"Chasing It" is the 4th episode of Part 2 and the 16th overall episode of Season 6 of the HBO original series The Sopranos. It is the 81st overall episode of the series. Written by Matthew Wiener and directed by Tim Van Patten, it originally aired on April 29, 2007.
- James Gandolfini as Tony Soprano
- Lorraine Bracco as Dr. Jennifer Melfi
- Edie Falco as Carmela Soprano
- Michael Imperioli as Christopher Moltisanti
- Dominic Chianese as Corrado Soprano, Jr. *
- Steven Van Zandt as Silvio Dante
- Tony Sirico as Paulie Gualtieri
- Robert Iler as Anthony Soprano, Jr.
- Jamie-Lynn Sigler as Meadow Soprano
- Aida Turturro as Janice Soprano Baccalieri *
- Steven R. Schirripa as Bobby Baccalieri
- Frank Vincent as Phil Leotardo
- Dan Grimaldi as Patsy Parisi
- Max Casella as Benny Fazio
* = credit only
- Jerry Adler as Hesh Rabkin
Also guest starring
- Nancy Sinatra as Herself
- Tom Aldredge as Hugh De Angelis
- Elizabeth Bracco as Marie Spatafore
- Arthur J. Nascarella as Carlo Gervasi
- Dania Ramirez as Blanca Selgado
- Suzanne Shepherd as Mary De Angelis
- Brandon Hannan as Vito Spatafore, Jr.
- Anthony J. Ribustello as Dante Greco
- Taleb Adlah as Ahmed
- Donnie Keshawarz as Muhammad
- John "Cha Cha" Ciarcia as Albie Cianflone
- Matthew Del Negro as Brian Cammarata
- Paulina Gerzon as Francesca Spatafore
- Geoffrey Cantor as Eli Kaplan
- Tracey Silver as Beth Kaplan
- Lanette Ware as Renata
- Joseph Perrino as Jason Gervasi
- John Cenatiempo as Anthony Maffei
- Mason Pettit as Ted Yacanelli
- Drew Wininger as Fan
- Kobi and Kadin George as Hector Selgado
- Heidi Dippold as Janine Cammarata
- Southside Johnny as Himself
Tony hits a particularly unlucky gambling stretch and his losses begin to impact his financial obligations as boss of the Soprano crime family. Vito's widow, Marie, asks Tony for help regarding her son Vito Jr., who has become antisocial following his father's murder. Marie also requests $100,000 to move her family to Maine to start over. Tony resists and suggests that Phil, who killed Vito, should get involved. Phil agrees to talk to Vito's son. Both men each talk to Vito Jr. to try to make him stop his delinquency, but their attempts fail. Neither of them are willing to fund the Spatafore family's move to Maine.
After Vito Jr. is expelled for defecating in the school shower, Tony changes his mind and says he will pay for the Spatafores' relocation. He angrily adds he will "never forgive" Phil for not coming through on the financing for the family's move. However, Tony soon gambles away the $100,000 he had reserved for the Spatafores on a football bet. In a change of plans, he offers Marie to pay her to sign Vito Jr. up to a boot camp program in Idaho instead. He plays down Marie's worries that corporal punishment is permitted in such places, assuring her not to "worry" about the expenses as he will pay the $18,000 for it. Reluctantly, Marie accepts. Vito Jr. is taken away from his home against his will by the boot camp's representatives, leaving his mother and sister in tears at the sight.
Hesh begins to regret lending $200,000 to Tony as a bridge loan. Tony only grudgingly pays Hesh his points, often making a show of the act. Hesh, suffering from hypertension, becomes concerned that Tony will kill him rather than pay and reflects that debts end up destroying friendships. Bobby and Carlo encourage Tony to stiff Hesh, but Tony angrily rebukes the idea. Later, Tony notices Ahmed and Muhammad mingling with traditionally dressed Middle-Easterners on a street. Meanwhile, A.J. proposes to Blanca, who initially accepts but later ends the relationship during the Puerto Rican Day Parade, citing her uncertainty over whether she loves him.
Carmela and her father Hugh sell their spec house to her cousin Brian Cammarata. Carmela worries about the sub-standard building materials Hugh used, but he says he has used the same material before. When she tells Tony that she has cleared $600,000 on the house, he informs her about a "sure thing" gambling tip and encourages her to bet some of "his half" on a football game. When Carmela refuses, Tony initially accepts. However, when Tony's pegged team wins the game, he becomes furious that Carmela kept him from winning big. They get into a heated argument in which Tony brings up Carmela's previous theft of his money and reminds her that he made the building inspector ignore the construction shortcomings. Carmela storms off when Tony implicitly threatens that the house's roof will collapse and kill Brian's unborn child.
In a session with Dr. Melfi, she confronts Tony about his habit of selectively attending their meetings, telling him to either participate in therapy diligently or quit. Tony assures her he will attend the sessions. On the subject of his gambling fever, Melfi questions Tony if what he is "chasing" is really the money or the "high from winning." Tony admits there would be no attraction to gamble if the practice did not carry the inherent danger of losing. Tony and Carmela reconcile, and she expresses fear that their family is constantly vulnerable to various threats. Tony says that, despite his gambling losses, he survived getting shot and therefore, in the bigger picture, is "up" in life. After Hesh's girlfriend suddenly dies of an apparent stroke, Tony finally brings the full sum of owed money to a distraught Hesh and expresses his condolences.