Day 75: Shadow Mentors

In the day 74 post, we looked at three characters from Treasure Island as luminary mentors to the protagonist, Jim Hawkins. Each of these mentors, Livesey, Smollett, and Trelawney, represent an aspect of Plato’s tripartite psyche, demonstrating rational judgment and ethics, courage and discipline, and desire and ambition respectively. The cast of characters also includes shadow mentors who have similar capacities but without the same moral constraints. They are Silver, Hands, and Gunn. 

Livesey/Silver

Livesey and Silver both possess the ability to keep cool and listen, which reveals their rational natures, but they have very different worldviews as revealed through their treatment of others. The two perspectives show Jim and the reader two ways of applying reason to human relationships: preserving dignity versus reducing people to instrumental good. 

Livesey values Jim's intelligence and observation while guiding him toward ethical behavior. He encourages and nurtures Jim for his own good. He shows Jim his belief in the inherent worth of humans by treating the sick and injured pirates as patients. 

Silver recognizes Jim's potential while trying to corrupt him toward pragmatic amorality. Instead of empowering Jim, Silver grooms him as a potential ally while being willing to sacrifice him. He treats potential allies as disposable tools.

From these mentors Jim learns observation and strategic thinking with two distinct types of leadership: ethical versus manipulative. Ultimately, Jim chooses Livesey’s path of using his wits for the good of others. Even in his most Silver-like moments when Jim makes autonomous decisions, he ultimately serves the innocent crew members. 

Smollett/Hands

Smollett and Hands both possess strong attitudes about authority, but they employ different means to secure their power over others and have different sources. This can be seen in their approach to discipline. 

Smollett maintains strict control through abstinence and military routine. His displeasure with Jim’s behavior isn’t personal but a concern about the disruption to the proper hierarchy and the dereliction of duty. Smollett represents legitimate authority based on principles. Hands enforces control through indulgence paired with physical violence and resents any challenge to his authority as a personal challenge. Hands favors raw power based on physical domination. 

By observing Smollett and Hands, Jim experiences two forms of authority: principled discipline that protects and brutal force that dominates. Through their dislike of Jim, each pushes him to prove himself. He wants to show Smollett that he can act responsibly, and he meets Hands’s physical violence with moral courage. In his fight with Hands to keep control of the Hispaniola, Jim employs physical courage like the pirate in service of a righteous cause like Smollett.

Trelawney/Gunn

Trelawney and Gunn both demonstrate an appetite for adventure, which makes them ambitious. They can convert this energy into action taking them closer to what they desire. Trelawney shows the ability to move toward productive action that enables him to defend his friends. Unlike Gunn, who spends his entire share of the treasure within nineteen days of returning to England, Trelawney successfully integrates his appetites with social responsibility. In this way, he goes from being a liability (getting duped by Silver at the outset) to being an asset through the disciplined use of his natural gifts (applying his marksman skills to enable the innocent crew members to escape the Hispaniola). Gunn fails to be transformed by his experience. His years stranded on the island without human connection have put this possible development out of reach. 

From the examples set by these two mentors, Jim can see two paths for adventure-seeking including Trelawney’s evolution toward channeled enthusiasm for the good of others and Gunn’s cautionary tale of unintegrated desires. In the beginning, Jim is drawn to pure adventure, like these two mentors, but he learns to balance adventure with responsibility. The treasure itself is the ultimate test. Like Trelawney, Jim learns to use the power of wealth responsibly and shows no interest in pursuing more treasure by adventure. 

Jim’s Education

These patterns suggest that each luminary-shadow mentor pair demonstrates not just qualities (reason, spirit, ambition) but how those qualities interact with power, authority, relationships, and human development. Jim (and readers) gain a complex education in how character shapes the use of power and influence through the clear consequences of each approach. Jim's journey can be seen as navigating between these paired approaches to power, authority, and morality, learning from both the luminaries and shadows before integrating the lessons into his own character.

By the end, Jim has developed reason that serves moral ends (Livesey/Silver), learned courage that upholds principles (Smollett/Hands), and channeled his appetites toward productive ends (Trelawney/Gunn).

What's particularly elegant is how Jim doesn't simply choose the "good" mentors over the "bad," he learns skills and capacities from both sides but integrates the lessons in a moral direction.


This post is the final of my 75-day writing challenge and experiment. Every day since September 9, I’ve posted daily thoughts on writing, storytelling, and creativity based on recent readings or reflections. My goal was to explore and share short posts with value for writers. Now that the challenge is over, I will reflect on the experiment and decide what to do next. As part of that process, I’ll organize and revise the material with intention. 

If you  have questions about anything I’ve shared in these posts, please feel free to write to me: leslie@writership.com.