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Whiskey Leaks — Operational Edition
Whiskey Leaks

Resist fascism and authoritarian rule.

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I Was a Trump Supporter. Here Is What It Took For Me To Wake Up.

This is a personal essay. Whiskey Leaks is publishing this on behalf of someone who reached out to us; someone who is struggling with what they see going on in their country everyday; someone who is coming to terms with past decisions and the consequences of those decisions.

I Was a Trump Supporter. Here Is What It Took For Me To Wake Up.
Photo by Jason Dent / Unsplash

This is a personal essay. Whiskey Leaks is publishing this on behalf of someone who reached out to us; someone who is struggling with what they see going on in their country everyday; someone who is coming to terms with past decisions and the consequences of those decisions.


I want to start with something that most people on the left will find hard to believe, and most people still inside the MAGA movement will immediately try to use against me:

I didn't fall for Donald Trump because I was stupid. I fell for him because he was good at what he does.

That distinction matters. Not for my ego (I've made my peace with having been wrong). It matters because if you write off everyone who supported Trump as simply ignorant or hateful, you will never understand how this happened, and you will never be able to reach the people who are still inside it. And some of those people are worth reaching. I know, because I was one of them.


2016: How It Started

By the time the 2016 election came around, I was primed.

I wasn't primed by hatred. I wasn't primed by racism, though I've had to do some honest reflection on what I was willing to overlook. I was primed by frustration: with a political establishment that felt distant and self-serving, with a media that felt condescending, with a sense that the country I knew was changing in ways nobody had asked me about or seemed to care how I felt about.

Trump spoke directly to that frustration. He was blunt where politicians were evasive. He was loud where the establishment was polished. He said things out loud that people around me had been saying quietly for years, and there was something intoxicating about that. The sense that finally, someone wasn't playing the game.

My family felt the same way. That mattered more than I'd like to admit. When the people you love and trust and have known your entire life are all moving in the same direction, the pull is enormous. Politics becomes tribal before it becomes rational, and my tribe was going one way.

So I went with them.

I want to be honest about what I was like in those early years, because I think it mirrors what a lot of his supporters are still like today. I was selectively blind. The things he said and did that should have been disqualifying, the mocking of a disabled reporter, the "grab them by the p***y" tape, the open contempt for anyone who questioned him, I explained all of it away. I told myself the media was exaggerating. I told myself he was just unpolished, not cruel. I told myself that what mattered was policy, not personality.

I was wrong on all three counts. But at the time, I believed it, and I believed it genuinely.


The Cracks

Disillusionment, when it's real, doesn't arrive all at once. It seeps in.

The first things I noticed were small. The way his cabinet turned over, and not because people were being replaced with better people. Anyone who showed any independence was eventually gone. The pattern became impossible to ignore: the people who stayed longest were the ones who agreed with everything, questioned nothing, and reflected his ego back at him. These were not the best people. They were the most compliant people. There is a difference, and it matters enormously when those people are running the departments of the federal government.

Then there was the money.

I'm not someone who begrudges wealth. I never have been. But there is something specifically corrosive about watching a man who campaigned on draining the swamp, on being so rich he couldn't be bought, use the presidency to enrich himself in ways that would have ended any other political career in any other era. The emoluments, the foreign governments staying at his hotels, the post-presidency grift machine of NFTs and gold sneakers and a cryptocurrency that made him hundreds of millions of dollars while his supporters bought in at the top.

He told us he was too rich to be corrupted. What he turned out to be was too shameless to bother hiding it.

By the end of his first term, I had started to say out loud, quietly, carefully, only to people I trusted, that something had gone wrong. That this wasn't what I signed up for. That the Republican party I had grown up believing in, the one built on personal responsibility and institutional respect and genuine conservatism, had been hollowed out and replaced with something that served one man's interests and called it patriotism.

I didn't have a word for it yet. I do now.


The Second Term: Where I Lost the Last of It

I had hoped, in whatever small irrational part of me still wanted to be wrong about him, that a second term might be different. That without the need to win re-election, there might be some governing. Some stability. Some actual delivery on the promises that had brought so many people to him in the first place.

Instead, what came was faster and harder and more openly contemptuous of the laws and norms that hold a democratic society together than anything in the first term.

The executive orders came in waves. The dismantling of institutions. The consolidation of power in ways that had no precedent in modern American governance. Each one was defended by his supporters as necessary, as bold, as finally someone doing what needed to be done. Each one chipped away at something that can't easily be rebuilt.

But the thing that broke whatever was left for me wasn't an abstract policy argument.

It was Alex Pretti. It was Renee Good.

These were not criminals. These were not people who posed any threat to anyone. Alex Pretti was a United States citizen, a citizen, killed during an ICE operation. Renee Good, the same. People whose lives ended not because of anything they did but because of what they looked like or where they were or the chaotic, reckless way these operations were being conducted.

And then the children. Families who were trying to do it the right way, following the legal process, presenting themselves at ports of entry, doing exactly what we always said immigrants should do, separated. Detained. Children taken from parents and put into facilities while their cases wound through a system deliberately designed to be as difficult and dehumanizing as possible.

I kept waiting for the outrage from the people around me. From my family. From the community I had shared politics with for years.

It didn't come.

That silence, that willingness to look at what was happening to real human beings and find a way to be okay with it, was the final thing I couldn't explain away. I had run out of explanations.


Talking to My Family

I've tried.

I want to be honest about this too, because I think a lot of people who have left the MAGA world have had the same experience, and it's one of the loneliest parts of it.

You cannot have a factual argument with someone who has decided that facts are a weapon being used against them. Every piece of evidence you present was either fabricated by the mainstream media, part of a deep state conspiracy, or evidence of your own brainwashing. The system is closed. There is no data point that can get in.

What I've come to understand, painfully, over years of trying, is that this is not a political disagreement in any traditional sense. Political disagreements can be resolved with evidence and good faith. What MAGA has become is a closed belief system with a leader at the center of it, and it functions exactly the way a cult functions: total in-group loyalty, dehumanization of the out-group, and an ironclad defense mechanism against any information that threatens the leader's image.

My family are not bad people. I want to say that clearly. They are people I love, people who have been good to me my entire life, people who I believe genuinely want what's best for this country. But they have been captured by something that has redirected that genuine patriotism and genuine frustration into something that serves one man and calls it America First.

I don't know how to reach them. I have stopped trying for my own sanity. But I haven't stopped hoping that something will eventually get through, not from me, but from the accumulation of reality pressing up against the things they've been told to believe.


What I Want To Say To Anyone Who Is Starting To Wonder

If you're reading this and something in it is landing, if there's a part of you that is tired of making excuses, tired of the cognitive dissonance, tired of watching people you believed in behave in ways you would never accept from anyone else, I want to say something to you directly:

You are not alone. And you are not stupid for having believed.

Trump is genuinely charismatic in a specific and dangerous way. He identifies real grievances and reflects them back at people with enough energy and contempt for the right enemies that it feels like finally being understood. That's not nothing. That pull is real. Being susceptible to it doesn't make you foolish. It makes you human.

But I want to ask you to do something that I think is harder than it sounds:

Think about who you were before he existed in your political life.

Think about what you actually believed, about fairness, about decency, about how a leader should behave, about what America is supposed to mean. Not what you were told to believe by a movement, but what you felt in your own gut, in your own life, before any of this.

Ask yourself honestly: does what you see now match that? Does the person at the center of this movement, the behavior, the vengeance, the self-enrichment, the contempt for due process, the willingness to let innocent people be killed or imprisoned as long as the optics serve the base, does any of that match the values you held before he taught you to hold different ones?

I think for a lot of people, if they're truly honest with themselves, the answer is no.

The Republican party I grew up believing in is gone. What replaced it is not conservatism. It is not patriotism. It is a personality cult organized around one man's hunger for power and money, and it has consumed people I love and a political tradition I once respected.

I'm not asking you to become a Democrat. I'm not asking you to agree with everything on the left, because I don't. I'm asking you to remember yourself. The self that existed before you were taught that half of your fellow Americans were your enemies. The self that knew, without being told, that children shouldn't be taken from their parents. That citizens shouldn't be killed without due process. That the president of the United States should be subject to the same laws as everyone else.

That self is still in there.

I know, because I found mine.


If this resonated with you, share it with someone who might need to read it. You don't have to agree with everything I've said. You just have to be willing to think. I'm now on the right side of the fight, and I know it. I will be working tirelessly to right the wrongs and help bring others into the light. You can find me on Twittter/X for now. That seems to be where the most people are who need help.

Chad Oakwood - https://x.com/GigaChad_4547