6. Tony: The Gambler
Episode Title: "Chasing It" (Season 6, Episode 16)
Is this really the best they could do? As the series raced to its conclusion (there were just five episodes left) and the war between the Soprano and Lupertazzi crime families was at its boiling point, Tony suddenly becomes a degenerate gambler who's in debt to longtime family friend Hesh Rabkin for $200,000? The whole plotline seemed contrived for the sole purpose of taking Hesh (well played by Jerry Adler) off the call sheet for the duration of production.