Chuck Rhoades, Sr.

Chuck Rhoades, Sr. is old New York money — a real-estate power broker who has spent decades trading favors, memberships, and quiet threats in rooms his son is still trying to enter. He dotes on Chuck Jr. with genuine affection, then undercuts him with lessons in leverage disguised as fatherly wisdom, treating ambition as the family religion.

DeMunn plays him with a courtly, unhurried menace, all soft voice and steel underneath, so every piece of advice sounds like love until you notice what it costs. He's the show's clearest argument that its hero's hunger for power was inherited, not chosen — a father who made corruption look like tenderness.