It — [s6e16] Chasing

The narrative follows several threads of "unfortunate sons" and strained fatherly relationships:

: The relationship between Tony and Hesh shifts from friendship to a tense creditor-debtor dynamic. Tony serves up anti-Semitic remarks alongside his weekly interest payments (vig), leading Hesh to fear that Tony might kill him to clear the debt. [S6E16] Chasing It

: Tony finds himself in a severe gambling slump, losing heavily on sports bets and at the casino. His behavior becomes increasingly reckless and petty, particularly in his treatment of his long-time advisor Hesh Rabkin , from whom he has borrowed $200,000. The narrative follows several threads of "unfortunate sons"

: AJ proposes to Blanca, but she breaks off the engagement shortly after, sending him into a deep depression that marks his arc for the remainder of the season. Critical Analysis: "Chasing It" Tony's "solution" is to send him to an

: Marie Spatafore's son, traumatized by his father's death, begins dressing "goth" and acting out. Tony's "solution" is to send him to an abusive boot camp rather than funding the family's relocation to Maine, largely because he had gambled away the potential funds.

Critics and fans often debate the "out-of-nowhere" nature of Tony's gambling addiction in this episode: