjoy this stretch of episodes, the long downward spiral to whatever the end holds. And maybe that’s why “Chasing It” sticks out a bit. It’s not bad by any means. Indeed, it’s quite a good episode of The Sopranos. It’s just surrounded by some of the best episodes of TV ever made. It’s a little hard to get excited about Tony’s gambling debts when that’s the case.


The chief criticism of the episode is that Tony would never have gotten involved this deeply in gambling. (Indeed, at one point earlier in the show’s run, he cautions against how gambling can take over your life and make you do stupid things.) This is a criticism I’ve never bought. The show has so successfully established that at this point, the Tony who survived being shot by Uncle Junior is a rasher, more impulsive Tony that I largely buy his giving in to this particular vice. Plus, look at the things he’s wagering: The horse he bets on in the race is named “Meadow’s Gold,” something he considers a lucky omen, even if said horse eventually loses. Tony is betting that he’s built up such a large lead that the universe can never come calling, that his survival—and, indeed, his continuing to thrive—is a “sure thing,” as sure as that Chargers quarterback with the hairline fracture in his leg going down.

I’ve been advised by many that the best way to watch season six is to watch it straight through. In that fashion, the mirroring and symbolism David Chase and his writers build up over the course of 21 episodes becomes more apparent. And while I’m sure that’s the case, I’ve always felt the season plays slightly better with that break between “Kaisha” and “Soprano Home Movies.” I see it this way: If those first 12 episodes are about a man who desperately tries to change, who tries to hold off his own worst impulses to become something “better” (whatever that means for Tony Soprano), then these last nine episodes are about how that man, having realized how much less exciting it is to be that responsible adult and to commit himself to his marriage and the prospect of change, cycles into self-destruction. In that sense, a gambling problem is incredibly appropriate: Tony Soprano is gambling with his life, and he’s building up a bigger and bigger debt to the house. Worse, he’s isolating all of the lifelines that might have gotten him out of trouble in the past.

Take, for instance, Hesh Rabkin. It’s hard for me to imagine there were any Sopranos fans really concerned about what would happen to Hesh at the end of it all, but this episode spends an inordinate amount of time with him. In fact, it’s likely one of the two or three most Hesh-heavy episodes in the series’ whole run, and it ends with him and Tony’s relationship at least temporarily soured. It’s not hard to imagine that this is where the two, who’ve always had an easy camaraderie, part ways simply because Hesh insisted he start getting back the money Tony owed him. Hesh, more than anyone, understands how deeply Tony could be burying himself with gambling and his lifestyle. (At one point, he rants to his girlfriend, Renata, about the cost of Tony’s boat, which is massive.) Yet Tony doesn’t want to hear it. He’s not interested in the ways he could be dooming himself, not when there’s a great big present to go out and live in.

Or maybe Hesh’s words strike such a chord in Tony because he already senses that the good run is coming to its end. He opens the episode making a huge sum of money off of a bet, but when he tries to push those chips onto another bet, he loses. The hot streak is over. The only win he counts in the episode comes from the inside knowledge he has on the football game, and in that case, he’s unable to truly capitalize because he didn’t have enough money to place on the game to really make a difference. Throughout, he keeps coming up with new funds, then losing them on bets. What he’s doing here isn’t really addiction, per se, nor is he really desperate to find a way back to solvency. When he needs to give Hesh the rest of his $200,000, Tony is able to provide it in a paper bag. No, what Tony is trying to do is find a way back into the universe’s good graces, back onto the never-ending gravy train that propped him up for so long.


Few TV series in history have conveyed existential dread as well as The Sopranos did, and “Chasing It” seems to have as its primary motive the reestablishment of that dread when it comes to Tony himself. One of the overriding ideas in the show—and particularly one of the overriding ideas in the final two seasons—is that bad stuff happens to people around Tony, but rarely visits the man himself. To that end, he’s unable to, say, comprehend that when Hesh is mourning the suddenly passed-away Renata, the settlement of their debt isn’t going to make everything all right. Oh sure, on some level, Tony understands that what Hesh is going through is incredibly painful, and that the sorrow the old man feels is something Tony hasn’t really been privy to. But on another level, he really does seem to think Hesh is the guy from his anti-Semitic jokes about how all Jews care about is money. He says he’s just joking around. He probably believes that’s all it is. But he’s reducing a very old friend to something mean and negative and hurtful, and he doesn’t seem to understand why that would further push Hesh away from him—Hesh, who always gave him such thoughtful counsel.

At one point in this episode, Melfi tells Tony that the way he talks about Hesh doesn’t seem to describe a friend. And she’s right. Tony wouldn’t treat someone he truly cared about the way he treats Hesh. But he also wouldn’t be so belittling toward Carmela’s spec home—which she finally sells to her cousin Brian—if he was truly on her side, nor would he have contemplated murdering Paulie last week. Increasingly, Tony seems isolated and paranoid, driven into a cocoon of his own making from which he peers out at everyone around him and assumes they’re only out to get him. In some cases, that’s probably true. After all, if there’s anyone else as isolated and paranoid as Tony at this point, it’s Phil, and he represents a real danger to Tony and his business. But many of the others Tony suspects owe at least an uneasy allegiance to him, and he seems to treat them as beneath him. To be a friend would require a certain level of equality between both participants in the friendship. Tony increasingly can’t see anyone as his equal. He’s outlasted anyone who could claim to be, and now, his naked contempt is lashing out at those who’ve always had his back.


A long time ago in the comments, someone suggested that the theme of each season was Tony’s relationship with a different character. To grab an obvious one, season four was about Tony’s role as a husband to Carmela and how thoroughly those two people undermined and destroyed each other, often without meaning to. The conclusion of this argument was that season six was about Tony’s relationship with himself, about how he’d grown so far apart from everyone else in his circle that he’d essentially become this planet unto himself. Others fell into orbit around him, but he seemed to not care terribly about their concerns, so long as his gravitational pull remained strong. In the past, he might have taken Hesh or Beansie’s counsel on some matter or another. Now, he listens to that counsel and mostly discards it. He is a man unto himself.

This is one of the things that makes “Chasing It” kind of a letdown from the previous three episodes, I think. In all of those three, there’s a wonderful electricity to the idea that Tony might not know when to stop, might do something really terrible. He eggs Bobby on over Monopoly, then sends him out to kill someone who doesn’t really need to be killed (and certainly not by the Jersey mafia). He toys with the idea of ridding himself of Christopher once and for all. He seriously toys with the idea of ridding himself of Paulie once and for all. But he never does anything actually dangerous. He always steps back at the last minute, and the more we see him through the eyes of others, the more we see not only just how dangerous he is, but also just how pitiful he is, on some level. (In this episode, our brief glimpse of Tony through another’s eyes comes from Vito Spatafore Jr., of all people, who seems to see him as a well-meaning yet completely clueless elder. We also get a short scene where Hesh spots the coiled menace beneath Tony’s otherwise genial exterior.) The idea of Tony finally just killing someone has been dangled so many times that it’s starting to lose its potency, and the episode itself is often a long wallow with Tony in a state where he’s realizing that whatever “it” is, it’s slipping away.


But there’s another Tony we see here, the Tony who tries to put Vito Jr., on the right path and mostly fails. Tony has always cared at least somewhat about the children surrounding him, probably because of his abiding love for his own kids, and he’s much better with Vito Jr. than Phil is, who mostly just mocks the kid about his father’s sexuality. But he still doesn’t get it. His lectures to Vito Jr. may as well be directed at himself—it’s not accidental that he brings up the “go about in great pity for yourself” quote when he’s upbraiding the boy—and his ultimate solution to the problem of what to do about the kid is the one that causes him no pain whatsoever. He promised Marie he’d help out where he could, but he bristles at giving her the substantial sum it would cost to go to Maine, both because his gambling losses would make a payout of $100,000 hurt more than usual, and because he just doesn’t care all that much, beyond the theoretical. I really do believe in an earlier season, Tony would have hemmed and hawed and eventually given Marie that money. (Then again, in an earlier season, he wouldn’t have lost so much gambling.) Here, he sends men into her home at night to drag Vito Jr. off to one of those boot camps for troubled kids you see on Maury. Tony sends his problems off into places where he doesn’t have to think about or see them—often literally.

In the middle of one of the two Tony-Carmela scenes that dominate the episode, Tony tells his wife that he’s chasing after something, something that he can almost get his hands on before it slips away. What is it? she asks, understandably. Money? Or maybe it’s the high from winning, as Melfi suggests. Viewers might also be tempted to think he’s going after power or control or the ability to just have everybody around him do whatever he says, whenever he wants it. But Tony can’t put what he’s headed after into words because it’s ineffable by nature. He’s chasing the thing all of us are, the thing that we think will bring us happiness once we find it. He’s chasing the feeling he felt when he sat in that wheelchair outside the hospital and realized every day was a gift. He’s chasing the knowledge that he too will die and that every day until he does should be treated with the greatest of care. But he’ll never find it where he’s looking, where all he can see are distractions. He might find it in Melfi’s office, as his coma vision suggested, but he’s mostly stopped going. He might find it with his wife and kids, but he’s mostly pushing them away. Tony is chasing something in himself, and if we know this man by now—and we do—we know that’s the last place he can find it.


Stray observations:

  • Speaking of chasing it, A.J. spends the episode trying to solidify his relationship with Blanca by proposing. At first, she accepts, but then, she breaks up with him. A.J. has been clumsily trying to chase after the idea that if he really breaks from his parents, he’ll be a new man. Blanca and Hector represent that for him, as does his job at the pizzeria. But that’s not really true. Blanca’s reasons for leaving him aren’t adequately explained, but the tension evident in her every time she’s around Tony and Carmela should be self-explanatory.
  • If you’re a fan of The Sopranos, then you should check out Alan Sepinwall’s new book, The Revolution Was Televised, which has an excellent chapter on the show’s birth, life, and death that sheds lots of light on questions about how the show came to be, particularly in regards to this final season. (For one thing, it sure seems like Chase would have answered the question of “What happened to the Russian?” in this very episode, when Tony talks about going to see Slava.) There’s also an interesting tidbit about the finale that I’ll save for the “Speaking With The Fishes” section.
  • The object Carmela throws in her titanic fight with Tony is the one she said cost $3,000 way back in season four. (Also, has there ever been an American television show better at depicting the kinds of marital fights that come when two people know each other this well than this one was?)
  • Nancy Sinatra’s appearance in the episode is bizarre and kind of unnecessary. I did like that she and Phil apparently go way back.
  • The sequence with Vito Jr. taking a shit in the shower is appropriately disgusting, even as the end product looks completely unrealistic.
  • It somehow hurts even more that A.J.’s heart is broken to the strains of an instrumental version of “Livin’ La Vida Loca.”
  • Hesh has always been one of my favorite tertiary characters on the show. I like the way that this and other episodes that focus on him offer this entire other life that we might have gotten to see had the show been called The Rabkins.
  • Meadow, who hasn’t been in this season as much as you might expect, briefly pops up to let us know things are going fine. If we know this show, we’ll know that can never last. After all, that horse did lose.
  • “Like a pebble in a lake. Even the fish feel it.”—Christopher Moltisanti, philosopher.

Speaking With The Fishes (spoilers):

  • All right, so in Sepinwall’s book, Chase says that he’s only ever read one interpretation of the finale that got at what he’s going for. He doesn’t hint within the interview about what that was, and I doubt he ever will (since he’s intent on keeping his own personal interpretation of events to the grave). But I think it’s fascinating to imagine there’s this one article out there that made David Chase nod and say, “Yep. They got it.” (For the record, I’m guessing it’s not the giant “Master of Sopranos” essay, simply because the points developed there have been brought up time and again in many other places for it to have been so uniquely singular a theory. I’m not saying Tony’s not dead, just saying I imagine the essay is more obscure than that one.)
  • Blanca ending her relationship with A.J. will send him into the tailspin that dominates much of the rest of the season. The next three episodes, in particular, are filled with depressed A.J. Whether or not you like them—I do—will depend on how capable you think young Robert Iler is.
  • In many ways, “Chasing It” is a pivotal episode for the season, in that it depicts the end of Tony’s lucky streak. Karma’s about to come calling.

Next week: Yes, we’ll be around the day before Thanksgiving, as Tony tries to deal with A.J. and asks him to “Walk Like A Man.”

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