There are several clues in "Chasing It" that suggest Tony had Renata killed.
The idea that Tony would murder over his debt to Hesh is explicitly raised throughout the episode:
1. Tony mentions to Hesh that all his key guys are "murderers." (11:22 in DVD)
2. Hesh suggests to Eli that Tony might kill him rather than pay the debt (Scene at 20:50).
3. Hesh is concerned about Renata's safety as well (Scene at 30:47).
In addition to these explicit suggestions, "Chasing It" is packed with hints suggesting that Tony had Renata killed, most notably through allusions to Godfather 1.
1. CHASING IT'S ALLUSIONS TO GODFATHER 1.
In Godfather 1, the Corleones cut the head off Woltz's horse, which Woltz discovers in his bed. Did Tony have Renata killed for Hesh to discover in his bed? Consider the following.
a. Horse heads in Hesh's house.
Godfather 1 established the horse head as a symbol of the Mafia's callous violence. In "Chasing It," we see horse heads throughout Hesh's house. There is a small one on the table between Hesh and Tony when they sit down at 10:37, and another is to Tony's left in the foreground. In the same scene, when we see close-ups of Hesh, a horse statue is behind him, with the horse's head protruding out behind Hesh's. Later, we see a horse head statue over Hesh's right shoulder when he's reading, before Tony and Bobby come to his door (30:47). In the final scene, when Tony drops off the money, there is: (1) a horse head statue in the foreground, (2) a horse statue to Hesh's right, where the head is emphasized by the reflecting light; and (3) when we get a close up of Hesh, we can see the head of a horse statue protruding from behind his right shoulder.
b. Parallels between Woltz and Hesh
There are parallels between Woltz and Hesh: both are Jewish and earned their wealth in the entertainment industry. Both also love horses. Hesh of course owns a horse farm, and in addition to the statues referenced above, has several horse paintings in his house.
c. Parallels between the horse in Godfather 1 and Renata
In Godfather 1, Woltz finds his horse dead in his bed. In "Chasing It," Hesh finds his "whore" dead in his bed.
One may object to calling Renata a "whore." But on the Sopranos, the term "whore" does not necessarily refer to a prostitute. It refers to a woman who sleeps with older or married men. For example, in the Season 2 episode "Knight in White Satin Armor," Carmela refers to Tony's mistress Irina as a "whore." In Season 3, Ralph and Johnny Sack refer to Tracee, a stripper and Ralph's mistress, as a "whore." In the Season 4 episode "Whitecaps," Carmela tells Tony he's made a fool out of her for years with his "whores." In the Season 5 episode "In Camelot," during the flashback, Livia Soprano refers to Johnny Soprano's mistress, Fran, as a "whore." (Ironically, in the same episode, Fran refers to Hesh as a "whoremaster.")
In Sopranos parlance, Renata is a "whore." We can presume that earlier in his life, Hesh was married to a Jewish woman with whom he had a traditional family---we are reminded of this during the episode by the appearance of Hesh's daughter Beth, a middle aged Jewish woman. While Hesh and Renata appear to have legitimate feelings for one another, the relationship is plainly transactional. Renata is sexually attractive (especially to Hesh, who has a fetish for African-American women). Hesh is wealthy and can provide Renata with a luxurious life (immediately before Hesh sends Renata upstairs when Tony arrives at their house, Renata is wearing a gold necklace, a large ring, and is putting on a gold watch). Simply put, Renata satisfies Hesh's sexual desires and Hesh satisfies Renata's material desires. (While maybe pure coincidence, the actress who played Renata was 39 and the actor who played Hesh was 78 when "Chasing It" first aired, conjuring up the saying "she's half his age.")
"Whores" and horses are linked throughout the Sopranos. The link is primarily established through Tony's relationship with Ralph, which is irreparably damaged over Ralph's murder of Tracee, his "whore," in the Season 3 episode "University." In this episode: 1. Sil refers to Tracee as a "thoroughbred." 2. Ralph and Tracee are drinking Rolling Rock beer, the logo for which is a horse. 3. When Ralph is having sex with Tracee at the Bing, it is shot so that Ralph looks as though he is riding Tracee like a horse. 4. Ralph (disingenuously) suggests that he and Tracee could buy a house in Colts Neck, New Jersey. 5. Tony tells a stripper at the Bing that he wants to show her "where the horse bit" him, just before Tracee tries to get his attention. 6. Shortly before he kills Tracee, Ralph tells a joke about General Custer's defeat at the Battle of the Little Bighorn, where Custer's 7th Cavalry---a regiment of soldiers on horseback---was defeated by the plains Indians---also master horseback riders and led by the Indian chief Crazy Horse.
The horse-whore connection again presents itself in the plot involving Tony, Ralph, Valentina, and Pie-O-My. In the Season 4 episode "Mergers and Acquisitions," Tony meets Valentina---Ralph's "whore"---at the stables and, later, Valentina convinces Tony to have his horse, Pie-O-My, painted by an artist. Although Tony and Valentina eventually end up together, Tony is hesitant at first: He explains to Valentina that since he already took Ralph's horse, he can't have a relationship with her---i.e., he can't take Ralph's horse AND his "whore."
In the next episode, "Whoever Did This," Pie-O-My is badly burned in a fire and, while she actually survives, must be put down. In the Season 5 episode "The Test Dream," Valentina, once Ralph's and now Tony's "whore," is, like Pie-O-my, badly burned. And, like Pie-O-My, Valentina survives, but Tony has to "put her down" to move back in with Carmela---a point made clear in Tony's dream later in this episode. In the dream, Carmela tells Tony that he cannot bring his horse in the house because it defecates inside. Interpretation: If Tony is going to move back in with Carmela, he must keep his "whores" (and their crap) out of the home---in Season 4, Carmela finds Valentina's fake nail in the Sopranos' home, and Irina's phone call to the Sopranos' home results in Tony and Carmela's separation.
Note that there is a subtle cue in "Chasing It" to "Mergers and Acquisitions" and "The Test Dream." In "Chasing It," we see Little Vito step in his own feces; in "Mergers and Acquisitions," we see Ralph step in horse feces in the same graphic detail, and in "The Test Dream," Tony tells the valet at the Plaza to keep his car "out of the horse sh*t."
A few other examples of the horse-whore connection: 1. In the Season 2 episode "Knight in White Satin Armor," Irina tells Tony that she loves her "new pony boots." 2. In the Season 5 episode "Two Tonys," Tony, Feech, Chris, Sil, and Paulie are out to dinner with their "whores." Paulie exclaims "hold your horses" when his "whore" asks if they can go. 3. In the Season 5 episode "All Due Respect," Tony discovers that his painting of Pie-O-My is hanging in Paulie's condo. Tony asks Paulie if he and his "whores" get a big laugh out of it.
Finally, there is also a parallel between the death of Pie-O-My and the death of Renata. If you assume that Ralph killed Pie-O-My, it was over $200,000 in insurance benefits. If you assume that Tony killed Renata, it was over a $200,000 gambling debt.
d. Additional allusions to Godfather 1's horse-head scene
1. Tony, through his malapropism---"entrails" instead of "entails"---unwittingly references a slaughtered animal (4:09). 2. In the Season 4 episode "Everybody Hurts," A.J.'s friend jokes that Tony would put a horse's head in a senator's bed to ensure that A.J. didn't get drafted in to the army. In both "Everybody Hurts" and "Chasing It," the plot involves a loan between Tony and one of his non-mafia friends. Also, in "Chasing It," Carmela throws at Tony the Lladro that she (sort of) brags about in "Everybody Hurts." 3. "Chasing It" was written by Matthew Weiner. Weiner previously relied on the horse head to symbolize the menace of the Mafia in the Season 6 Part I episode "Luxury Lounge." In the scene in which Christopher and Little Carmine meet Ben Kingsley and Lauren Bacall, we see decorative posts lining the outdoor swimming pool. These posts are ornamented with horse heads, which serve as a sign of things to come: Christopher intimidating Ben Kingsley and punching Lauren Bacall in the face. 4. During "Chasing It," we see that Hesh keeps a glass of water and a black phone on his nightstand. In Godfather 1, we see that Woltz also keeps a glass of water and a black phone on his nightstand. 5. In the scene immediately preceding the one where Hesh finds Renata dead, Tony learns that he lost a bet on the Spurs/Mavericks game. A spur is of course used in horseback riding, and the Dallas Maverick's logo is a horse's head.
2. OTHER HINTS THAT TONY HAD RENATA KILLED
a. Allusions to the Season 1 episode "College"
There are (at least) two references in "Chasing It" to the Season 1 episode "College": 1. Marie Spatafore asks Tony for $100k to move to Orono, Maine, "by the University" (she's referring to the University of Maine). In "College", Tony took Meadow to look at schools in Maine. 2. Speaking with Dr. Melfi, Tony mocks Hesh's (purported) cheapness with a joke referencing a "Kruggerand." In "College", Meadow tells Tony she suspects he's in the Mafia after finding $50k worth of Kruggerands in the house while hunting for Easter eggs. These references to "College" are significant because "College" established that Tony is a killer (we see Tony strangle the rat living in hiding near Colby College---his first murder in the show).
b. References to boats
"Chasing It" contains multiple references to boats: Toward the beginning of the episode, Hesh laments to Renata about how much money Tony spent on his new boat; in the middle of the episode, Tony invites Hesh to a boat show; toward the end of the episode, Hesh jokes that it was him, not a fireboat, in the bathroom. These boat references hint at Tony's murderous past. In the Season 1 episode "I Dream of Jeannie Cusamano", Tony murders Chucky Signore on his motor boat. In the Season 2 episode "Funhouse", Tony of course kills Pussy on a boat. In the Season 6 Part II episode "Remember When", Tony contemplates killing Paulie on a boat.
c. Allusions to the Season 1 episode "Nobody Knows Anything"
There are allusions in "Chasing It" to the Season 1 episode "Nobody Knows Anything" (NKA). This is significant because in NKA, Sil and Tony joke that they would rather kill someone than pay off a $30k gambling debt (but are they joking?). The allusions to NKA in Chasing It: 1. In "Chasing It," Carmela tells Tony he goes about life as though there isn't a piano hanging over his head. In NKA, at the Sopranos' house party, Tony must move the family piano because AJ doesn't use it, and we see Tony move it in a scene shot directly from above; in the next scene, we see Tony tell Melfi that he feels as though there is a safe hanging over his head---a sense of "pending doom". 2. In "Chasing It," we see Tony get physical with Carmela, and she ends up throwing her prized Lladro at him; in NKA, Makazian tells Tony that when he was a kid, his dad would hit his mom and his mom would inevitably throw the closest thing she could find at him. 3. In Chasing It, we see Tony leave Carlo outside the pork store after an unexplained meeting---this scene is shot from across the street; in NKA, we see Paulie watching Pussy leave Tony, Chris, and Sil outside the pork store after an unexplained meeting---this scene is also shot from across the street. (Also, when Paulie pulls up to Pussy, he blows his horn, which plays the Godfather theme (see discussion of the Godfather 1 above)).
d. Noteworthy cuts
1. After Tony and Hesh's first awkward interaction regarding the $200k loan, the episode cuts to Hesh walking into his bedroom. We see a framed photo of Renata, prominently front and center in the shot, as he walks in. 2. After we see the Soprano family and Blanca eating dinner outside, the episode cuts to Carmela's parents asleep in bed. Carmela's mom is lying face up, looking like she could be dead. (This obviously doesn't suggest Tony had Renata killed, but it's an interesting cut because it presages the episode's ending.)
3. CIRCUMSTANTIAL EVIDENCE THAT TONY HAD RENATA KILLED
There is circumstantial evidence to support the idea that Tony had Renata killed. First, Tony knows Hesh's house well enough to give instructions; we've seen him there multiple times throughout the show. Second, we see that Hesh and Renata sleep with a glass of water next to their bed (13:17). This could be used for poisoning. Third, Tony just lost again on the Mavericks/Spurs game---he must be down BIG at this point---in the scene immediately preceding the one where Hesh finds Renata dead. Fourth, as Tony leaves Hesh's house at the end of the episode, the door doesn't shut properly, suggesting that it's not secure and that the house is easy to break into.
Finally, there is the unexplained scene in which Tony meets with Carlo in front of Satriale's (41:49), immediately after Tony loses $100k on the Eagles/Dolphins game. What were they discussing? One clue is that this scene is shot from an unusually low angle. This angle could suggest that this is a low moment for Tony---it certainly would be if he and Carlo were discussing killing Renata, who is completely innocent, over a valid debt to Hesh. The low angle could also serve to remind us that Tony is, in the words of Eric Scatino, a "real low-life." In the Season 2 episode "The Happy Wanderer," Eric loses his car because his father could not pay back his gambling debt to Tony.
4. SUMMING IT UP
Chasing It is littered with clues suggesting that Tony killed Renata. Now one may ask: Why would Tony kill Renata AND pay Hesh? It may have been a way for Tony to walk the line between meeting his obligations as a Mafia boss while also maintaining his violent reputation. Tony makes clear to Bobby and Carlo that he will look bad if he, as "head of the family," fails to pay back a debt. It would suggest to the outside world that Tony is an unreliable borrower that is having financial difficulties. But Tony is also well aware that he must be perceived as ruthless to maintain the respect of the violent criminals that comprise his crew (we saw in the Season 6 Part I episode "Mr. & Mrs. John Sacrimoni Request..." how quickly Tony could lose respect if perceived as weak). Tony asks Bobby and Carlo how it will look if he doesn't pay back Hesh. But how is it going to look to Bobby, Carlo, and the rest of the crew if Tony is brought to his knees financially by Hesh, an old man who is not a member of the Mafia? By paying back Hesh and killing Renata, he maintains his reputation as a reliable business partner AND a ruthless killer.
I think this explanation is the best one because it is consistent with all of the symbolism and allusions to past episodes that are discussed above. However, I don't claim that Tony DEFINITELY killed Renata. There are certainly alternative explanations. It could be that Tony attempted to kill Hesh, but accidentally killed Renata. Specifically, Tony could have sent someone to Hesh's house to poison him, but that Renata was poisoned instead---it's not far fetched that she would drink from the cup next to her and Hesh's bed. (Later in the same season, we see another botched murder attempt: Tony's crew ends up killing the innocent Ukrainians instead of Phil.) Renata may also have died from natural causes. This would certainly be in keeping with the themes of luck and fate that permeate the episode through its focus on gambling. In sum, I think the writers intentionally left this ambiguous. In NKA (a fitting title), we wonder: Is Pussy a rat? We don't know (at least not then). In "Whoever Did This" (another fitting title) we wonder: Did Ralph kill Pie-O-My? We don't know. In "Chasing It," we wonder: Was Renata's death random or planned? We don't know. And, of course in the last episode, we wonder: What happened to Tony? We don't know.
"Chasing It," with its use of symbols, allusions to past episodes, and an ambiguous ending, is so typical of David Chase that the title "Chasing It" is probably a reference to Chase himself. Toward the end of the episode, Tony speaks to Carmela about his gambling: "but you start chasing it. And every time you get your hands around it, you fall further backwards." This line may have a "meta" purpose: every time you think you have your hands around "meaning" in The Sopranos, you realize you don't---there may be a different meaning, or perhaps no meaning at all.
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