Why We Did It: A Travelogue from the Republican Road to Hell

America never would have gotten into this mess if it weren’t for me and my friends.

We were the “normal” Republicans. The pragmatic and practical. The “adults in the room” you hear so much about. Back in the early 2010s you might have found us networking with reporters at a bipartisan Bobby Van’s happy hour. Or making you wait one more second for our attention while we typed out an urgent missive on our BlackBerry device. Or appearing as the token right-winger on some onanistic Beltway panel.

Our Facebook profile picture may have been a backstage shot with Paul Ryan in his half-zip pullover. On Twitter we delivered devilish barbs mocking the Democrats for their disarray, tongue often planted in cheek.

We worked at corporate affairs firms or in “Boehner World.” We were Republican campaign apparatchiks and former Bush officials you see on the tube. We were opposition party operatives in exile, thriving in the meretricious capital, anxiously anticipating the moment when it was our turn to be the brash Josh Lymans conducting brisk walk-and-talks in the White House’s hallowed halls.

We may have been partisans, but the puckish sort. The “good ones,” unlike those crazy, mouth-breathing ideologues. Sure, we had conservative impulses. Fancied tax cuts and protecting babies and cutting red tape and what have you. We repped ’murica in a jejune back-to-back world war champs kinda way and could cite chapter and verse of Reagan’s Liberty State Park homily declaring that our nation’s golden door was the last best hope of man on earth.

You wouldn’t have confused us with populist revolutionaries. We wore pleated khakis, for Pete’s sake. (Well, I didn’t, but generally speaking.) At the time, populist revolutionaries weren’t even really a thing in D.C., besides the weird tricornered-hat cosplayers on the National Mall whose votes we cultivated but kept at several arms’ distance from our day-to-day lives.

When the Trump Troubles began there wasn’t a single one in our ranks who would have said they were in his corner. To a person we found him gauche, repellant, and beneath the dignity of the public service we bestowed with bumptious regard. We didn’t take him seriously. We didn’t watch The Apprentice. We didn’t get off on the tears of immigrant children. And you wouldn’t have caught us dead in one of those gaudy red baseball caps.

But, at first gradually and then suddenly, nearly all of us decided to go along. The same people who roasted Donald Trump as an incompetent menace in private served his rancid baloney in public when convenient. They continued to do so even after the mob he summoned stained the party and our ideals and the halls of the Capitol with their shit.

A few of us had tried to stand athwart the madness yelling stop before it was too late. Most tucked away their worries in a little box, easing their mind with a fanciful self-assurance that the Troubles would soon blow over. As they quietly acquiesced, others went whole hog, giddily swimming in his slop.

How did it all go to hell so fast? To what end did so many go along with something that had been anathema? And why didn’t the insurrectionist denouement make them say “enough” to this carnage of our creation?

These were my people. I should know.

* * *

A week after the Capitol riot I was in my pandemic bed/office when the messages started to roll in. My husband was the first, sending a link to our core friend group’s Lovelies text chain. The headline from the Associated Press: “Records: Trump Allies Behind Rally That Ignited Capitol Riot.”

“Lots of Wren content,” he wrote.

The physical response came before the reality of the news had really sunk in. My stomach turned, palms dampened, heart sank.

“Wren” was not just another in the endless parade of loathsome Trump cronies. She wasn’t one of those former colleagues whom I had come to consider with a mix of disgust and aghastment as the years went by. Wren wasn’t even “Wren,” to me.

She was Caroline. My friend. My campaign confidante. My concert buddy. Or, at least, she had been.

Then came another text and more cringing. According to the Wall Street Journal, Wren was named as a “VIP Advisor” on an attachment to the permit for the January 6, 2021, rally that preceded the deadly insurrection at the Capitol and she had worked on it with none other than InfoWars founder Alex Jones. The SMS that alerted me to this is still burned into my retinas. It read, “Caroline Wren texting people that Alex Jones is actually nice is too much for me.”

What in the actual fuck.

I reluctantly clicked. Despite being primed by that horrifying summary, the article itself managed to be more shocking than I anticipated.

“In text messages Ms. Wren sent to another organizer and reviewed by the Journal, Ms. Wren defended Mr. Jones. ‘I promise he’s actually WAY nicer than he comes off. . . . I’m hoping you’ll [sic] can become besties,’ Ms. Wren wrote.”

The best you can say about those few dozen gobsmacking words is that it might be technically true that Alex Jones is “way nicer than he comes off,” given that he comes off as the acrid embodiment of everything that is wrong in our society. As for the possibility of becoming “besties” with him, well, even taking into account the most generous possible reading of that text, even recognizing that I had myself played footsie for professional purposes with similarly awful people, it is still hard to wrap one’s mind around how a person could type that without becoming overwhelmed with revulsion at oneself. This is Alex Jones, after all. The human ass-pimple best known for defaming and harassing the mourning parents whose innocent little children had just been executed by a monster at Sandy Hook Elementary School. Just think of how warped and wicked you have to be to target, without any remorse, people coping with the most intense grief that can be imposed on a human being. Now my friend is in the newspaper, saying he isn’t all that bad. That if people got to know him, they might be “besties.”

How am I supposed to comprehend that?

Later that day a reporter texted posing that very query. “How {did} she fall prey to this deal? Just thirst?”

I paused to consider it. Nine years earlier we had worked together on the campaign of the most moderate Republican presidential candidate of the twenty-first century. In the ensuing decade, we had become genuine friends. Not the type of D.C. “friend” that is really just a work acquaintance whom you make small talk with at happy hours. An actual friend. We went to see Portugal. The Man together, about a half decade before they were on the radio. She’d hassle me over text until I got out of bed to meet her for a drink because she was only in town for the night. We browned out at a club in Miami and in some dive bar in Columbia and at the 9:30 Club and in her basement and well . . . lots of places. I was invited to her yearly “Wrenpalooza” birthday party. Our closeness persisted even when we weren’t partying. She was the kind of friend with whom I would share private worries and fears that only a small group of people were privy to. I leaned on her when my husband and I were going through adoption troubles after our first attempt went south. And she on me when a relationship hit the skids.

How did we end up so far apart?

Here’s how I responded to the reporter: “Thirst. Likes being in the mix. Thought it was a fun game and people were overreacting. Oops.”

That was my theory, at least. But I didn’t actually know if it was the truth.

By the time I had sent that text, Caroline and I were no longer “friends” in the active sense. In March 2016, I texted her, cheekily, “Stop with the Trump stuff. I will unfriend u.” But what I thought was an empty threat at the time became our reality.

By 2021 we were still “friendsish,” to use a technical term. But we weren’t sharing secrets. I didn’t know what was going on in her personal life. We weren’t even able to talk about one of the most consequential matters facing both of us—our work, the president, the state of the country.

It had been almost two years since I had seen her, and the last time we had gotten together, I had purposefully avoided the tiny-handed elephant in the room. She had come to Oakland and hung out with my husband and daughter, whom she adores (obvs). Along with a mutual friend, the five of us went to dinner at a foodie restaurant by Lake Merritt. We talked about the latest childhood milestones and gossiped about old mutuals. For most of the dinner, there was no real discussion of “the news,” unless you count sharing a little goss about who various political figures were hooking up with.

Toward the end of the night, our pleasant détente was broken when my husband couldn’t resist and made a swipe. Both of their necks turned a shade of eggplant, and they parried. I don’t remember the specifics of the quarrel. I tuned it out, focused on breathing deep breaths, and pretended to attend to some unnecessary toddler parenting until the exchange came mercifully to an end. It wasn’t exactly the most courageous move. But I had had enough relationships go sour over Trump by that point and had decided that when it came to resentment of past pals, my heart was full up. That night I never even asked her about her foray into Trump world. Didn’t learn that she was about to take a senior role as the finance director on his reelection campaign.

I just compartmentalized this part of our life. As the weeks went forward and she became increasingly intermingled with the Trump high command, I unfollowed her on Snapchat and muted her Instagram stories to protect my blood pressure from the spikes of seeing her in social settings with random MAGA maroons. A year later, she was across the bridge in San Francisco and invited me to join her for drinks with Donald Trump Jr. and his girlfriend, former Fox News talker Kim Guilfoyle. She was planning to take them to the Tonga Room, a classic tiki bar in the finance district, because, according to her, Kim would “love the scene.”

For a moment, I considered it, if only for the story. I mean, how often do you get invited to an intimate happy hour with one of the most loathsome people on the planet and also Donald Trump Jr.? But I couldn’t imagine how we could have survived even a single drink without risking a physical altercation, given how plain my disdain for them would be. I have the world’s worst poker face and a tendency toward blurting out my internal monologue. It was possible I would have told Don to go fuck himself the moment he came inside my field of vision. I did the prudent thing and declined.

After that, we basically just ghosted each other.

All this is to say, I didn’t truly know exactly how she “fell prey to this whole deal,” how a former pal had become a coup conspirator . . . because we didn’t talk about it. Was it really all just a big game, like I had assumed? Did the person who I thought was a like-minded Republican in Name Only (RINO) squish genuinely want to overthrow our democracy to install Donald Trump as an unelected quasi-autocrat?

To find out, I would have to reanimate the relationship we had once had.

So, five months after the insurrection pregame party that she had organized on the Mall, Caroline and I found ourselves sitting by the bay windows in the Hotel Casa del Mar’s Terrazza Lounge, looking out at the Ferris wheel on the Santa Monica Pier, sun beating down through the glass. I was nervous, the palms of my feet and hands dampening.

How exactly do you start a conversation that requires a complete rewiring of your friendship? That might end it for good? Part of me wanted to just lean right in. To shout, How are you still going along with this shit? But a fight about Donald Trump wouldn’t illuminate anything; we’ve all had plenty of those.

In order to truly understand what happened, I needed to not just listen to her rationalizations and explanations about January 6th. I needed to figure out where our parting had started. Whether the common ground I thought we had shared ever really existed at all. I needed to look at myself through her and try to understand what it was I had done that made all those whom I had worked and partied alongside feel so comfortable going along with something so horrible.

* * *

Why We Did It is a book about the people who submitted to every whim of a comically unfit and detestable man who crapped all over them and took over the party they had given their life to. It’s about the army of consultants, politicians, and media figures who stood back and stood by as everything they ever fought for was degraded and devalued. The people who privately admitted they recognized all the risks but still climbed aboard for a ride on the SS Trump Hellship that they knew would assuredly sink.

I suspect that prospect will excite many of my fellow Trump detesters who come to this book craving a dollop of delicious schadenfreude and the satisfying comfort food that can only be baked by an apostate Republican validating all their liberal readers’ prior biases. And, well, I cannot tell a lie: there will be some of that warm apple pie to come.

But my objective is not to execute one continuous Dr. Dunkenstein jam that lays waste to the craven former colleagues who submitted to their new idiocratic overlord. Nor to disembowel Trump’s most deranged and debased allies: the racists and the conspiracists and the sociopaths who clung to his stink. There has been plenty of that already. And, if you are feeling a dearth of dunking in your life, well, my Twitter feed is a smartphone away.

Why We Did It aims to get at something deeper than that. To dig through the wreckage of the party I once loved and come to understand how so many of my friends allowed something that was so central to our identity to become so unambiguously monstrous. And why they had continued to do so once the monster became uncontrollable.

Grappling with that requires first understanding how our actions helped lead us to that dystopian escalator ride. How we got people familiar enough with unseriousness and cruelty that they would giddily glide down with him. I’m sure a student of history might be able to trace it back to the Southern Strategy or Lee Atwater or, hell, maybe even Mark Hanna (give him a Google).

But my soul required coming to terms with something that was more intimate than that. A question that I had grappled with throughout the entire Trump era.

Why in the fuck did the vast, vast, vast majority of seemingly normal, decent people whom I worked with go along with the most abnormal, indecent of men? And why hadn’t I seen it coming? If we are to summon even a hint of value from our manifest failures throughout this whole sordid mess, to find any guideposts for bringing people into the light—those were the questions that needed answering. Answering them required plumbing the complicated motivations of real, living humans.

So, I decided to retrace their steps and mine.

The first half of this book examines the journey I took walking right up to the ledge. From the McCain/Palin prelude to playing footsie with Steve Bannon and the worst of the alt-right. It covers the red flags I saw and ignored. The ones I missed. The secrets I kept. The brutal slams I imposed on my imagined enemies. The friends I made along the way. That solipsistic reflection will, I hope, shed some light on how damn easy we made it for others to take the plunge right on over the cliff I managed to veer away from.

Some of the stories will be familiar—after all, they were news. However, you’ll now have a chance to view them in a more reflective light from a person who was orchestrating them. Things like Mitt Romney’s IBS-riddled dog being strapped to the car roof or the origins of Crooked Hillary.

There will be other stories and anecdotes that might have otherwise been lost to history, but which I revive because they are emblematic of the various complexes that led us to this distressing moment. The first is how many of the players in the upper echelons of American political life treated their duties as a big game, where they awarded themselves the status of public service while minimizing the responsibilities of that service in favor of performance and skulduggery. How success in this era was so often completely removed from political beliefs. Should it have come as a surprise that a game show host was so successful at co-opting a system as puerile as that?

You’ll also see how the Republican ruling class dismissed the plight of those we were manipulating, growing increasingly comfortable using tactics that inflamed them, turning them against their fellow man. How often we advanced arguments that none of us believed. How we made people feel aggrieved about issues we had no intent or ability to solve. How we spurred racial resentments and bigotry among voters while prickling at anyone who might accuse us of racism. And how these tactics became not just unchecked but supercharged by a right-wing media ecosystem that we were in bed with and that had its own nefarious incentives, sucking in clicks and views through rage hustling without any intention of delivering something that might bring value to ordinary people’s lives. Should it have come as a surprise that a charlatan who had spent decades duping the masses into joining his pyramid schemes and buying his shitty products would excel in such an environment? Someone who had a media platform of his own and a reptilian instinct for manipulation? Someone who didn’t hesitate to say the quiet part aloud?

This brings us to our second, more complex psychological journey. After our past sins were anthropomorphized into an Archie Bunkeresque president, what to make of those who saw his defects clearly and went along anyway?

What was it about them or the system that rewarded such behavior? Going full MAGA was never clearly prestigious or in service to their ideological priors. There was no certainty that the ends would justify the means. Many who threw in with Trump were ruined by him. Why strive for proximity to power when the costs are so great and you don’t even know what you want to get out of that power when it falls in your lap? That’s the puzzle.

Throughout this reflection, I attempt to put forth a more fully formed, you might say actualized, understanding of my own rationalizations—as a gay man who worked for homophobes, an oppo research magnate who giddily stirred up artificial animus, a clear-eyed Trump loather who still took a bite of the poisoned apple (we’ll get to that).

It’s through this process that I hope to inhabit the mindset of those who came to terms with Trump. Because—and this is important—many of the people who did so are not all that different from me. In our conversations they defended their choice using many of the same justifications I had in the past. These people are not all barbarians or megalomaniacs. They are flawed men and women with shadow wants and desires. It’s just that in this case those desires allowed them to accept an unusual evil.

Some of their rationalizations were unique to the Republican Party; others were the more universal failings replicated throughout industries and societies and political ideologies across the sands of time. Some of them were in the ballpark of defensible; others will fill them rightly with shame. Some are still grappling with these choices, while others have given up and embraced their complicity.

The manner in which people made these allowances for themselves will be told through the vantage point of my colleagues on the Republican autopsy, a project that had proposed a more welcoming and uplifting trajectory for the GOP and featured a representative sample of the key men and women in the fallen former Republican establishment. The actions of these characters—and of an additional representative few who either volunteered to come to church or required an involuntary dunk in the font—will, I hope, paint a complete picture of why those in proximity to power did what they did and why it’s going to be so hard to get any of them to reverse course.

One of Trump’s most shameless enablers is a congressman from Texas named Dan Crenshaw. Crenshaw is seen by some as a rising star in the party. He is like many of the characters you will meet over the course of this book. Someone who knew better and told us he knew better but went along with the hateful, bigoted, blundering Trump anyway. He wrote this in his book on “leadership”: “After every failure, after every hardship, we create a personal narrative to account for that moment. We tell ourselves a story.”

On this count, Crenshaw is exactly right. He and his fellow accomplices committed one of the biggest failures of the modern era. They decided to abet a man that they all understood to be a danger. A man who remains a fundamental threat to the very fabric of our democracy even after his defeat.

What I will submit to you are the stories, the narratives, that those who are a party to this failure tell themselves to account for their actions. In all their hypocritical, oblivious, self-indulgent, resentful, and at times well-meaning glory.

I will warn you. This journey is a depressing one in toto. But our peripatetic path to the abyss won’t be bereft of levity, as it is written in the spirit of my most sacred maxim.

In trying to understand what’s happening in politics, when in doubt, remember it is always, always Veep . . . not House of Cards. As a result, there will be no shortage of Jonads and sphincters, and jolly green jizzfaces to lighten the load.

Enjoy . . . if you can.

Contents

Cover

Title Page

Dedication

Epigraph

Introduction

1. The Comforting Lie

2. Compartmentalizer-in-Chief

3. The Game

4. Gay Traitor Degrading the Discourse

5. Centering the Comment Section

6. Red Meat for the Crocodiles

7. The Breakup

8. Inertia

9. The Enablers

10. The Little Mix

11. The Nerd-Revenging Team Player

12. The Strivers

13. The Cartel-Cashing, Team-Playing, Tribalist Trolls

14. The Junior Messiah and the OG Demagogue

15. The Demonizer and the Never Trumper

16. The Big Lie

Acknowledgments

Index

About the Author

Copyright

About the Publisher