On the frigid morning of February 16, 2017, Mike Dubke sat in front of the Resolute desk, facing Donald Trump. “Tell me a bit about yourself,” the President said. Dubke obliged, but after a few minutes Trump cut him off. “All right,” Trump said, “so what do you think about a press conference? Do you think I should do a press conference?”
Six days earlier, this scene would have been all but unimaginable for Dubke. It had been a standard Friday at Black Rock Group, the Alexandria-based public affairs firm that Dubke helped found. Dubke had just gotten off a conference call and was looking forward to a family ski trip the coming week. And then Sean Spicer called.
Spicer was then juggling the dual roles of White House press secretary and communications director. He wanted to speak to Brian Jones, a partner at Black Rock who was well-regarded among Republicans, most recently for being an adviser to Chris Christie’s brief 2016 campaign. Spicer asked if he was interested in being the next White House communications director.
Jones decided against it; he had two young kids, and he knew what those hours would look like. But before he called Spicer back, he turned to his business partner, Dubke. “Are you interested?” Jones asked, only half-joking.
Dubke shrugged and—as one does when offered a shot at coordinating messaging for a White House ensconced in PR nightmares like a disastrous travel-ban rollout and a national security adviser resigning in disgrace—said, “Eh, why not?”
So it was that Dubke—a tall and cheerful 47-year-old with an aesthetic familiar to any actor ever cast as a Pop Warner football dad—found himself in the Oval Office, advising Trump on his impromptu plan to meet the press. He suggested the President bring in policy experts, look at the calendar to see when might make sense, and then drill down on one particular issue. The kind of advice any flack might give.
Trump cut him off again. “No, I mean today,” he said. “I think we should do a press conference today.”
The remainder of Dubke’s interview was thus spent looking on as policy folks prepped the President and ushers set up the East Room, and learning that the harder Vice President Mike Pence punches you on the arm, the more he likes you. (That first punch was light, Dubke says, but they’d only just met.)
And then the press conference, Trump’s first as President, commenced. The freewheeling session featured such vintage Trumpisms as “the leaks are absolutely real. The news is fake,” and “Russia is fake news.” Dubke stood against the wall, stone-faced in the cameras’ line of fire, while his phone buzzed incessantly with texts. Asked one friend: “What the hell are you doing at the White House?”
Spicer called around 8 that night with an offer: Dubke would start the next day.
The lead-up to Dubke’s interview and the interview itself—a chain of events marked by whims and happenstance and even leaks—should’ve been warning enough about the months to come. Dubke made it all of 103 days before resigning on May 18. And in two hours of recent interviews with Washingtonian, he spoke about the frustrations and financial disclosures and unforeseen health issues that defined them.
His reflections offer a broader window into just how slipshod this administration’s operations can be, how leaks, especially early on, crippled the press shop, as well as a West Wing in which a select few were hell-bent on bolstering their own names at the expense of the White House as a whole.
“The thing about Dubke is you’re never questioning the quality of work. He’s a smart tactician and an unbelievably stand-up individual,” Spicer says. Perhaps his biggest liability, though, in a White House that incentivizes on-screen savvy, was that “Mike wasn’t looking to become some TV star.”
Dubke could never quite shake the swamp narrative that took hold when he joined the White House. He fit neatly into the so-called establishment—his two firms, Main Street Media Group and Black Rock, have long counted American Crossroads, the Karl Rove-led behemoth of a super PAC, among their clients. The Rove link made Dubke an easy target for campaign folks inside and outside the White House—even though, as Dubke puts it, he could “probably count on one hand” the number of times he and Rove have interacted. Quickly came the unnamed sources castigating the hire: “How does this help serve the President’s interests?” one “Trump insider” asked the Washington Post. “It serves the interests of Reince and Sean, but I don’t see how it serves the President’s interests.” The chattering class, though, deemed it a signal of Trump’s willingness to get serious, to branch outside his ragtag circle of loyalists in favor of an establishment counterweight.
Yet with no campaign ties, and having never worked for the Republican National Committee, Dubke entered the White House tribeless. Those were the dividing lines, at least in the comms and press shops. “Those camps got along well, but they were definitely camps,” Dubke says. “You’ve worked in the trenches with folks at the RNC, you’re going to know your people there quite well. Same thing with the campaign. You’ve been in the trenches with these folks for months fighting a very hard presidential campaign; you’re going to know these folks very well.”
Which is to say Dubke didn’t have as natural a constituency as most onlookers imagined. He claims there were “benefits” to this, in that he could “easily flow into both worlds.” But the reality is that few staffers felt they owed Dubke their loyalty, and in a work environment whose social politics were charged with the volatility of a high school cafeteria, that was, well, not great. “He was destined to fail,” says one former Trump adviser. Adds a source close to the White House: “I literally never heard anyone ask, ‘Is Dubke onboard with this?’”
Nonetheless, Dubke says one of his early efforts was to unite the masses. “I wanted everyone to trust each other.” The first week of April, as the symbolic 100-day mark loomed, he organized a brainstorming session in an Eisenhower Executive Office Building conference room on how to best sell the President’s agenda. “I had this thought that if we brought in all the junior staffers and the mid-level staffers and the senior staffers from communications and press, and we all worked together, everyone would feel like they were all part of the team,” he says.
Less than a week later, a Politico story on the meeting popped. It featured detailed complaints about Dubke’s leadership, sourced to six anonymous White House officials—roughly 20 percent of the gathering’s attendees. Today, seven months later, that piece still bothers Dubke. “In my mind, it was ridiculous, and I think what it was, really, was probably a way for some junior staffers to make themselves feel important, by telling a reporter about a private meeting in the White House,” he says. “I was just upset.” He says he had an idea of who the leakers were, and confronted some of them, but felt he didn’t have “enough hard evidence” to fire them.
“I hate to say it,” Spicer says of their attempts to plug the leaks, “but it became futile.”
Yet Dubke says he regrets not firing anyone, or at the very least, moving some people outside of the West Wing, even if he didn’t have concrete proof of guilt. He drove home to Alexandria that night to talk about it with his wife. “I think I know. I’m almost positive,” he told her, “but I’m not 100 percent sure. Do I want to ruin somebody’s reputation and somebody’s livelihood?’
“If I had one regret from my time there,” he says, “it’s that I wish I had done that in a couple of cases.”
Dubke maintains that the constant crush of leaks often kept his team from strategizing on long-term messaging, ostensibly the main function of the communications department. The combination of starkly defined factions and stubborn personalities meant that every issue, it seemed, was litigated in the press; for every “senior administration official” touting the White House’s unity behind an executive order or policy proposal, there was another eager to sow whispers of division.
Take steel tariffs, for instance: in April, Trump signed an executive order that called for the Commerce Department to investigate the economic impact of steel imports into the US, with the eventual goal, perhaps, of slapping on a tariff. “It was one of those where there continued to be leaks about one side or the other in order to force the President to make a decision, maybe before he had heard all the arguments,” Dubke says, an implicit reference to what he calls the “water-and-oil” pair of National Economic Council director Gary Cohn and National Trade Council director Peter Navarro. “That fight continues.”
Also to blame for the lack of long-term messaging: Dubke’s workspace. His office was in Upper Press, ground zero of the White House press corps. “In hindsight, I think I would’ve put my office up on the second floor,” he says. “A lot of times, I’d get a knock on the door, and a reporter’s asking me a question because they can’t get ahold of Sean…It’s hard to focus and get your work done when you’re constantly being interrupted like that.”
Leaks, bad real estate—in Dubke’s view, these are all reasons why, for instance, tax reform—Trump’s last hope for a major policy victory before midterms—limped out of the gate. “I feel like some of the messaging on tax reform, really, it needed…there could’ve been some more messaging coming out of the White House or the Treasury Department in terms of what the goals are, why it’s important to cut our tax rate from 35 percent to 20 percent,” he says. “That’s one example of where I think we probably didn’t do as good a job.”
It’s an admission that brings into sharp relief the ways in which this White House is often its own worst enemy. The counterfactual, of course, is difficult to envision: if the comms shop had engaged in an early, robust messaging strategy with regard to tax reform, would it have reached the floor by August, as Treasury Secretary Steve Mnuchin had originally hoped? Probably not. But December? Possibly. If anything, it would have helped clue in the average Trump supporter to a White House goal that, until now, they likely didn’t know existed.
So, yes, Dubke has some regrets. But he says a lot of good came out of his “front-row seat to history,” too, however brief the view. Despite having no immediate allies coming in, he got close to Spicer—mainly, he claims, because neither of them “had a big ego.” “There was a level of trust between the two of us. I’ve got his back; he’s got my back.” It’s difficult for him to explain it beyond that, because as with all great friendships, “it just kind of happened.” He counts Sarah Sanders as a friend, too. Hanging in his office at Georgetown University, where he now works as a politics fellow, is a photo of the two them walking and laughing outside the White House. (It should be noted that a Georgetown staff member put the photo there, not Dubke, but he still says they’re friends.)
But what did Dubke think of his other colleagues, such as Omarosa?
He pauses for a long time. “I think she’s got a lot of shoes,” he says. I ask him why he says this. “Because she’d leave them all over the White House.”
He clarifies: “We had this desk in Upper Press that was a temporary desk for somebody who didn’t work in the West Wing. But she’d come over for meetings and other things. And her shoes were always there, different pairs. So we had a collection of Omarosa’s shoes.” It was a potential safety hazard, White House staffers agreed, so they had to be “kicked under the table.” Dubke is unclear on whether this meant Omarosa was walking around barefoot, or perhaps just liked to wear different pairs at different parts of the day. “I’m not sure that I ever witnessed the changing of the shoes,” he says, “just that the shoes that were left there were Omarosa’s shoes.”
Alas, the friendships and reality-star sightings weren’t enough to keep Dubke around. Reports this summer suggested he resigned because of an inability to breach and break bread with Trump’s inner circle. That’s in some sense true. But Dubke says that mainly the job wasn’t worth selling off his businesses—”all of what I’ve built over the last 25 years”—as the Office of Government Ethics demanded. And then there was a visit to his doctor the month before, when he learned that his blood pressure was “way up…which my wife wasn’t too pleased about.” The doctor put him on medication.
Thus Dubke entered the Oval Office on May 18, resignation letter in hand, just over 100 days after his improbable arrangement of that first press conference. (He offered to stay into June as Trump wrapped up his first overseas trip as President.) He says he and Trump had a “very candid conversation” about the “level of frustration I had that things weren’t progressing as quickly as I thought that they could.” He won’t get more specific than that, but says one of the things he liked about Trump was that he “never felt” he couldn’t speak his mind. All told, he says he “appreciated” his relationship with this President.
And that’s part of what made leaving the Oval and walking to West Executive Boulevard and getting in his car to head home so complicated. There was disappointment, he says, “in the sense that I felt like I was doing good, and I felt like I was making a difference.” There was remorse. “When you walk away from a situation in which you are really in the trenches with your colleagues, and you step away from that…I did have some remorse after I left,” he says. “Because I felt like I left them behind.”
But now, sitting at his desk at Georgetown, blood pressure under control, with a meeting soon on behalf of those insidious Rove-tied firms, he admits there was another emotion, too: “A bit of relief.”
Elaina Plott joined Washingtonian in June 2016 as a staff writer. She has written about her past life as an Ann Coulter fangirl, how the Obamas changed Washington, and the rise and fall of Roll Call. She previously covered Congress for National Review. Her writing has appeared in the New York Observer, GQ, and Harper’s Bazaar.
