Chasing It (S06E16)
Airdate: April 29th 2007
Written by: Matthew Weiner
Directed by: Tim Van Patten
Running Time: 50 minutes
As The Sopranos edged towards its enigmatic conclusion, the spectre of closure loomed large. With only a handful of episodes remaining, the series’ narrative economy demanded that certain characters be ushered unceremoniously offstage. In Chasing It, the episode of second part of Season 6, that character is Hesh Rabkin—Tony Soprano’s long-time confidant and occasional creditor. His exit, while telegraphed in prior instalments, epitomises the episode’s broader shortcomings: a reliance on contrived plot devices and a jarring departure from the show’s signature psychological nuance. What could have been a poignant exploration of loyalty and decay instead becomes a muddled exercise in ticking boxes before the finale.
Hesh’s departure had been signposted in Remember When, where Tony’s spiralling gambling debts first strained their relationship. Chasing It amplifies this tension, framing Hesh not as a casualty of mob violence, but of Tony’s self-inflicted financial ruin. The episode leans heavily into Tony’s sudden, poorly established gambling addiction—a narrative choice that feels less like organic character development and more like a blunt instrument to sever ties with Hesh. Tony’s mounting losses, depicted through a cliché-ridden losing streak (failed sports bets, a botched roulette spin), strain credulity. While James Gandolfini’s performance simmers with volatile charm, the script reduces Tony’s complexity to that of a petulant addict, his actions dictated by plot necessity rather than inner turmoil.
Carmela’s subplot offers fleeting respite from Tony’s decline. Her successful sale of a speculative property—a hard-won victory in her quest for financial autonomy—should symbolise her evolution beyond Tony’s orbit. Instead, it becomes a catalyst for his resentment. Tony’s demand that she invest her profits into his doomed bets lays bare his toxic entitlement, while her refusal sparks a marital rift that culminates in a chilling confrontation. Edie Falco and Gandolfini excel in these scenes, their chemistry veering from tenderness to contempt. Yet their reconciliation—a fleeting truce—feels unearned, a narrative reprieve that undercuts the episode’s darker themes.
The episode’s most damning indictment of Tony comes via his handling of Vito Spatafore Jr.’s plight. Grieving his father’s murder, Vito Jr. (a wooden Brandon Hanan) adopts gothic theatrics and vandalises a grave. His mother Marie (Elizabeth Bracco, underused) pleads for $100,000 to relocate the family to Maine—a request Tony initially entertains. However, his gambling losses prompt a callous pivot: he opts for a cheaper “boot camp” solution, outsourcing the boy’s trauma to strangers. This subplot, intended to showcase Tony’s moral decay, instead drowns in melodrama. A gratuitous scene of Vito Jr. defecating in a shower plays like edgelord provocation, undermining any empathy for his character. The arc’s resolution—a hasty dispatch to Idaho—feels less like tragedy than narrative housekeeping.
Hesh’s farewell epitomises the episode’s narrative laziness. His growing unease over Tony’s debt—a legitimate fear, given mob precedent—is abruptly sidelined by the sudden death of his girlfriend, Renata (Lanette Ware). Her fatal stroke, while emotionally resonant for Hesh, reeks of contrivance, a cheap device to expedite his exit. When Tony coldly settles the debt at her funeral, their fractured friendship is reduced to a financial transaction. The moment should resonate as a quiet tragedy; instead, it lands with a shrug, emblematic of the episode’s indifference to its own characters.
A.J.’s romantic misadventures, meanwhile, epitomise the episode’s haphazard pacing. His promotion at pizzeria and proposal to Blanca (Julissa Lopez) hint at maturity, but her abrupt rejection—explained vaguely as a mismatch in life goals—feels unanchored. The subplot, while reflective of A.J.’s perennial arrested development, lacks the emotional heft of prior arcs, rendering it a footnote rather than a meaningful thread.
Written by Matthew Weiner, Chasing It suffers from uncharacteristic tonal whiplash. Tony’s gambling addiction, introduced with minimal setup, relies on hackneyed tropes: the “sure thing” bet gone wrong, the desperate chase for losses. The episode’s title, a gambling term, becomes a heavy-handed metaphor for Tony’s recklessness, but the parallels feel forced. Even Weiner’s avoidance of violence in Hesh’s exit—a commendable subversion of mob tropes—rings hollow, as Renata’s death substitutes one contrivance for another.
The Vito Jr. subplot, with its mix of bathos and shock value, further highlights Weiner’s misjudgement. The shower defecation scene, aiming for dark comedy, instead plays as crass and exploitative—a nadir for a series once celebrated for its subtlety.
Amid the dross, Nancy Sinatra’s cameo as herself at Phil Leotardo’s victory dinner offers a glimmer of levity. Her rendition of Big Boss Man—a cheeky nod to mob violence—infuses the episode with surreal glamour. Yet this moment, while memorable, feels tonally adrift, a self-aware gag in an otherwise dour hour.
Chasing It stands as one of The Sopranos’ lesser entries, a victim of its rushed endgame and narrative shortcuts. While it sporadically channels the series’ genius—particularly in Carmela’s resilience and Hesh’s dignified despair—its reliance on clichés and contrivances undermines its ambitions. Hesh’s exit, though inevitable, encapsulates the episode’s failings: a character of depth reduced to a narrative inconvenience, dispatched not with pathos, but procedural haste. In a series renowned for its moral complexity and psychological rigour, Chasing It feels like a placeholder—a stumbling block on the road to greatness, rather than greatness itself.
RATING: 5/10 (++)
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