Black Sails

Lessons in Leadership from the Pirates of Nassau

Black Sails ended its third season last weekend. The series combines the characters of Robert Louis Stevenson’s Treasure Island with the historic figures of the golden age of piracy. The story serves as a prequel to Stevenson’s book and a fictionalized tale of the origins of Nassau.

The series is packed with action, adventure, and intrigue. It has a host of entertaining characters and plot twists. But among the many facets of its storyline is a central theme — leadership.

John Silver

From the very first episode John Silver has been an opportunist. Long before he exhibited any other character of leadership, he showed an innate talent for seizing an opportunity.

If you don’t consider this an attribute of a great leader, you haven’t been paying attention to the storyline. While a nose for opportunity is not sufficient to be a leader, it is an attribute that can really come in handy.

John adds another quite strong asset to his nose for opportunity. He is a people person. And while some of that comes in the form of a silver tongue, the majority is displayed by his concern for his crew.

This attribute is probably of greater importance. Great leaders are more often than not great with people. Respect, empathy, compassion, and communication are all hallmarks of great people leaders.

Charles Vane

If the phrase ‘follow the leader’ has a poster child it is Charles Vane. This rugged individualist is the antithesis of John Silver. People don’t follow Charles for his sense of empathy or compassion. They follow him because he leads by example.

Charles walks the walk and talks the talk. His character is strong, honest, and a role model to his men. He sets an example of courage, an example of sacrifice, and most of all an example of will.

He is also an example of freedom and individuality. Much like opportunity, these attributes may not strike you as essential to great leaders. Once again, they are hardly sufficient. But, they are incredibly important.

Freedom and individuality are a source of strength. These attributes are contagious. And as Vane demonstrates, they are a handy theme for a speech:

These men who brought me here today do not fear me, they brought me here today because they fear you. Because they know that my voice, a voice that refuses to be enslaved, once lived in you and may yet still. They brought me here today to show you death and use it to frighten you into ignoring that voice. But know this, we are many, they are few. To fear death is a choice, and they can’t hang us all…

Captain Flint

No leader ever used fear to such an advantage as Captain Flint. This may strike you as another unusual attribute for leadership, but the history of piracy is one that stands in stark contrast to that thinking.

Fear is motivational. Fear can strengthen respect though it is no substitute. Fear can create urgency and, as the pirates showed, can even prevent undo conflict.

If Flint is the master of fear, his grasp of commitment is beyond comprehension. His commitment has crossed oceans, led men to battle, and brought empires to their knees. When all hope is lost, Flint’s commitment only intensifies. For his men, this is a source of hope, strength, and comfort.

Eleanor Guthrie

Ms. Guthrie’s storyline is a compelling one. Many fans love her character, many more hate her. While her character is torn between numerous alliances, her leadership ability is equally tested by two separate burdens.

At the start of the series, Eleanor’s biggest struggle is with dependency. Instinct tells us that dependency is a thing to be overcome, but Eleanor’s story offers a different view. She is able to transform dependent relationships into alliances and partnerships, weakness into strength.

As her character’s confidence and power grow, as she assumes the mantle as leader of Nassau, Eleanor confronts the burden of authority. Authority is synonymous with leadership, but Black Sails does a tremendous job diving into the heavier side.

Eleanor battles with the weight of responsibility and the implications of her decisions. She is forced to make difficult choices in nearly every episode. She must choose between the people she loves and those she feels compelled to protect.

Jack Rackham, Anne Bonny, and Max

This trio shares quite a few bonds that aren’t limited to themes of leadership. Each character comes from humble beginnings and each has an incredible sense of ambition.

Ambition is a powerful source of energy and drive. It is an important asset of any leader when tempered. It drives great leaders to reach further, strive harder and attempt goals they might otherwise not. Ambition can be powerful and dangerous.

All three characters routinely dance on that edge. They do not possess the individual talents of many of the other characters. What they lack as individuals, they make up for with their intense loyalty. Loyalty makes a perfect attribute of leadership and a great way to end our article.

Loyalty is an attribute that provides leaders with immense leverage. Loyal teams push harder and are more likely to succeed. Loyalty makes a team more willing to look past shortfalls and mistakes. Just be careful. As our trio has also shown, loyalty lost is also a dangerous thing…