Claim: Out of all the Scottish League Cup winning managers, Walter Smith, Jock Stein, and Scot Symon each won six, tying for the most wins.
Evidence: Scot Symon, Jock Stein and Walter Smith are the most successful managers in the history of the competition, having each won 6 Scottish League Cups during their careers. 
Walter Smith (6) Jock Stein (6) Scot Symon (6)