[W]ESTON — Assigned to cover President Donald Trump, Vanity Fair correspondent Gabriel Sherman seemingly doesn’t stop working. So the Middlebury College graduate was only half-joking when he arrived for a Saturday-night talk at Weston Playhouse’s Walker Farm theater and asked the audience a question.
“While I was waiting backstage, no one was indicted, right?”
Sherman had just filed a story, “Trump Believes There’s A Coup,” that noted “yet another deluge of horrible news” in a month that has seen a new Bob Woodward book, an anonymous New York Times op-ed and, on Friday, a surprise guilty plea from the president’s former campaign chairman Paul Manafort.
“The West Wing is bracing for the climate to worsen,” Sherman writes in his latest piece. But as someone who has tracked the current president for nearly two decades, the journalist has plenty of practice braving the elements.
“I’ve been covering Donald Trump since the start of my journalism career,” said the 39-year-old whose family has visited Weston since he was a teenager. “He’s been using and abusing the press for a long time.”
Sherman began reporting at the New York Observer, where he wrote a weekly real estate column.
“My editor said, ‘If you need a quote, call Donald Trump.’”
Sherman has, often. Moving on to New York magazine, he covered the billionaire’s 2016 presidential bid after writing the 2014 best seller “The Loudest Voice in the Room: The Inside Story of How Roger Ailes and Fox News Remade American Politics.”
“Trump engages with the press very differently than anyone at his level,” the journalist said. “He loves to gossip, cajole and bully. Ask a question and he just talks through you, he just filibusters. When he said Mexicans were rapists and ‘we’re going to build a wall,’ the national press said he was finished. I was one of the few who took him seriously and understood the message he was selling was resonating.”
Sherman recalls covering the candidate’s election-night event.
“As it progressed, you could almost feel the space-time continuum shifting,” he said.
The journalist’s job hasn’t been the same since.
“Every day it’s a firehose. The West Wing is what you see in the news — it’s worse behind-the-scenes. I can call up a half-dozen people and they will recount some episode.”
Then again, with everyone trying to determine who penned the anonymous New York Times op-ed, sources are scared of being discovered, sending many to encrypted-messaging apps.
Sherman, for his part, recently traveled with the president to Duluth, Minnesota.
“Trump is most comfortable when he’s speaking to the 30 percent of America that are his devoted followers. Where he lives is in the mutual admiration society.”
The president, in turn, has deemed the press the “enemy of the people.”
“I’m sort of used to it, but to tell people, as Trump does, don’t believe what you read or see, I think that crosses over a pretty significant line. I don’t know how you put the genie back in the bottle.”
That said, Sherman is seeing cracks in the president’s popularity.
“There are signs Trump has eroded his support, especially among Republican women. The picture of Trump being an unstable and erratic leader has been pretty well-defined. He’s going to test the limits of how one can govern with just-the-base strategy.”
Sherman will continue to juggle press assignments (he’s also a MSNBC contributor) while penning a screenplay (working title “The Apprentice”) about Trump’s rise to power.
“If there’s one silver lining of this moment, it has motivated myself and my peers to do some pretty amazing work,” the journalist concluded.
“There is such a vital need for real vigorous accurate reporting. There is a sense within our profession that people are contributing to the civic fabric of our democracy. You feel you’re going into trench warfare every day, but you know it’s for the right reasons.”
