I sat in silence watching the second hand of a silver clock on the wall spin slowly during a commercial break. It had been a long time since I’d been nervous going into an interview. For some reason, though, this one was different. This one felt different.
On August 21, 2015, I was the CEO of a fast-growing Alabama media company called Yellowhammer, which began as my blog when I was a student at the University of Alabama a few years earlier. I focused on state politics and the behind-the-scenes machinations of lawmakers. My biggest weekly feature was “Rumors and Rumblings,” giving the scoop on what was really going on inside the Alabama State House. The site initially attracted a hard-core following among state politicos from both parties, but within four years our readership had exploded. Now I was in the Yellowhammer Radio studio in Birmingham, preparing to interview the most unlikely of presidential candidates, Donald J. Trump.
That evening, he was slated to visit the state for the first time for what was predicted to be the largest event in the history of presidential primaries. Tens of thousands of Alabamians were expected to pile into Ladd-Peebles Stadium in Mobile to witness what The Washington Post later described as “something between a Lynyrd Skynyrd concert and the Daytona 500.” They weren’t far off.
I had made several attempts to get the Republican candidate to appear on my radio show in the run-up to the event, but all my calls and emails went unanswered. When a rival radio host did land an interview, I fired off a terse email to the campaign to explain that it made no sense for Trump to do that other show instead of mine because our reach was so much greater, and we also had a large online platform. I figured some staffer would read that email and think, Okay, big shot, you’re definitely not getting an interview now. But, to my surprise, I was contacted by a press aide named Hope Hicks.
“Eleven-thirty your time, okay?” she asked. Perfect. It was on.
Later, when we met in person for the first time, she laughed when she found out that we were about the same age. “Your emails made me think you were a cranky old man!” she said.
It was still unclear, at least to me, whether the Trump candidacy was a fad—a chance for voters to vent their frustration with political correctness and the status quo before they got serious with another candidate. Predictions of Trump’s imminent implosion, over one incendiary thing he said or did after another, were an almost daily occurrence. A pollster I knew who had worked for Trump in the past told me privately that the billionaire tycoon didn’t actually want to win the presidency, but rather viewed the race as a once-in-a-lifetime promotional opportunity for his brand.
And yet there was something—something that made it hard to pass this all off as a lark. Other presidential contenders had called in to my show before, but none elicited the office-wide response that Trump did. Nearly everyone in the building, it seemed, was gathering around to bear witness to a live interview with “The Donald,” an aggressive billionaire real-estate developer turned boisterous reality TV star turned presidential front-runner. He’d be a thousand miles away.
A poll released the week before showed Trump lapping the rest of his Republican opponents in Alabama. But it wasn’t his polling numbers that made me nervous. It was his entire larger-than-life persona. I’d watched him steamroll interviewers in the past, some of the best in the business, with long, occasionally rambling, monologues until time was up. I didn’t want to be the next victim. I was planning to ask him some tough questions—the kind my mostly conservative listeners were asking themselves.
I was snapped out of my contemplative state by music blaring from the headphones sitting on the table in front of me, signaling the commercial break was over. I looked up at the computer screen, which displayed the phone lines. “TRUMP,” my producer had typed on the line identifying the caller. Here we go.
“He’s defying political gravity in a way that we’ve never really seen before,” I said. “He is Donald Trump, and he joins us now. Mr. Trump, how’re you doing today?”
“Very good, thank you very much, Cliff,” he said. “I appreciate it.”
There was no denying his popularity in Alabama, nor the fact that his message—particularly on the issue of illegal immigration—was resonating with a wide swath of the electorate.
With that in mind, I started by asking him if, should he win the presidency, he would consider nominating Alabama’s popular United States Senator Jeff Sessions—a fellow immigration hard-liner—to serve as his Attorney General. Looking back, I guess you could say that was the first piece of advice I ever gave him.
“He’s a great guy, and while it’s a little early in the process, I’d like to get there first, and I have to get there,” Trump answered. “Alabama is lucky to have him, and he’s lucky to have Alabama, but frankly, when I was getting very, very serious on this immigration thing, because as you know it’s out of control, I took tremendous abuse.… What’s happening at the border is a disgrace.”
We went on to discuss a variety of issues on which conservatives were hoping to get some assurances, from abortion to gun rights to religious liberty.
“Conservatives around the country really love what you’re saying,” I told him. “But when I hear criticisms of you from conservatives, and even some of the reservations I have myself, it really comes down to some of the past positions that you’ve held on issues that we really care about.”
“I understand that,” Trump replied.
He had come under scrutiny for his many contributions to Democratic candidates over the years—including the Clintons, who were probably two of the most disliked politicians in all of Alabama. He’d also made a number of comments over the years that seemed to put him somewhere between Chuck Schumer and Nancy Pelosi politically.
“So, for conservatives who are trying to give you the benefit of the doubt,” I continued, “can you walk us through your personal journey that led to such profound shifts in your philosophy and ideology?”
“Well, it’s timing. And you have to understand I was a businessman,” he calmly explained. “So I’m pro-life, as an example. But when somebody would say, ‘Are you pro-life or pro-choice?’ or whatever they might ask, it was, like, something that I never really would express.… I’m not sure I was ever asked the question until I was in the world of politics.”
That wasn’t entirely true. I’d done my research on this point. “Well, somebody asked and you said that you were very pro-abortion at one point,” I interjected.
“No,” he shot back. “What I said is that I hate the concept of abortion. I think it was the first time it was ever asked of me. Because I hated the concept of abortion.”
The quote we were both referencing came from an interview Trump gave to the late Tim Russert on NBC’s Meet the Press a year before the 2000 election, one of several previous election cycles when he toyed with the idea of running for President. Trump did, indeed, say during that interview that he “hated the concept of abortion.” But he had also said he was “very pro-choice”—a fact he now wanted to gloss over as if it never existed. This would, of course, be a recurring habit.
But then he added more to his answer that seemed to suggest he’d given abortion more thought than he’d been given credit for. “Ultimately I changed because I had two friends that were going to have a baby and they were going to terminate that baby—they were going to have an abortion—and they didn’t do it,” he explained. “And their child has turned out to be so incredible. So every time I see them they say, ‘Can you believe that we were thinking of…’ I know the child, the child is a phenomenal person.… I’ve seen things like this over the years, so I evolved on that.… But I’m pro-life.” As I got to know Trump, he’d often cite various nameless “friends” whose statements or experiences fit neatly into whatever point he wanted to make. Sometimes reporters wondered if those friends existed. But in this case, I had no reason to think he was being insincere.
I also wanted to get Trump talking more about his faith, which was important to me personally. Like many kids who grew up in the South, I was in church every Sunday morning and Wednesday evening. For me, it was more like every day of the week, though, because my dad was a pastor and my mom was the church pianist. Like many preachers’ kids, I’d rebelled in my teenage years, but later returned to my roots.
My granddaddy James Breland was a pastor, too. He was approaching ninety years old and still preached at a country church in the Mississippi Delta every Sunday. Before his wife, my Mimi, passed away in 2015, she had been the volunteer church librarian. She was also an avid note writer. Every photo on the walls of their home was meticulously documented. She wrote down funny things that happened or quotes she wanted to remember, all in the perfect cursive handwriting that could only belong to a schoolteacher. We don’t know exactly when she did it, but before she passed away, she left one final note tucked inside her checkbook—but this one wasn’t for her, it was for my granddaddy. She knew where to leave it so he would find it, and he did, just a few days after she died.
“Please don’t cry because I died!” the note said. “Smile because I lived! Know that I’m in a happy place! Know that we will meet again! I’ll see you there!” I wrote an article about the note on Yellowhammer and it went viral all over the world, with stories in People magazine, on the Today show, and dozens more.
Needless to say, I was raised to believe that faith is the foundation of character. At the time, my faith was one of the reasons I struggled with Trump’s unexpected rise. The playboy past, the casinos, the profanity, a seeming lack of common decency—all of it was tough to swallow for a Southern boy with Baptist ministers for a father and grandfather.
Ideologically I was more aligned with Ted Cruz, a rock-ribbed conservative who’d been giving the party establishment fits since getting elected to the Senate a few years before. Stylistically I was drawn to the aspirational tone of Marco Rubio. Time magazine had dubbed him “The Republican Savior” in 2013, a time when conventional wisdom held that Republicans would struggle to ever win a national election again unless they became a “Big Tent Party.” For the GOP establishment, this meant softening the party’s stance on immigration. On that point, I couldn’t have disagreed more. I know people have different views on this, but without a border, you don’t have a country. Without the rule of law, you don’t have a republic. Without assimilation, you don’t have a culture.
Most candidates seemed oblivious to the power of those issues, which were affecting millions of people, economically and socially. Trump owned those issues, and the intensity around them fueled his meteoric rise. I’d met Alabama coal miners who’d lost their livelihoods and the local steelworkers who blamed the dumping of Chinese steel for their jobs getting cut. I’ll never fully understand how a billionaire from Queens intuitively understood Middle America better than Republican politicians who’d spent their entire lives in the heartland—but he did.
Yet I was still concerned about these character questions. Earlier that summer, during an event organized by several faith-based organizations, Trump had identified himself as a Protestant. But when asked whether he had ever felt inclined to ask God to forgive him for any of his mistakes, his answer raised some eyebrows, including mine.
“I don’t think so,” he said. “I think if I do something wrong … I just try and make it right. I don’t bring God into that picture.”
When I raised the topic, he went straight to one of his favorite tactics: citing polls in lieu of answering the question directly. “There was a recent poll where the evangelicals said that I was their number-one choice.”
That gave me an opening to dive in. “There are a lot of evangelicals here in Alabama,” I told him. “This is something that really matters to us. Faith is an important part of our lives.”
“Yes,” he said. “For me, too.”
“Tell us a little bit about your stance on religious liberty,” I continued. I told him many of my listeners were alarmed by details of recent Supreme Court decisions that found a church, a mosque, a synagogue, or another faith-based nonprofit could lose their tax-exempt status or be compelled to act against their sincerely held religious beliefs, such as not providing health care for abortion-inducing drugs or only conducting marriage ceremonies between a man and a woman.
“Talk to us,” I went on, “about what a Trump administration would look like with regard to religious liberty.”
He basically ignored all of that and went somewhere totally out of left—well, right—field. “There’s an assault on anything having to do with Christianity,” he replied without hesitation. “They don’t want to use the word ‘Christmas’ anymore at department stores.”
I leaned back in my chair and smirked. Where’s he going with this?
“There’s always lawsuits, and unfortunately a lot of those lawsuits are won by the other side. I will assault that. I will go so strongly against so many of these things. When they take away the word ‘Christmas,’ I go out of my way to use the word ‘Christmas.’”
Whether someone agreed with this position or not—and my listeners loved it—it was easy to see the genius behind it. He’d taken a complicated subject and instead of discussing what he undoubtedly thought were boring things—like Supreme Court cases and the federal judiciary—he turned the issue into something people could instantly relate to.
Why don’t “they” let us say “Merry Christmas” anymore? Trump’s constant railing against “them” helped create a deep connection between himself and his fans. They were in this fight together—against the elites, the Republican establishment, the Democrats, or whoever else they believed was holding them down.
The clip went viral, sweeping across the internet in spite of the fact that we were talking about Christmas in the middle of the summer. And also despite the fact that just six months earlier President and Mrs. Obama had sent out a message from the White House wishing Americans a “Merry Christmas.” This was my first direct exposure to Trump’s ability to distill an argument down into a bite-sized nugget packed with symbolism, even if it wasn’t entirely aligned with the facts. It was a speaking style built for the age of social media and 24/7 cable news. In a world of “Happy Holidays,” he was a “Merry Christmas” missile, locked and loaded on the politically correct elites.
This was far from the only example of Trump’s marketing genius. I also believed that “Make America Great Again” was perhaps the single most brilliant piece of political branding in modern American history. Though many on the left characterized the term as having racial undertones, not everyone saw the phrase that way. After all, even then-President Bill Clinton said in a 1991 speech, “I believe that together we can make America great again.” The idea tapped into a deep-seated belief and anxiety among many Americans—people I knew growing up in the Deep South—that the country they had grown up in was slipping away from them. It reminded me of a scene from AMC’s hit TV show Mad Men, which dramatized the inner workings of a Madison Avenue ad agency in the 1960s. In one of the show’s most poignant scenes, Don Draper, played by actor Jon Hamm, introduces his plan to market a home slide projector made by Kodak.
With the lights in the room dimmed, Draper flips through photos showing pivotal moments in the life of his family—his wedding day, his pregnant wife, his young children playing together. “There’s the rare occasion when the public can be engaged on a level beyond flash,” he began. “If they have a sentimental bond with the product … nostalgia. It’s delicate, but potent.… In Greek, ‘nostalgia’ literally means the pain from an old wound. It’s a twinge in your heart, far more powerful than memory alone.”
As the room sits in rapt silence, Draper explains that the slide projector is “a time machine. It goes backwards, forwards. It takes us to a place where we ache to go again.… It lets us travel the way a child travels—round and round, back home again, to a place where we know we were loved.”
While Donald Trump would never speak in such sentimental terms, his political slogan was channeling a profound sense of nostalgia that lived inside millions of Americans. And much like Barack Obama’s “Hope” and “Change” slogans, the power of MAGA was that each person could define the ambiguous phrase in whatever way suited them personally.
After our thirteen-minute interview ended, I pushed the Trump campaign to the back of my mind. The 2016 presidential race was a peripheral concern for me, especially as I was embroiled in a political circus much closer to home.
In March of 2016, a source contacted me with a tip. They had a thumb drive for me, which I could only retrieve if I was willing to meet behind an obscure Birmingham gas station at midnight.
As I drove up U.S. Highway 280, swerving in and out of traffic and making my way from suburban Birmingham toward the city’s center, I thought about the events of the past year that had led up to this moment.
For many months the hottest rumor in Alabama politics was that long-married Republican Governor Robert Bentley, seventy-seven, had engaged in a long-running extramarital affair with his senior political adviser, Rebekah Caldwell Mason, forty-four, herself a married mother of three. At first the idea seemed so absurd, I dismissed it as politically motivated nonsense.
For the week prior to this midnight meeting, I had been in discussions with confidential sources who claimed to be in possession of secret audio recordings of Governor Bentley and Mrs. Mason. The recordings, I was told, contained explicit details of the Bentley-Mason affair. The sources were wary of their identities being revealed, and one of the sources expressed concerns about the Bentleys’ grandchildren having to endure such embarrassment.
But they agreed on three key points:
Number one, that Bentley—the husband, father, church deacon, dermatologist, and now Governor—had allowed his once-sterling character to be corroded by power.
Number two, that Mason—the former local TV news anchor, small-time communications consultant, and now senior adviser to the Governor—had willfully destroyed the Bentleys’ marriage of fifty years (they ultimately divorced) while simultaneously consolidating near-full control of the executive branch of Alabama’s state government.
And number three, that the evidence they held could spark a seismic event in Alabama politics and bring the Bentley-Mason house of cards crumbling down.
In spite of their reservations about releasing the recordings, it was Governor Bentley’s arrogance, one of the sources said, that was too much for them to endure. While Mrs. Bentley struggled to understand what all had happened and mourned what she felt like was catastrophic damage to her “Christian witness,” her husband continued to give his mistress unfettered access to every part of his life.
As he walked down the center aisle of the Old House Chamber after delivering the State of the State address, Mrs. Mason was by his side. When he was photographed at a swanky Washington, D.C., gala typically reserved for only governors and first ladies, she was his date. And when any meeting in the capitol was concluded, she was always the last one left in the room with him. The frustration and anger simmered for months, but it was now boiling over.
I pulled behind the gas station to find my source waiting exactly where they said they would be. The episode felt like a dramatic scene out of a spy movie, complete with me hopping out of my black sedan, 9mm pistol tucked in my waistband. Not a single word was spoken. My source handed me the thumb drive, and we both turned around, stepped back into our vehicles, and sped away. When I made it home fifteen minutes later, I plugged the drive into my computer, opened the file, and within a few minutes knew it would change the course of Alabama’s political history.
“You’d kiss me?” Bentley could be heard saying on the recordings. “I love that. You know I do love that.” He went on to describe—in explicit detail—touching her, pulling her “in real close,” and more. A lot more. “Hey, I love that, too,” he said.
As I listened to the roughly forty-five minutes of conversations between the two lovers, I cringed. I also felt a strange sense of sadness about what had happened and what was surely to come. Families would never be the same. The Bentley and Mason children would endure undeserved ridicule. And the state that I loved would weather yet another torrent of embarrassing headlines.
The next morning, I spoke on the phone with Mason for almost an hour. It was a roller-coaster conversation that made it abundantly clear that, in spite of her communications background and the obvious dangers of carrying on an intimate relationship with the Governor, there had not been much thought given to what they would say if they were ever caught red-handed.
Then came the excuses.
“Sometimes when you’re a woman working in politics,” she said, “you have to just let inappropriate comments roll off you like water off a duck’s back.” I stopped her from continuing and told her the recordings did not support that narrative. I could feel her anxiety growing.
“What should I do?” she asked. My advice was very simple: tell the truth.
It became clear that she was deeply conflicted. She did not want her children to hear what must be on the recordings. She did not want to be a front-page headline and the butt of every joke, like Alabama’s version of Monica Lewinsky. But she also did not want to give up just yet. Her unlikely rise from small-town television anchor to the most powerful political operative in the state had not come easy, and she was not convinced the ride was over.
She asked for an hour to think. I agreed.
She texted me several times asking for more details about the recordings. She said that she and the Governor were meeting about what to do.
One hour turned into several hours, and I texted her one last time saying I could not wait any longer to run the story, even though I wanted to include their side—whatever that could be.
Silence.
I hit “publish,” closed my computer, and sat back in my chair. My phone buzzed a few minutes later. It was a text from Rebekah Mason: “I’m sorry.”
Yellowhammer became the first news outlet to publish the complete audio recordings. The story was international news within the hour, and was soon accompanied by allegations of corruption, that the Governor was abusing his office and taxpayer dollars in part to carry on this affair. It consumed Alabama for weeks.
Who made the tapes?
As it turns out, Bentley’s wife of fifty years, Dianne, had grown suspicious of her husband. So while at their beach house one weekend, she hit “record” on her cell phone, set it down on a table, and went for a walk alone on the beach. The Governor took advantage of his sudden alone time by calling Mason. It was like a couple of high schoolers hiding their relationship from their parents, who just wouldn’t understand the depths of their endless love.
In the coming months, I broke numerous other stories on the Bentley-Mason saga. They had a secret safe-deposit box together. He’d sometimes ditch his security detail to meet her in complete privacy as state troopers were left desperately searching for the “lost” Governor. He’d dispatched a state helicopter to retrieve his wallet from his home in north Alabama and fly it to him at his beach house. We dubbed that scandal “#WalletCopter,” and Bentley defiantly admitted to it by saying, “I’m the Governor and I had to have money. I had to buy something to eat.” A year later he resigned in disgrace, cutting a deal with prosecutors to avoid jail time after multiple charges were filed against him.
Yellowhammer had helped take down a creepy Governor. I was a conservative Republican, but proud that we had helped rid our party of one of its corrupt leaders. We had made a name for ourselves as investigative journalists.
But slowly, over the course of 2016, my attention was being pulled back into what was happening at the national level. Little did I know how deeply I’d become embedded in that story.
Day after day I would make the drive from my home in suburban Birmingham to Yellowhammer’s downtown offices and marvel at “Teflon Don’s” seeming invincibility in the face of nonstop media fury. It was fun to watch, but the furor surrounding his candidacy didn’t fully hit home for me until the early fall of 2016.
Football season was under way and the Briarwood Christian School Lions, from suburban Birmingham, were slated to take on the inner-city Fairfield High School Tigers.
Just prior to the game, the Briarwood cheerleaders raised a banner for the football team to run through onto the field. MAKE AMERICA GREAT AGAIN—TRUMP THE TIGERS! the banner declared.
The seemingly innocuous play on words sparked an immediate—and furious—backlash.
“It’s ridiculous. To me, it’s an insult because I don’t like Trump and Trump doesn’t like my people either,” an African American Fairfield student told a local television station, which was breathlessly covering the supposed scandal.
“This should not be going down this close to me!” another student added.
In response to the blowback, Briarwood, a private, predominantly white school, immediately backed down. “Briarwood Christian School desires to publicly apologize for any understandable offense caused by the sign used during a recent football game,” they said in a statement released to local media. “Above all we desire to seek forgiveness of any who were offended.”
This was a silly banner, not an endorsement of a political campaign. To me, the whole fiasco looked like the scourge of political correctness that Trump had been railing against, and the faux outrage over the banner compelled me to personally incentivize schools to stand up to the PC police. I relished being a political troublemaker.
At the time, the Clinton campaign was struggling to explain why Secretary Clinton had set up a private email server to house her communications—including some of a classified nature—while serving as Secretary of State. Additionally, tens of thousands of the emails had inexplicably been deleted, apparently lost forever. So, maybe just to be a malcontent, I offered to donate one thousand dollars to the first high school football team who ran through a pregame banner that said HILLARY WOULD DELETE THIS BANNER IF SHE COULD.
The episode drove local media coverage for several days, and was generally amusing to me, but it also came at a time when I was starting to really consider what the 2016 presidential race meant for the country. I stumbled across a pseudonymous essay titled “The Flight 93 Election” in The Claremont Review of Books, published by the conservative think tank the Claremont Institute. It was driving a lot of conversation online and I wanted to see what all the fuss was about.
2016 is the Flight 93 election: charge the cockpit or you die. You may die anyway. You—or the leader of your party—may make it into the cockpit and not know how to fly or land the plane. There are no guarantees.
Except one: if you don’t try, death is certain. To compound the metaphor: a Hillary Clinton presidency is Russian Roulette with a semi-auto. With Trump, at least you can spin the cylinder and take your chances.
That struck me as roughly correct. Yes, America is bigger than any single election, and no, I didn’t think we had al-Qaeda terrorists in the pilot’s seat in Washington. But I was deeply concerned about the country’s trajectory. I was—and am—a conservative. But, as I demonstrated during the Bentley case, I was more than willing to see the faults in the Republican Party or its leaders. What bothered me the most in 2016 was not just a dispute between political parties, or ideologies, but something larger.
Like many Bernie Sanders supporters who still hadn’t gotten behind the Democratic nominee, I thought Hillary Clinton was a corrupt member of America’s ruling class—the “masters of the universe,” as Jeff Sessions liked to call them. This included leaders of both parties in Washington, D.C., who made all sorts of promises, got richer and more powerful as they went along, and never actually delivered for the people they were supposed to represent.
As I snaked my way up Highway 280 from my house to the office, I considered the moment in American history, and whether I was doing enough myself. Did the challenges facing our country—on which I believed Donald Trump was generally correct from a policy perspective—supersede the significant character concerns I had with him as a human being?
This was a question that Senator Jeff Sessions had clearly wrestled with to some degree as well. I’d asked him about it during an interview on my radio program.
“I think good people in Alabama are concerned about [Trump’s character and integrity],” he had told me. “I’ve tried to think about it, and none of us are perfect, but … anybody who wants to be president needs to conduct himself … as a person of character. He does seem to have a good family … the kind of people that must have had some good values when they were raised. He doesn’t drink. So I understand and I’m hearing that, and I appreciate the concerns.”
As I drove toward my office and thought about whether I wanted to have a role in the 2016 race, I decided to call Senator Sessions on his cell to get his advice.
Although many people have taken issue with some of his positions on various issues, particularly his hard-line stance on immigration, I knew him as a decent and honorable man. My wife, Megan, and I had gotten to know him and his wife of forty-seven years, Mrs. Mary, over long dinner conversations. They loved their family. They weren’t engrossed by the trappings of power. Jeff Sessions had a reputation for wanting to do what he believed was the right thing—to the point that his Senate colleagues called him “the Boy Scout” behind his back. Sometimes this was said with genuine respect. Other times it was said in frustration.
I told him that I thought I might want to take a leave of absence to join Trump’s campaign for the home stretch—to do my part, whatever I could. I could hear the excitement in his voice.
“If nothing else, it’ll be a once-in-a-lifetime experience,” he said. “And if he wins, who knows what could happen. I’m happy to call and set it up.”
As it turned out, the campaign was excited I was willing to come on board and made me an offer to come join right away as a communications adviser. With the opportunity now in front of me, there was no way I could just sit back and complain any longer. My wife and I discussed it, prayed about it, and decided that if there was an opportunity for me to have any influence, even a small one, on the campaign, on the country’s future—on Trump himself—it would be worth the effort.
Days later, I announced I was taking a leave of absence as CEO of Yellowhammer and moved into an apartment in midtown Manhattan. I was officially aboard the Trump train. I didn’t know yet whether it would run off the tracks and go down in a blaze of glory, or steamroll the Clinton machine on its way into the history books. And nobody else did, either, not even the candidate himself.