Part 5 of 13 in the Black Sails: A Leadership Masterclass series.

There's no such thing as halfway crooks.

You're in or you're out. You do the dirt or you don't. You can't stand with killers and keep your hands clean. You can't eat the sausage while flinching from the factory floor.

Billy Bones spends four seasons trying. He knows how the ship works. He runs the operations. He manages the crew and balances the books and keeps everything functional. He's competent, brave, loyal—genuinely good at his job.

But he can't stomach what the captain does to keep it running.

So he stays close enough to benefit and far enough to disapprove. He takes the prize shares while judging how they were won. He lives on the decisions he refuses to make.

This is the middle manager position. The director who sees the C-suite up close. The VP who knows where the bodies are buried but didn't dig the holes.

Scared to death. Scared to look.

Here's Billy's problem: he has two legitimate options.

Option one: Accept it. The ship runs on lies because truth wouldn't work. Men get sacrificed because missions require sacrifice. Flint does what captains do. If you want the benefits of piracy, you accept the costs of piracy. This is how it works. Stop complaining.

Option two: Oppose it. If Flint's methods are unacceptable, remove Flint. Take responsibility yourself. Build something different. Do it your way—and bear the weight of what "your way" actually requires.

Billy keeps choosing option three: witness and resent. Stay close enough to benefit. Complain about the methods. Never take the burden himself.

This is the halfway crook position. You get the profits while maintaining the posture of disapproval. You're complicit but not responsible. You're in but you keep telling yourself you're different.

The lie is that this is a stable position. It isn't. The world eventually forces the choice.

Watch Billy's psychology: he needs to believe he's better than Flint. Morally superior. The good man in a bad situation. This self-image requires maintaining distance from Flint's methods while benefiting from their outcomes.

But maintaining this distance is exhausting. Every decision Flint makes forces Billy to either endorse it or oppose it. Endorsing feels like complicity. Opposing risks everything. So Billy does neither—and does both. He goes along while making his disapproval clear. He benefits while signaling reluctance.

This is performance for an audience of one: himself. Billy needs to believe he's not like Flint. The performance convinces no one else. Flint sees through it. The crew sees through it. Everyone knows Billy is eating the sausage. Billy is the only one pretending the factory floor is someone else's responsibility.

The cognitive dissonance compounds. The more Billy benefits, the more he needs to disapprove to maintain his self-image. The more he disapproves, the more resentful he becomes. The resentment poisons everything—his relationships, his judgment, his capacity to lead when leadership is finally required.

What Billy can't see is that silence is also a choice.

When Flint lies to the crew, Billy knows it's manipulation. He's disturbed by it. He thinks the men deserve the truth.

But Billy doesn't tell them the truth. Because if he did, they'd lose the mission. They'd fall apart. They'd abandon the project Billy also wants to succeed.

So Billy stays silent. Benefits from Flint's lies while resenting them. Doesn't stop them but doesn't do them himself.

Except that's doing them. Benefiting from lies you don't stop is participating in lies. The clean hands Billy's protecting are already dirty. He just hasn't admitted it to himself.

Same with sacrifice. When the mission requires losing men, Flint loses them. It costs him—you can see it costing him—but he does it. Because someone has to make that call.

Billy won't make the call. Won't bear the weight. Thinks the willingness to make it is the problem, rather than the necessity.

But Billy keeps getting the benefits of decisions that required sacrifice. He's alive because Flint made calls Billy wouldn't make. His position exists because Flint absorbed costs Billy refused to pay.

Halfway.

This is the moral hazard of middle management. You're close enough to see the compromises. Far enough to avoid making them. You benefit from outcomes you didn't choose, but you tell yourself the choosing absolves you. The decider bears the moral weight; you're just following orders.

Except you're not just following orders. You're choosing to stay. Choosing to benefit. Choosing silence when you could speak. These are choices. The fact that they're passive doesn't make them less real.

Billy wants the comfort of powerlessness—wants to claim he couldn't have stopped Flint—while maintaining the authority of judgment. Can't have both. If you're powerless, you can't judge. If you can judge, you had power. Either you could have stopped him and didn't, or you couldn't have stopped him and your judgment is irrelevant.

Billy tries to occupy both positions. It eats him alive.

Mr. Gates shows the trap in its purest form.

Gates is the actual quartermaster in Season 1. Competent. Respected. A voice of reason in Flint's more extreme moments. He keeps trying to moderate Flint—pull him back from the edge, make the operation cleaner, safer, more sustainable.

This is good instinct. This is what good managers do. But Gates is trying to run a pirate ship.

Pirate ships run on extreme behavior. The edge is where the prizes are. Reasonable captains don't survive because unreasonable ones out-compete them. The moderation Gates keeps pushing would make the Walrus worse, not better.

When it finally comes to the choice—support Flint's extreme plan or oppose it—Gates opposes.

Flint kills him.

Not out of cruelty. Out of necessity. Gates became an obstacle. The mission can't carry obstacles. His halfway position—close to power but unwilling to embrace what power requires—made him expendable the moment he stopped being useful.

Every organization has Billy and Gates.

The operations people who understand how everything works. The middle managers who keep things running. The competent professionals who see leadership up close.

They often think they could do it better. More ethically. More sustainably. More fairly.

What they often don't see: they're benefiting from the decisions they criticize. The hard calls that keep them fed. The ruthlessness that maintains their position. The lies that keep the crew rowing.

This is the MBA trap. You learn enough to understand the machine but not enough to understand what running it costs. You watch the sausage being made and think you'd do it differently—while eating the sausage every day for lunch.

Maybe you would do it differently. But different has costs too. Different might not work. The things that bother you might be the things that make it work.

Billy eventually gets his chance. He rises to power in Season 4. Tries to do it his way. His way produces chaos, betrayal, collapse. Turns out Flint's methods weren't arbitrary. They were load-bearing.

This is the lesson Billy learns too late: the methods he hated weren't Flint's personality flaws. They were adaptations to constraints Billy never fully understood. Flint lied because truth wouldn't hold the crew together. Flint sacrificed because missions required sacrifice. Flint was ruthless because the situation punished hesitation.

When Billy is in the captain's position, he faces the same constraints. He tries to maintain moral purity while leading men in lethal situations. It doesn't work. The men need lies to stay motivated. The mission requires sacrifice. The situation demands ruthlessness.

Billy either becomes what he hated—adopts Flint's methods, proves they were situational rather than personal—or he fails. He chooses to fail. Can't stomach crossing the line he spent years criticizing Flint for crossing. His integrity stays intact. His leadership collapses.

The show doesn't tell you which choice was right. It shows you the trade-off. Effectiveness costs integrity. Integrity costs effectiveness. Billy chose integrity. Flint chose effectiveness. Both paid prices. Neither escaped unscathed.

The halfway crook is scared of both options.

Scared to fully commit. If you go all the way in, you become the thing you judge. You're the one lying, sacrificing, doing the dirt. Your hands get dirty. Your soul gets dirty. You lose the clean self-image that's been sustaining you.

Scared to fully leave. If you walk away, you lose the position. Lose the benefits. Lose the identity. Lose the thing you've built your life around.

So you stay in the middle. Keep one foot out. Maintain the posture of disapproval while accepting the check. Tell yourself you're different while doing the same job.

Billy does this for four seasons. Disturbed. Resentful. Plotting alternatives. But staying. Benefiting. Being complicit while feeling separate.

It doesn't hold. The world eventually demands you choose. And the longer you delay, the worse your options get.

Can you be a functional pirate with clean hands?

No.

Can you be close to power without sharing in its costs?

No.

Can you benefit from hard calls without being willing to make them?

No.

The halfway position is comfortable—for a while. But it has a shelf life. Eventually the operation needs you to commit or leave. Eventually the people making hard calls notice you're getting benefits without sharing burdens.

Billy and the quartermasters show what happens when capable people can't make the leap from operational competence to actual leadership. They know how the ship works. They just can't stomach what being the captain requires.

They're not bad people. They're not failures. They're just limited—by their own unwillingness to accept what they'd have to become.

Some people can make that transition. Some can't. Knowing which you are is valuable.

Here's the uncomfortable question Billy forces: is it better to be Billy or Flint? To maintain your integrity and fail, or compromise your integrity and succeed? To refuse the hard calls and remain innocent, or make them and become complicit?

The show offers no answer. Different people will choose differently. What matters is choosing consciously rather than pretending you're not choosing.

Billy pretends. He wants to benefit from Flint's choices while maintaining innocence. He wants the outcomes without the methods. He wants to eat at the table while condemning how the food was obtained.

That's the halfway crook position. Not committing to either path. Trying to have both. And the show is merciless in showing how that position collapses under pressure.

You're in or you're out. You make the hard calls or you don't get the outcomes those calls enable. You accept complicity or you leave the table. There's no neutral position. Neutrality is just complicity with better PR.

There's no such thing as halfway crooks. You're in or you're out. Billy keeps trying to be both.

It doesn't work.

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