It is against a remarkable backdrop of complicated wooden sailing ships and their overwhelmingly complex management and warfare that we may see true leadership displayed in ways most interesting and instructive. Given the challenges of these massive sailing cities from operational, tactical, and strategic considerations, the need for leadership in this historic era was monumental. It is when challenges are the greatest, when pressures are the highest, when risk is at its maximum, that the real mettle of leaders is revealed. Leaders who could rise above such demanding circumstances as those in the age of fighting sail are truly worthy of study. In their time, so foreign from ours, in how they did what they did, and why, there is much for today’s leaders to learn.