Every time he commits adultery, kills someone, or mouths off to his kids.
So, in short: Tony Soprano is ruthless with EVERY moment in EVERY scene in EVERY episode. There is not a moment where he isn't ruthless.
Mick
...dot com bold typeface rhetoric. You go clickety click and get your head split. 'The hell you look like on a message board Discussing whether or not the Brother is hardcore?