Sherbrooke as a model for aggressive destroyer raiding

Which late-1930s Royal Navy captain would suit a raiding role against Spanish treasure traffic?

Robert Sherbrooke is his preferred example, with Tribal-class senior officers generally well suited to the aggressive role.

Robert Sherbrooke is a stronger fit than Philip Vian for the imagined raiding role. The joking description of Sherbrooke as the more piratical figure matches the premise of attacking Spanish treasure traffic. Senior officers associated with the Tribal-class destroyer force also had the experience and temperament for such a mission. The playful scenario points toward Royal Navy destroyer leadership in the late 1930s.