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The Risky Business of Speaking for President Trump

5/23/2018

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CreditPhoto illustration by Christian Northeast. Source photographs: Getty Images.

It was getting late on a Wednesday, and by 2018 standards the evening’s news cycle felt almost serene. The only “breaking news” of the moment was about Dr. Harold Bornstein, Donald Trump’s doctor of 35 years, who had told NBC that the president’s bodyguard led a “raid” on his office and hauled away his medical files for “the healthiest individual ever elected to the presidency,” as Bornstein previously pronounced him. But that story was now a day old, a musty chyron at this point.

Then, at about 9:30 p.m. on the East Coast, the president’s newest lawyer, Rudy Giuliani, went on Fox News and belly-flopped himself into the news Jacuzzi. On Sean Hannity’s show, the former New York mayor — now, somewhat improbably, a presidential attorney — announced that Trump had in fact reimbursed another of his lawyers, Michael D. Cohen, for a $130,000 payment that Cohen made to Stephanie Clifford (or “some Stormy Daniels woman,” as Giuliani referred to her on “Hannity”). Giuliani’s disclosure seemed to flatly contradict a claim that Trump had made about the Clifford payment — thus making it very likely that the commander in chief had been caught in yet another “false or misleading claim,” or “lie,” to use the less euphemistic word.

It also meant that someone named Hogan Gidley would have another chance to prove himself worthy in Trump’s flat-screen universe.

Who is Hogan Gidley? Or “What’s a Hogan Gidley?” as Senator Lindsey Graham asked of Senate aides after Gidley, a deputy White House press secretary, accused the South Carolina Republican in March of supporting an immigration policy “that sides with people in this country illegally and unlawfully.”

In real life, a Gidley is an unmarried 41-year-old from South Carolina whose West Wing office is stocked with bottles of Muscle Milk. He is a mop-haired Republican flack who has bounced around government and campaign jobs and dresses better than most political operatives do, a fact he attributes to his mother’s previous work as a high-end accessories buyer at an apparel store. I would occasionally run into Gidley as he worked on long-shot presidential campaigns — Rick Santorum’s in 2012, Mike Huckabee’s in 2016. He conveys the smooth and slightly cloying folksiness of someone who has been around a lot of politicians. He was pleasant enough to deal with, if not always particularly plugged in or — for that matter — in great demand among the better-funded “establishment” Republicans like Jeb or Mitt. That all turned out to be more than fine for Hogan Gidley, because look where he is now: on TV, defending the president.

To speak for any White House is a delicate exercise even in the best of circumstances. You’re trying to relay a president’s message while also disseminating little actual information; you’re taking abuse from the press while trying, theoretically, to assist them; you’re selling the president’s agenda while not stealing too much of his spotlight. Also, be careful: Your words can move markets, offend entire religions and trigger international incidents — or, in this case, trigger the “audience of one” tuned in to his surrogates from upstairs.

But speaking for President Donald J. Trump presents a particular set of challenges. In Gidley’s case, it means saying things that Gidley might normally not be inclined to say, or defending things he might normally have a hard time defending, or offending people in ways that might defy his otherwise pleasing nature. But Gidley is willing to do it, and that, perhaps more than any of his other qualities, is why I had become fascinated with him.

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CreditPhoto illustration by Christian Northeast. Source photograph of Gidley: Associated Press. All other source photographs: Getty Images.

On the night of May 2, Gidley had a prescheduled interview with Shannon Bream, host of “Fox News @ Night,” at the 11 p.m. hour. This made him the White House’s first line of defense about the changing Stormy Daniels story. Gidley had natural gifts to draw upon. His manner is eager and aggressively aw-shucks, reminiscent of those dumbfounded underling characters from military-themed sitcoms of the ’60s (“F Troop,” “Hogan’s Heroes”). Before entering politics in 2004, he worked as an on-air personality at a TV station in Little Rock, including a stint as a local weatherman. He clearly likes being on TV and is possessed of a polished on-camera presence, customized earpieces (molded especially for each ear) and a repertoire of syrupy banter and evasion skills well suited to times like this.

In the Bream interview, Gidley leaned on the crutch of referring “anything on this matter” — the Clifford payment — “to the president’s outside counsel.” He told Bream that “we’ve addressed this many times,” even though “this” had taken a 180-degree turn earlier in the evening, courtesy of Giuliani. Gidley would remind Bream that he could not speak about “ongoing litigation.” The one hiccup was that on the second and third references he said “ongoing legislation,” but he still managed to maintain his air of complete authority. Gidley tried to pad his stonewalling by fashioning a “sorry-I-just-work-here, ma’am” tone of unhelpful regret in response to Bream. This is one of his go-to moves.

“Again, its ongoing legislation, I can’t speak to it,” Gidley said to Bream. “I’m not an attorney. I just work at the White House.”

In the two years since Donald Trump first upended our politics, a generation of spokespeople have hitched their careers to him, with mixed results. They have become objects of outsize exposure, commensurate with the fuss and emotion this president attracts. They can acquire a significant public profile of their own — and can suffer significant collateral damage. Sarah Huckabee Sanders and her predecessor, Sean Spicer, might be simultaneously the most famous and infamous press secretaries ever to stand at the White House lectern. Hope Hicks was unquestionably the most fixated-over White House communications director in history, rivaled only by Anthony Scaramucci during his 10 days of hellfire last summer. Kellyanne Conway, a longtime G.O.P. pollster, caught on as Trump’s campaign manager two summers ago and has since been known as his most ubiquitous defender/enabler/dissembler. The president’s spokespeople are easily nicknamed (Spicey, the Mooch) and come with their own ready-made “Saturday Night Live” treatments, side dramas and caricatures, all bound somewhat to the same theme — that speaking for Trump is an almost absurdist proposition.

In previous White Houses, press offices functioned as far more predictable entities. They could be frustrating and rarely edifying to deal with, but no one would expect otherwise — in the same way that no one would expect to be entertained on a trip to the dry cleaners. In my experience, these operations generally worked according to a default dictum of “Do no harm.” I recall a story from 2004, after President George W. Bush popped into a Roosevelt Room celebration of his communications team to offer his thanks. He singled out Scott McClellan, his bland and robotic press secretary, for a special tribute. “I want to especially thank Scotty,” Bush said. “I want to thank Scotty for saying” — he paused — “nothing.”

“Nothing” would be insufficient in the service of Trump. That partly explains his appeal to many of his supporters, who appreciate that he does not speak in the same lobotomized, on-message way as other politicians. Trump loyalists perceive him to be “plain-spoken” even when he says things that are plainly untrue, or that would sound outrageous if uttered by someone not afforded the same “let Trump be Trump” indulgence. The 45th president has proved, again and again, that he is a sui generis character whose appeal is predicated more on his own colossal selfhood than on any definable set of ideas or positions.

One contradiction of the Trump phenomenon is that even as his spokespeople enjoy and suffer through enormous exposure, the president’s Twitter habit — by far his most powerful communications tool — renders them less necessary than ever. Still, Trump places high value on his proxies and expects them to talk more or less as he does, even if this might include advancing dubious claims and crossing certain lines of decorum. There is no better way to win favor with the boss in this White House than for him to see you on TV promoting and defending him, the more adamantly the better. As a result, the job inevitably carries significant risk for the spokesperson’s own reputation.

This risk becomes especially acute when Trump’s ambassadors are called upon to peddle “alternative facts,” as Kellyanne Conway once memorably put it. She uttered those words in defense of Spicer, who at the behest of the newly sworn-in president had stepped into the briefing room on Day 2 and insisted that Trump’s “was the largest audience to ever witness an inauguration, period.” Overhead photos showing Trump’s crowd side by side with Barack Obama’s readily disproved this. And Spicer thus became the fastest White House press secretary to blow up much of his own credibility, period.

Compounding the problem has been the torrent of leaks from West Wing staff members and hangers-on, which has placed the White House’s internal dysfunctions and hypocrisies on constant display. Case studies can be done — and probably have been — on why people disclose privileged information to journalists and what a high rate of such might say about an institution. But the best way to summarize it for our purposes is that leakiness in a White House can reflect a undisciplined and paranoid environment where self-preservation can outweigh loyalty, including (or especially) to the president himself.

As I sat at my desk writing this in mid-May, the top stories of the moment all testified to how porous this White House had become. That morning in a communications meeting, Kelly Riddell Sadler, a special assistant to the president, dismissed a mention of Senator John McCain, who is battling brain cancer, by supposedly saying that McCain’s opinion (in this case, his opposition to Gina Haspel’s nomination as C.I.A. director) did not matter because “he’s dying anyway.” Of course everyone instantly learned about this because someone in the meeting leaked that attempted “joke,” and it was all over the news by that afternoon — competing with a story (also leaked) that Trump exploded at Homeland Security Secretary Kirstjen Nielsen in a cabinet meeting the day before, and another story (leaked the day before) that Haspel had discussed withdrawing her nomination with the White House. In a meeting the next day, Sanders admonished her team of sieves and added for good measure that “I’m sure this conversation is going to leak, too,” which naturally ensured you-know-what. (ABC News cited “multiple senior White House officials” in reporting Sanders’s scolding, while Jonathan Swan of Axios followed with a fuller account of the leaked outburst “according to five sources in the room.”)

With its proclivity to leak, zigzagging of messages and volatile principal, the press and communications apparatus of this White House has been a baffling production to say the least. The situation presents a dilemma for any would-be Trump proxy. Kellyanne Conway, whom I visited in her top-floor office in the West Wing, distilled the problem to this: “There have been relatively few people in the press corps who have really stopped to get to know the president,” Conway told me, “and the way he makes decisions and his thought process.” In other words, if reporters feel misled or lied to by this White House, maybe they should look in the mirror or work harder. People either “get” Donald Trump or they don’t, she said.

Conway, who is 51, seems fond of pointing out that she is one of the older members of the White House and is thus availed of a more seasoned perspective than her colleagues. She also has the benefit of having survived in Trump world since being hired as his campaign manager in the summer of 2016, and is now a counselor to the president. This places her well ahead of the curve at a White House that has seen a whiplash rate of churn; nearly half of ranking senior advisers have already turned over, according to a Brookings Institution survey (released in March, so the figure is now higher). “I basically have never been fired or forced out,” Conway said. She suggested that many of the more dubious accounts of the White House are coming from people who are untrustworthy. “You still trust them as sources, I don’t know why.”

However things end up for Conway in the White House, she is a made woman in the House of Trump. What began to interest me more was the younger cohort of spokespeople with shorter résumés to fall back on and, in many cases, longer careers ahead of them. What if any is the long-term risk of contagion for working at such a divisive enterprise? It led me, again, to the question: What’s a Hogan Gidley?

“Delivering a message for a White House is the pinnacle,” Gidley told me on a Friday afternoon in late April. “Not the pinnacle monetarily, but the pinnacle of what you can do from a love-of-country standpoint.”

We were in his cramped work space in “lower press,” just off the briefing room. He was snacking from a large bag of reduced-sugar Ocean Spray Craisins. Much of our conversation early on had centered on his hyperregimented diet and exercise habits. A former varsity tennis player at the University of Mississippi, Gidley is a health-and-fitness freak who weighed 140 pounds in high school and weighs 177 pounds now (he weighs himself almost every day). He eats every two hours, works out five times a week and focuses on specific body parts each day: his back and abs (Monday), chest (Tuesday), legs and abs (Wednesday), arms (Thursday) and shoulders and abs (Friday).

When speaking about his job, Gidley is quick to marvel at the day-to-day spectacles he is blessed to witness. The day before, for instance, he attended the swearing in of Mike Pompeo, the newly confirmed secretary of state; it was, he gushed, a “really cool moment” and indeed a “really big high.”

On this particular Friday (a shoulders-and-abs day), he was preparing to attend some pre-parties before the White House Correspondents Dinner. For the second year in a row, Trump planned to skip the ordeal in favor of a rally, this one in Michigan. He would spend a good part of his speech attacking the press, or “enemy of the people,” as he previously dubbed the Fourth Estate. Even so, many of Trump’s White House aides and spokespeople would be attending the soiree to share a toast with the enemy.

Gidley would be among them, and he told me that he very much enjoys seeing the many media friends he has come to know over the years. He dropped a few names (“I’m friendly with Stephanopoulos”); mentioned that he used to love watching “Hardball”; noted that he has been a frequent guest and used to be a paid contributor on CBS News; and volunteered that he once went on “Real Time With Bill Maher.” Gidley describes his own politics as “Christian conservative populist.” I asked him if he would count himself among the 51 percent of Republicans in a Quinnipiac survey who said they agreed with Trump’s “enemy of the people” description of the press. He demurred. “I don’t know that I would agree with the characterization,” he said sheepishly. “I do think the press does a massive disservice to the people.” He made a point of telling me he is “not a bomb-thrower.”

This was a different tone from the one Gidley struck on TV a couple of months earlier, arguably his breakout moment as a Trump commando willing to throw bombs. In February, on the morning after the Department of Justice announced that a grand jury had returned indictments against 13 Russian nationals and three Russian companies for seeking to disrupt the 2016 presidential election, Gidley — then five months into his White House tenure — was sent out to appear on a weekend edition of “Fox & Friends.”

“There are two groups that have created chaos more than the Russians,” Gidley said. “And that’s the Democrats and the mainstream media.” If he was watching, Trump would no doubt have been pleased. Russia certainly was, as evidenced by the fact that RT, the Kremlin-backed propaganda tool, tweeted Gidley’s words shortly after he uttered them. In fact, RT tweeted three different versions of the statement within minutes.

Not so pleased were a fair number of my colleagues in the “mainstream media” who registered their disgust via Twitter (“either an embarrassing misstatement by a White House official,” wrote Zeke Miller of The Associated Press, “or a stunningly unsupported charge against fellow citizens”). At risk of betraying my mainstream-media bias, I, too, was among the outraged. The media always offers an easy target for politicians, especially Republicans. But this was one of those egregious circumstances when you question whether we’re witnessing a basic scrambling of loyalties. It’s hard to be neutral when it comes to something that so offends the simple principles of what we’re doing here — whether as journalists, White House officials or Americans. “Good God almighty,” Gen. Michael Hayden, the former director of the N.S.A. and the C.I.A., tweeted in response to a Fox News tweet plugging Gidley’s comment.

The episode loomed large in my mind as I tried to divine just what a Hogan Gidley was. Had it just been a throwaway line, or did it speak to a larger rite of passage for anyone who wants to represent Trump? At the very least, Gidley showed that he was willing to do what it takes to please the president in a hot moment.

Soon enough, my anger subsided, and so did the umbrage — and the tweet storms, and all the “pickup” Gidley’s remark received that weekend; also, the attaboys from some of Gidley’s like-minded friends and colleagues, which he very much appreciated. And then the rocket passed, the heat burned off and we were all onto the next thing.

I had informed Gidley that I was writing an article, generally, about what it is like to speak on behalf of Donald Trump. I said I was interested in him in part because he is less well known than the others. About halfway through our second meeting, I asked Gidley how he would define “fake news.” He paused.

“Let’s stop for a second here,” he said. “Where are we on the attribution scale for this thing?” I told him we were on the record. Why shouldn’t we be? I said. He was, after all, a White House spokesman. This arrangement would seem self-explanatory, except the relationship between “spokespeople” and “journalists” has in many cases come to assume anonymity as the default. This assumption approached a comical nadir a few months earlier when Gidley walked to the back of Air Force One to take questions from reporters who were traveling with Trump to and from an event in Utah. Gidley made it clear to the traveling press that he would answer questions only if he were not quoted. The reporters protested. “I understand that, you have a job to do, and so do I,” Gidley said.

Justin Sink, a reporter for Bloomberg, replied: “You’re not doing your job. Your job is literally to take questions from us. That is the whole point of this. You can release paper statements if you want.”

Gidley told me that he wanted to speak “on background.” I shook my head. He appeared taken aback by my lack of accommodation. He started to protest but then cleared his throat and rambled through a hard-to-follow answer. “Fake news is not just news that is incorrect or inaccurate, it’s also news that’s inherently biased in its presentation,” he said. “A lot of times when you have reporters” — he throws up air quotes while saying “reporters” — “they give you information. Bias words, they’re your opinion, also in Twitter feeds, snarky, mocking the president and first lady. Don’t pretend you’re straight news reporters.”

Gidley went on for a while. He threw out examples of the kinds of things “journalists” — more air quotes — might say on TV that could betray a point of view. He did not cite specific reporters or examples, but no doubt he was correct in certain cases. After a few minutes, he seemed to catch himself. “Sorry, a little tirade,” he said.

I reminded Gidley how, on the morning after the Department of Justice charged Russians with engaging in “information warfare” against the United States, he compared the “mainstream media” unfavorably to Vladimir Putin’s regime. “I’m kind of glad you brought that thing up,” he said, seeming to suggest that he knew the comment still lingered over him.

“I don’t want to go into a thing about defending the comment itself,” he said. “This Russia thing has been covered. I can give you countless examples, ridiculous examples, over and over and over again. To create a narrative is too weak of a word, to create a boogeyman. ...” He kept complaining about the media’s efforts to “tether this president to Russia.” He seems to like the word “tether,” which always makes me think of that old gym-class game, tetherball. Players hit a volleyball attached by a rope to a pole, back and forth, until eventually the ball and rope get wrapped around the pole and the game ends, which is something like how conversations like this usually go.

“If you could do it again,” I asked, “would you have said that?”

I had no idea what his answer would be. My guess is, Gidley is a little like Trump in that he enjoys the showmanship aspect of being a bomb-thrower, or playing one on TV, but not so much the face-to-face discomfort of offending someone in a conversation, where he would just rather banter and maintain “good chemistry.”

“Yeah,” Gidley said in response to my would-you-do-it-again question. “I might have added more alliteration to make it more memorable.”

Regardless of how he really felt, Gidley was not about to admit to any regrets on the record — not a good look in Trump world. We went back and forth for a while until tetherball ended.

On the day after Giuliani’s interview with Hannity, I went to watch Sarah Huckabee Sanders at her afternoon briefing. By then, Trump himself had tried to clean up the Rudy situation (itself an attempt to clean up Trump’s Stormy situation), saying that his new lawyer will “get his facts straight.” Jonathan Karl of ABC asked Sanders how anyone could trust or believe anything the White House says, given how “the president and the White House show what appears to be a blatant disregard to the truth.” Many Americans had already made determinations about this. A solid majority — 61 percent — said they believe Trump “tells the truth only some of the time or less,” per an NBC News/SurveyMonkey survey. As of early May, Trump had made over 3,000 “false or misleading claims” since taking office, an average of 6.5 per day, according to a tally in The Washington Post.

“We give the very best information that we have at the time,” Sanders replied.

I visited Sanders in her West Wing office, upstairs from the briefing room. She exhibited a level of vulnerability, possibly nervousness that softened the homespun sneer she can sometimes exhibit in her briefings. At the Correspondents Dinner a few days earlier, the comedian Michelle Wolf unleashed a withering attack on Sanders (“She burns facts, and then she uses that ash to create a perfect smoky eye”), who was sitting a few feet away while TV cameras captured her wincing reaction.

When I asked her how her weekend was, she laughed. “There were good parts and bad parts, I guess,” she said. She told me she introduced herself to Wolf backstage before her routine. “She didn’t have a lot to say,” Sanders said. “It wasn’t incredibly warm.”

Sanders told me she tries to remember what really matters in life. She pointed out that none of what we were talking about was going to “impact that family in Ohio” trying to pay their bills. I mentioned to her that every White House operative or presidential candidate likes to invoke the mythical “family in Ohio.” Their point is that the media concerns itself with trivial things that “real Americans” don’t really care about. Sanders left out the part about the family in Ohio’s sitting around their kitchen table — and also that her boss had been tweeting that week about how Kanye West said something nice about him.

Twenty minutes or so into our conversation, Sanders started stressing to me that the news media play an “incredibly important role” in a democracy and that a free press “holds great responsibility.” I figured the “but” would come soon enough, and sure enough: “But,” she said, “there is a responsibility to be accurate.” Totally agree, I said. We absolutely do have a responsibility to be accurate. “Do you?” I asked.

“I, I, I do,” she said. “I will always do everything I can to give the best and most accurate information at the time that I can.”

What does that mean?

“What’s true on Monday in terms of a process decision may change by Friday,” Sanders said. “And I can’t always know that things will be different.” It often does not take that long for a “process” to evolve, I said. Sometimes a 5 a.m. tweet generated from the White House residence amounts to a “process” in Trump’s presidency. Or an old friend of Trump’s who just joined his legal team might go to dinner and jump on Fox News for a few minutes, and then the “process” jumps again. Like many of her White House colleagues, Sanders is quick to suggest that some of the criticism the Trump White House has received is a product of a biased press. I replied that a lot of what we’re talking about here is a matter of simple fact, not ideological bias; the media’s only bias should be toward what is truthful, nothing more.

“It certainly bothers me,” she said of the “liar” rap. “Because one of the few things you have are your integrity and reputation.” She added that “there’s a difference between misspeaking or not knowing something than maliciously lying.”

No one would argue that a person’s integrity isn’t of paramount importance, I said. But I asked Sanders if there is a danger in linking your integrity to a president who might not always be known for accuracy. There have been many instances where the president has not told the truth, I said.

“But you’re asking about me,” Sanders said, not challenging the premise.

True, I said, but she has to speak for him. I asked the question another way: “Is it possible to be factual if you’re speaking for someone who is trying to make a point that is not factual?”

“Uh, I don’t know,” Sanders said. “I’m not following totally.” But it was important for me to remember this: Donald Trump is president. “And I think one of the biggest reasons Donald Trump is president is because he is not scripted, not following your conventional playbook.” He is “the ultimate disrupter,” and people find his plain-spoken style “refreshing.” They like that he is unfiltered, she said, like that he “tells it like it is.”

Sanders’s assistant popped her head in about something. “I may have to go, so don’t kill me,” Sanders said, grabbing a Hot Tamale candy from a large jar of them on a conference table. She stood up while peeking at a bank of muted TVs, as if checking to see if it were safe to leave.

“Am I going to hate this story?” Sanders asked as she walked me to the door. This was also the first thing she said to me when I walked in. She laughed as she said it, something between plaintive and resigned, and she ended on a playful suggestion.

“Make Hogan look bad and me look good,” Sanders said.

Mark Leibovich is the chief national correspondent for the magazine.

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