The Sopranos: Season 6, Episode 16

6 - 16: Chasing It

At the Borgata Casino, Tony decides to let it ride after winning at roulette. Tony loses everything he'd won, and then some, on 23. Meanwhile, Vito Jr. is going through a rebellious phase. Tony asks Phil to talk to Vito Jr. Phil grudgingly agrees. AJ proposes to Blanca over a nice dinner, promising her that he will rise from pizzeria night manager to restaurant chain owner in no time, and coaxes a "yes" out of her. At the Puerto Rican day parade, Blanca meets up with AJ and returns his engagement ring, telling him she just doesn't feel it.