Beyond Either/Or: The Practice of Complexity
A Monthly Series
Issue 2 • August 2026

When I teach about Velupillai Prabhakaran, the leader of the Liberation Tigers of Tamil Eelam, an organization I studied for my doctoral dissertation, I present a complex profile of a complicated individual. There was this man who built and led a large organization, commanded a substantial following, and successfully advanced many of the organization’s goals over several decades. A famously elusive figure, Prabhakaran interacted with very few reporters, making their accounts an important source for understanding a leader who was unquestionably a great military strategist. Accounts of his leadership also describe him as disciplined, brave, committed, and charismatic. LTTE supporters whom I interviewed described him as honest, compassionate, and driven by a sense of justice. To them, he was an ethical decision maker, an older brother, a supporter and protector, and ultimately a savior of the Tamil cause.

Then we confront more facts. Prabhakaran led an armed organization. The LTTE was responsible for acts of violence that caused immense suffering, including among the people it claimed to represent. The final years of the conflict produced grave violations and enormous suffering, with abuses attributed to both the LTTE and the Sri Lankan government. Prabhakaran died a gory death at the hands of the Sri Lankan military, betrayed by some of his own men.

Holding these realities together generates some of the richest conversations in the class. Can someone possess qualities associated with strong leadership while making decisions that cause others harm? Can a leader be kind and compassionate toward some and ruthless toward others? Is effective leadership more or less important than the moral consequences of that leadership?

These conversations are not only about Prabhakaran. They expose the inadequacy of the categories we use to understand leaders. We have taught ourselves to see them as good or bad, and we do not always know how to speak about them when their story does not neatly fit either category.

Why We Need the Categories

We often understand a leader through stories. We build those stories from an individual’s history, attitudes and behaviors, strategies and actions, morals and values. And no matter how complex those stories are, we strive to simplify them. We rely on simple categories, such as asking whether “our” leader is a hero or a villain.

Those categories do more than tell us who the leader is. They tell us what our relationship with that leader should be. The hero is someone to admire, support, and perhaps defend. The villain is someone to condemn, resist, and perhaps defeat.

We expect a great deal from those who lead us. The leader is expected to somehow rise above being human. Personality flaws become leadership flaws, errors in judgment become evidence of bad leadership, and failures of values or morals can come to define the leader altogether. An enormous amount is written about what makes a good or effective leader.

The halo effect helps further explain some of this. One positive impression can color how we see other qualities in a person, while a negative impression can work in the opposite direction. Once a leader becomes a hero, compromise becomes pragmatism, aggressiveness becomes conviction, and harm becomes the collateral damage of pursuing a larger goal. Once the leader becomes a villain, pragmatism becomes opportunism, conviction becomes fanaticism, and success becomes luck or manipulation. It is easier to make someone coherent than to hold contradictory qualities together.

When the leader becomes the villain, it becomes easy to place ourselves in the “other” category. They are the leaders; we are the people being led. They are the problem; we are the people harmed by, resisting, or seeing through the problem. If the problem resides in them, the solution seems equally obvious: bring them down. The hero creates another version of the same binary. The hero becomes one of us, perhaps even the embodiment of who we believe ourselves to be. Criticism of the leader can feel like criticism of our group, our values, or our own judgment. Defending the leader becomes entangled with defending ourselves.

Hero and villain, then, do not simply create categories for leaders. They create categories for the rest of us. Once again, we find ourselves choosing sides: us and them. Judging the leader then becomes the primary task of anyone who occupies the position of follower, subject, direct report, or member of a community. Given the illusion of moral superiority, we invariably come off looking better than the leader. The leader’s moral shortcomings are visible. Ours are safely outside the frame.

The categories of heroes and villains do not simply reassure us about who the leader is. They can reassure us about who we are.

What the Categories Allow Us Not to See

We tend to pay much less attention to ourselves — to those of us who are not the leaders. The article “In Praise of Followers” points out that our preoccupation with finding better leaders can cause us to lose sight of the people they lead. We should not forget that leaders and followers influence each other.

As followers, we are not neutral observers of leadership. We bring our personalities, histories, expectations, biases, loyalties, interests, values, and flaws into the relationship. We can support, challenge, resist, enable, idealize, or undermine. We can demand things of leaders that we would struggle to do ourselves. We can also overlook behavior in a leader we admire that we would immediately notice in one we dislike. Followers are no less human, and therefore no less flawed, than leaders. That does not mean we carry equal responsibility. Power matters, and those with greater power must be held to greater account. But unequal responsibility does not mean that only one side of the relationship deserves examination.

The hero-villain categories make that examination particularly difficult. If the leader is the villain, the questions are all directed outward: What is wrong with them? Why did they make that decision? Why are they behaving this way? How do we stop them? If the leader is the hero, we may ask even fewer questions. What we are less likely to ask in both contexts is: What am I bringing into this relationship? What have I enabled, excused, resisted, or misunderstood? Have my expectations of this leader been reasonable? Would I interpret the same behavior differently in someone I had already placed in the other category?

Perhaps this is one of the most consequential things our categories allow us not to see: ourselves.

Beyond Hero and Villain

We should not stop judging leaders, especially those we elect or hire into positions of power. Judgment matters. Accountability matters. Moving beyond binary thinking does not require neutrality or pretending every action is equally defensible. What we need to do is to resist taking the shortcut from judging an action to judging an entire person. We need to resist the comfort of believing that because the leader is the one being judged, there is nothing about ourselves worth examining.

When I return to Prabhakaran in the classroom, perhaps the point is not to decide whether he was a hero or a villain. It is to notice how urgently we want to decide.

So here is the practice I am trying to build into my own thinking. When I find myself looking for hero or villain, I pause and ask: What would I have to leave out of this story to make that label fit? If I have strong feelings about this leader, what am I finding difficult to see? And perhaps there is one more question: What am I finding difficult to see about myself?

The answers may not change whether I support or oppose the leader. That is not the purpose. The purpose is to make sure that the category has not done the thinking for me.

That is the beginning of the practice of complexity.

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