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Lesson 2

More Cowboys… Less Bureaucrats

"When governments grow bloated and bureaucracies become oppressive, only the bold can keep freedom alive."

Gregory Keough

I've lived this lesson from the inside. When I joined the CIA, my mission was to be a Cowboy, a warrior for freedom. But to get the job done, we had to fight a war on two fronts. One against the enemy overseas. And another against the Bureaucrat mindset in our own headquarters.

I've seen bureaucrats in silk ties do more damage than the enemies we fought overseas. I've seen the "system" reward those who avoid risk and punish those who take it.

We are in a global war of values: Cowboys versus Bureaucrats.

There can be no middle ground.

My mission is to raise my kids as Cowboys.

When I say Cowboy, I don't just mean literal cowboys. Though they're included.

I mean people who embrace a Cowboy-like view and attitude toward life.

Cowboys love freedom, take risks, stand by a handshake, fight to the last breath to save their family and home, and have no neutral ground on core issues.

When the law and bureaucrats are wrong, they stand up.

This is why Americans love Cowboys. The soul of our nation is in the Cowboy.

Cowboys possess: Vision, Conviction, Courage, Determination, Optimism, Endurance, Responsibility.

The Cowboy spirit once defined America. Storming Normandy. Going to the moon. Building the modern world.

But here's the difference. Back then, they had something we don't: a Cowboy army behind them.

Millions of men and women who believed in hard work, truth, sacrifice, faith, family, and freedom. Without needing to be convinced or coddled.

Those values were common. Today, they're controversial. That's the real crisis.

Let me be clear: when I say Cowboy, I don't mean male.

I mean courageous, mission-focused, truth-upholding. And that includes women.

I tell my two daughters this often: You're Cowboys. And I mean it.

Bravery and grit know no gender.

Bureaucrats hate Cowboys. They are failed Cowboys. Either lacking the guts or having given up.

They use rules and laws to control Cowboys because they can't win in a fair fight.

Bureaucrats have weaponized the law. Criminalizing everyday life and using it to go after anyone who steps out of line.

I have experienced this firsthand. The federal government boasts a 99% conviction rate, often targeting crypto and white-collar cases while ignoring cartel kingpins, violent offenders, and the corruption of the powerful.

Facts don't matter. Truth doesn't matter. Innocence doesn't matter. Once you're in, the only way out is through.

You have a choice: be a Cowboy or a Bureaucrat.

Cowboys live with purpose. They know who they are and what they stand for.

They trust themselves, not the system.

Cowboys create their own security. By betting on themselves.

Bureaucrats want you dependent. Cowboys want you free.

People like to talk about fighting back.

Most of them have never done it.

Real resistance does not trend. It does not get you invited to panels. It usually costs you friends, income, reputation, and sometimes your freedom.

The people who actually resist are not celebrated. They are punished. They are fired quietly. Debanked. Labeled problems. Pushed out of institutions they helped build.

Some spoke up publicly and paid for it. Most resisted privately, by refusing to comply, refusing to lie, refusing to surrender their conscience even when it would have been easier.

You will not see statues for them. History rarely rewards courage in real time.

Resistance is lonely.

And here is the uncomfortable truth: most people do not fail because they are evil. They fail because they are afraid. Afraid of being isolated. Afraid of being labeled. Afraid of losing what they have spent their lives building.

The system understands this perfectly.

That is why modern control does not require soldiers. It only requires incentives and fear.

And that is why the people who do resist, truly resist, matter. Not because they were loud.

But because they were willing to lose.

The most dangerous Bureaucrat isn't in Washington: it's the part of you that trades courage for comfort.

The Cowboy way demands sacrifice, grit, and a deep belief in something bigger than yourself.

Saddle up. Or get left behind.

• • •

The song this chapter runs on▶  Rich Men North of Richmond, Oliver Anthony · Spotify

“Lord knows they all just want to have total control”

THE GRINDER

• • •

When I was in my first hearing, I still believed the process worked as advertised. Innocent until proven guilty. A search for facts. Fairness.

I was wrong.

The government's argument for detaining me without bail was simple: they said I had fled the country.

That was a lie.

We were living in El Salvador. I had a residency permit. We'd built a life there.

My attorney sent a letter to the U.S. Attorney in charge of the case stating I would voluntarily return. It's in the record. He called the FBI office directly: "If you want to come in, come in. We're here."

They never responded.

What they accused me of had already been reviewed by a federal trustee, with an FBI agent present.

The trustee testified under oath: no evidence I had anything to do with it. None.

Loans I didn't fill out. For a company I no longer ran. For money I didn't receive. Loans that were paid back in full.

My bail was set at \$3 million. My attorney said it was one of the highest he'd seen in that courthouse.

The guy who actually submitted the loans? Same case. \$150,000.

I kept asking myself if I was missing something. Some mistake I'd made that I wasn't seeing.

That's when I understood what I was in.

The grinder.

A machine that does one thing. Softens you up. Spits you out.

Once you're in, the only way out is through the other side.

Even the U.S. Marshals knew I shouldn't be there.

They'd ask, "Mr. Keough, is today the day?"

I'd reply, "Only the Good Lord knows."

My lawyer told me they were pissed. No 20-man SWAT raid. No scene. Because we were living in El Salvador, I wasn't there to give them their moment.

So they used my background against me. Called me a flight risk.

If I didn't want to be found, they wouldn't have found me.

But I came back. Willingly.

There are four stages before general population.

First, the holding cell. Concrete and fluorescent light. No clock.

Then upstairs. A few days. Waiting.

Then quarantine. Fourteen days. Twenty-four-hour lockdown. No daylight. No exit except to shower.

Then general population.

It was upstairs I met the crapper.

He was having issues with his cellmate. A quiet man who kept to himself.

The crapper lost it. His solution: defecate on the man's bed.

The victim walked out into the hall and yelled:

"Who the hell took a shit on my bed?!"

The cell erupted.

Quarantine.

As they lined us up for the elevator, guess who was standing right in front of me.

The crapper.

Fourteen days. Locked in. With him.

I whispered, "Lord, if this is a test, it's a tough one."

The elevator stopped. First floor.

They pulled him out.

I stayed with my guys.

The Colombian taught us how prison really works. Knew every angle, every trick, every trap.

But every night, same thing. They'd bring the phone to the cell. He'd call his kids.

I'd watch him talking. Voice soft. Trying to sound normal. Telling them daddy was okay.

Then he'd hang up and go quiet.

That's when it hit me. What awaited me. What this would do to my family. My kids.

The grinder doesn't just grind you. It grinds everyone who loves you.

After quarantine, they move you into general population.

Noise. Movement. Eyes.

At intake, they take your name and replace it with a number.

They say do your time and you're done.

You're never done.

They put everything on the internet. Your name. Your mugshot. Their version of the story. Forever.

This was the first of three facilities.

At sentencing, the government tried to throw me back in jail. In front of my family and my priest. Said I was a flight risk. Despite full compliance.

The judge didn't allow it.

I self-reported to Alabama. They knew who I was.

When I arrived, they moved me to a state prison and put me in solitary. The place they send people who are problems inside the system. Not people who just walked in the door.

Even the guards couldn't believe it.

That story is for another time.

They thought they were grinding me down.

They were sharpening me.

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