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Sean Spicer has the craziest job in the Trump administration

Some of Canada’s top political communications experts on what it must be like trying to manage Donald Trump’s message
Press Secretary Sean Spicer delivers a statement while television screen show a picture of U.S. President Donald Trump’s inauguration at the press briefing room of the White House in Washington U.S., January 21, 2017. (Carlos Barria/Reuters)
Press Secretary Sean Spicer delivers a statement while television screen show a picture of U.S. President Donald Trump's inauguration at the press briefing room of the White House in Washington U.S., January 21, 2017. (Carlos Barria/Reuters)
Press Secretary Sean Spicer delivers a statement while television screen show a picture of U.S. President Donald Trump’s inauguration at the press briefing room of the White House in Washington U.S., January 21, 2017. (Carlos Barria/Reuters)

The scene: The White House press briefing room, a couple of weeks or months from now.

Sean Spicer, press secretary to President Donald Trump, white-knuckles the podium before a herd of reporters. No, no, he insists, the President certainly did not suggest the sky is green. He believes strongly in a blue sky, and he was merely commenting on the fact that in certain weather conditions, the sky may appear slightly greenish. Next question?

Over in the Oval Office—or maybe from the gaudy spike of Trump Tower in Manhattan or the Mar-a-Lago receptionist’s desk—President Trump is watching CNN at a thunderous volume as he thumbs through Twitter. He narrows his eyes and purses his lips sullenly, then begins typing. Half a minute later, in the press briefing room, another hand shoots up. The President has just tweeted, “The sky is GREEN. Everyone knows that, only haters and losers deny it! Spicer doesn’t know what he’s talking about. SAD!” Would Spicer care to respond, and how does he square that with his prior remarks on the President’s true position?

It’s a preposterous but not remotely implausible scenario, given the administration that has just taken over the West Wing. In many ways, communication is the essence of Trump, his primary obsession and what won him the White House. He captivated voters with a gut-level appeal, becoming the embodiment of everything they were howling was wrong with their world.

He is fixated on his own coverage, apparently believing that any attention is good attention while simultaneously being offended by anyone who says mean things. And this is a man who, when he was bummed out by the weight of the transition following the election, launched a series of “thank you rallies” so he could go back to his happy place: roaring at crowds who roar right back.

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But for a man so infatuated with projecting himself and his message, Trump’s political communications operation looks from the outside like a baffling, undermining, unsophisticated, lunatic rodeo that leaves high-level political communications experts agog.

“It’s insanity times insanity to the square root of insanity,” says Andrew MacDougall, former director of communications to Stephen Harper.

“Who wants to work as a henchman for the Joker? Because you know when the bank job is over, he shoots all of you,” says Scott Reid, former director of communications to Paul Martin.

“It’s absolutely ridiculous,” says Patrick Gossage, former press secretary to Pierre Trudeau. “He’s broken all the rules.” Gossage adds that he spent years working for a guy who thumbed his nose—and flipped the bird—at the press, and he’s still gobsmacked by the Trump operation.

Kellyanne Conway, advisor to U.S. President-elect Donald Trump, departs for a church service before the 58th Presidential Inauguration in Washington, U.S., January 20, 2017. (Joshua Roberts/Reuters)
Kellyanne Conway, advisor to U.S. President-elect Donald Trump, departs for a church service before the 58th Presidential Inauguration in Washington, U.S., January 20, 2017. (Joshua Roberts/Reuters)

Peering across the border with an expert gaze, however, at least a couple of Canadian political operatives think Trump is only crazy like a fox, and doesn’t get enough credit for milking this new media landscape better than anyone else.

There are two things all of them are unanimous on, however. One is that the credibility of communications staff rests entirely on the belief that they speak with authority on behalf of their boss. The moment that’s in doubt—or, say, a Twitter missile from the Oval Office blows a hole clean through it—spokespeople end up looking like a defenceman who’s dropped his stick in front of the net: they’re still scuttling around trying to do their jobs, but they’re functionally useless.

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Here’s the second thing they agree on: every one of the Canadian political advisers who spoke to Maclean’s laughed for an uncomfortably long time when discussing Spicer’s admission that he has no prior knowledge of his boss’s tweets, meaning that each morning he gets to find out which brown bags were ignited and left on porches overnight. “I can’t imagine waking up and not knowing what your boss is going to say, how you could possibly do your job,” says Amanda Galbraith, former communications director to Toronto Mayor John Tory.

In a more conventional political operation, spokespeople know their boss’s positions, approach and language quirks well enough to speak for them. There’s more back-and-forth when the working relationship is new, but eventually, they spend enough time together to channel their politician by osmosis. “Imagine basically handing your voice over to someone for eight hours a day on really important issues,” says Galbraith, who spent 16 hours a day in a car with Tory for months during the campaign before they landed in the mayor’s office.

Political communication is normally “such a deliberative, careful act,” MacDougall says: nothing comes out of your mouth that hasn’t been passed through a fine sieve of advisers and polished within an inch of its life. There’s a reason bad things happen in crisis mode, when you’re making it all up as you go along, he says.

In Trump’s camp, however, there’s little sense of trust; instead there are frequent public contradictions handled with offhanded aggression by Trump. A Washington Post story in October suggested that Kellyanne Conway, his campaign manager and now “counsellor,” attempted to corral her candidate by speaking to him through her appearances on the cable news programs he watched relentlessly. “He thinks he’s the show and they’re the little people that might help to smooth some of it out, at least until he comes to contradict them again,” MacDougall says.

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Responding nimbly to the unexpected is the fabric of politics, says Galbraith—but you never want the surprises lobbed at you from inside your camp, as often seems to be the case with Trump & Co. With her clients, Galbraith has a full-disclosure policy: I’ll give you my best advice, but if you go rogue, I can’t predict what’s going to happen. It’s like the lawyer-client relationship: it only works if everyone lays their cards on the table. “You can’t protect them from what you don’t know about,” she says.

Political communication is a bit of an ongoing advertising campaign: you have a core message to get out, so you coordinate all the bits of your orchestra—your cabinet, party members, policy announcements, surrogates—to play the same melody. Except if you work for Trump, and then whatever message you planned to advance gets blown out of the water by the intemperate remark, conflict or controversy du jour.

Gossage sees one simple—if apparently impossible—fix for this. “Getting a consistent message from Trump wouldn’t be that hard if he wouldn’t tweet!” he says, laughing, which is something you can do when it isn’t your job to deal with it.

However, Galbraith thinks some of this seeming disarray is more staged and strategic than it looks. For one thing, it projects the identity that got Trump to the White House in the first place. “Authenticity is key to his brand—part of that is he can’t be controlled,” she says. “He was elected to be sent down to Washington to knock sense back into the elites, not become part of the system.”

And sometimes amid the apparent chaos, she believes Trump and his team are in fact playing a game of, “Hey, look at the shiny, weird thing over here while we quietly do something more substantial in the wings.” “Sometimes it may be deliberate in that they want something in the window to distract from something else, and people follow those easy stories,” she says.

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Bill Fox, former communications director to Brian Mulroney, argues Trump and his team have understood the current media environment better than their opponents all along, grasping that authenticity trumps the authority of the old-guard gatekeepers. History is full of successful politicians who owned a new medium, he points out: Franklin Roosevelt’s genius for radio, John F. Kennedy shining on television, and, in Canada very recently, Prime Minister Justin Trudeau and his team leveraging social media better than any before them.

Fox believes it’s less a case that Trump is crassly oblivious to the normal rules of effective political communication and more that he rotated the game board 90 degrees and made it his own. “I think he understood some of our rules better than we gave him credit for,” he says. “He knew how to use them to his advantage.”

Reid, however, vehemently disagrees that there’s any method to the Trump communications madness. “He is exactly what he looks like: an impetuous, petulant child,” he says. “He can’t maintain that discipline because he’s unwilling to give ground. It means they’re going to take themselves off-message and be distracting constantly.” But, he adds, you get the pronounced feeling that they just don’t care: sometimes it’s like Conway and Vice-President Mike Pence are characters in The Office, turning to smirk and shrug at the camera: there goes Donald, Trumping again!

Reid says Trump’s spokespeople come in only two varieties: “lunatics and lapdogs.” Katrina Pierson is an example of the first category—a surrogate willing to spit out absurd lies on Trump’s behalf (for instance, that Barack Obama started the Afghanistan war, apparently with the aid of a time machine). And then there are lapdogs like Spicer, who operate with “a perverted sense of priority,” Reid says: rather than trying to advance their guy’s cause, they’re just trying to avoid getting publicly smacked with a newspaper.

Karl Belanger, former press secretary to Jack Layton and principal secretary to Thomas Mulcair, says that in some ways, what Trump and his team are doing is a throwback: muddying the waters to introduce advantageous doubt is an old political trick. There’s a tale about Lyndon Johnson seeding a rumour that his opponent was, uh, amorous toward pigs. When an aide protested in horror that it wasn’t true, Johnson supposedly replied, “I know. I just want to make him deny it.” What’s different here, Belanger says, is the extent to which Trump and his team play this game—and the fact that the boss happily dives into the muck himself rather than sending a Luca Brasi on his own behalf.

The other aspect of the incoming presidential communications shop that Belanger finds novel and mind-boggling is the sheer brazenness of it, as exemplified by the number of times they have flatly denied Trump said or did something for which there is obvious evidence.

The question now is how this model will function in the West Wing. Top political adviser jobs typically have a short lifespan because the stakes are so high, and the rate of burnout and heads rolling corresponds (Barack Obama went through three press secretaries over his eight years in office). “When you wear the director of communications or press secretary shirt, you’re basically the guy on Star Trek with the red jersey on—you know you’re gonna die at some point and you’re expendable,” MacDougall says. “The president’s the president.”

But this administration seems destined for a higher than average level of churn, because what makes the job of speaking for—and delicately around—Trump so central is exactly what will make it treacherous, too. Image and chatter is what Trump appears to care about above all else. It’s almost touchingly obvious how obsessively he watches his own coverage—even Saturday Night Live, that rotting, irrelevant NBC carcass that he just cannot resist clawing at week after week. So of all the pieces of the White House machinery whirring around him, it’s the words deployed for and about him that Trump will most keenly scrutinize and react to: they will be his litmus test for loyalty and audacity.

As Reid says, “I would think working as Donald Trump’s spokesperson would be the most dangerous job in Washington.”