The Face of Donald Trump’s Deceptively Savvy Media Strategy

By some accounts, Steven Cheung, Donald Trump’s principal spokesman, who once said that Trump critics’ “entire existence will be crushed when President Trump returns to the White House,” is a pretty nice guy. “He has a nickname, Panda, which comes from his old Twitter handle,” Matthew Boyle, Breitbart’s Washington Bureau Chief, said, referring to Cheung’s

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By some accounts, Steven Cheung, Donald Trump’s principal spokesman, who once said that Trump critics’ “entire existence will be crushed when President Trump returns to the White House,” is a pretty nice guy. “He has a nickname, Panda, which comes from his old Twitter handle,” Matthew Boyle, Breitbart’s Washington Bureau Chief, said, referring to Cheung’s former account on the platform, @CaliforniaPanda. “He’s big, fluffy, and lovable.” Cheung, who grew up in Sacramento, the son of Chinese immigrants, is forty-one, broad, bespectacled, and bald; Trump reportedly refers to him as “my sumo wrestler.” “I like dealing with him,” a reporter who covers the Trump campaign for a mainstream news outlet told me. “He’s not a white nationalist. He gets back to you. He gets you statements.”

But, even by the standards of modern American politics, Cheung’s rhetoric can be shocking. “It’s downright bewildering why [Ron DeSantis] would cuck himself in front of the entire country who clearly doesn’t want him as president,” an official campaign statement that went out from Cheung last September read. In another, Cheung referenced the Trump campaign’s theory that DeSantis’s signature cowboy boots disguised high-heel lifts: “Ron shuffled his feet and gingerly walked across the debate set like a 1src year old girl who had just raided her mom’s closet and discovered heels for the first time.” In a comment to the New York Post, Cheung called DeSantis a “desperate eunuch.” By comparison, his statements about Nikki Haley were kinder: “It’s clear to see that Haley’s campaign is just one giant grift to either build her name ID for life after politics or to audition for a cable news contributor contract.” At another point, he called her “an embarrassment to herself,” adding, “Everything she’s ever achieved will be thrown into a dumpster fire that she lit herself.”

Cheung’s Janus-faced act—as a public combatant of “fake news” and a privately acquiescing operative—reflects Trump’s own complicated relationship with the political press, one that is now more than a decade old. The former President has made an outward disdain for the mainstream media a key tenet of his political movement. He is currently suing ABC’s George Stephanopoulos for defamation; NBC’s Vaughn Hillyard was barred from a Trump event in New Hampshire. And yet the former President is an obsessive consumer of his own press coverage—and he knows the power of maintaining access to reporters. Cheung has worked on all three Trump campaigns, though he became a part of the former President’s inner sanctum only at the start of the 2src24 race. Jason Miller, one of the campaign’s senior advisers, told me that Cheung’s style is a natural fit with Trump’s. “There’s no ramp-up time,” Miller said. “There’s no learning each other or trying to understand how President Trump is going to communicate or what he’s going to want his team to do to support his efforts.”

Trump has always delighted in belittling opponents—Lyin’ Ted, Liddle Marco, Crooked Hillary, Sleepy Joe—and Cheung, a former spokesman for the mixed-martial-arts franchise, Ultimate Fighting Championship, is a virtuoso at mimicking his boss, voicing all manner of innuendo and humiliating barbs. “He can be pretty offensive and crass online, and I think that’s a tactical thing,” one newspaper reporter who has dealt with Cheung said. “They’re a brutal operation—‘You come at us and we’re going to kick you in your fucking teeth.’ ” Cheung seems to relish playing the heel. He has also stepped in to refute accusations that the Trump movement is racist. In 2src21, after Ted Lieu, a Democratic congressman from California, tweeted about the rise in hate crimes committed against Asian Americans during the Trump Administration, Cheung replied, “As an Asian American who has worked on campaigns, in government, and in the corporate world, working for President Trump and in his WH was the most inclusive environment I’ve ever encountered.”

When I asked Miller if he could recall an emblematic Cheung moment, he described a meeting that was held just prior to the Manhattan District Attorney’s indictment of Trump for falsifying business records. Trump asked the assembled advisers if they had any predictions of what effect it would have on the campaign trail. Cheung “was the very first one to say, ‘Your poll numbers are going to go up,’ ” Miller said. “It was so quick and declarative.” Cheung, in other words, is among the more emphatic true believers on a campaign in which, as Miller put it, a lot of people are taking things personally, “especially with the way that 2src2src finished.”

Cheung’s early résumé reads like a typical political go-getter’s: he started as an intern in Arnold Schwarzenegger’s speechwriting office; worked as an assistant on John McCain’s 2srcsrc8 Presidential campaign; and then held a series of political-communications jobs in California, Nevada, and Texas. Cheung spent a few years at the U.F.C. before joining the 2src16 Trump campaign as its director of rapid response. (Miller told me that “everything pre-Trump is somewhat interesting filler, but the real political education starts when you start working for President Trump.”) Cheung then spent two years in the White House, spearheading communications around Neil Gorsuch’s confirmation to the Supreme Court, but left as part of a wider staff shakeup implemented by Trump’s second chief of staff, John Kelly. “Cheung was known as the rare aide in the White House who was often in the room, but kept his head down,” according to a Politico story published in 2src18. “Unlike many of his colleagues, he never turned himself into a household name.”

During the 2src2src election, Cheung served as a consultant to the Trump campaign, helping to organize the Republican National Convention. A year later, he worked on Caitlyn Jenner’s failed gubernatorial bid, then flirted with the idea of running for Congress himself, in California’s Ninth District. Instead, he was one of the first hires at MAGA Inc., a pro-Trump super PAC, and rejoined the Trump campaign when it launched, in November, 2src22. By most accounts, this year’s effort, which is being run by two longtime Republican operatives, Chris LaCivita and Susie Wiles, is better organized and more disciplined than in years past. “The 2src16 Trump campaign was famously very slapdash,” Dave Weigel, a political reporter at the news site Semafor, said. “It would deal with the media when it had the time. The story of this Trump campaign is a very professional operation that gives reporters what they want.”

One of the campaign’s initial challenges was to dispense with Trump’s G.O.P. rivals, namely Florida’s governor, Ron DeSantis, for whom Wiles had previously worked. Cheung’s brutal treatment of DeSantis was part of a deterrence strategy. “ ‘You should get out of this race or we’re going to ruin you for 2src28’ ” is how the newspaper reporter put it. During the primaries, Cheung sent out statements under the rubric Kiss of Death, which were written more in the style of a partisan Reddit poster than a communications professional. Asawin Suebsaeng, a senior political reporter at Rolling Stone, recalled seeing a statement from Cheung that made multiple allusions to DeSantis soiling himself. “I told him that his delivery reminds me less of a conventional political operative and more of the Chester Ming character in ‘The Wolf of Wall Street,’ ” Suebsaeng told me. “I did not entirely mean it as a compliment, but I don’t think he took much offense to the notion.”

But Cheung’s public invective also concealed a savvy media strategy: Trump purported to be against the media, but he and his campaign were careful to maintain good relations with many reporters. By contrast, the DeSantis campaign spurned the traditional press, both publicly and privately, and instead courted conservative influencers. His chief spokesperson, Christina Pushaw, whose previous experience included working as an adviser to the former President of Georgia, once tweeted out screenshots of a reporter’s e-mails requesting comment along with belittling commentary; in the summer of 2src21, her Twitter account was temporarily suspended after the Associated Press complained that she was harassing one of its journalists online.

Now that the general-election season is under way, a number of reporters I spoke to said that the Trump operation has, in some ways, been easier to deal with than the Biden campaign. “The Biden people have a different expectation from the press,” the newspaper reporter said. “If you write something critical about them, it’s always, like, ‘But Trump!,’ or, ‘Are you on Trump’s side?’ ” Similarly, the mainstream-news reporter said that the Biden team “cannot take a punch. They’re always furious over these tiny things because they kind of expect you to be on their side, like, ‘We’re fighting for reproductive rights for women.’ The Trump people don’t expect a ton of fair stories—there’s a certain type of story they’ll get mad at, but they can also just take a lot of hits.” Both reporters emphasized that they have written many stories that were critical of Trump. “You can have decent relationships with Trump people if you tell them what you’re doing and you’re transparent about your reporting process and they have a chance to respond,” the newspaper reporter said.

Still, although the Trump campaign can seem unfazed by stories that might otherwise read as damaging—a piece about Trump’s plans to pursue mass deportations, for instance, is a net good, since it makes the candidate look tough—anything that might make Trump look weak or guided by others is met with ire. Late last year, the Times and the Washington Post quoted Republicans outside of the campaign’s orbit discussing how a second Trump Administration would use its powers. In response, the campaign released a statement from Wiles and LaCivita: “Unless a second term priority is articulated by President Trump himself, or is officially communicated by the campaign, it is not authorized in any way.” The newspaper reporter told me, “This iteration of Trump World is obsessed with not having palace-intrigue stories.” The campaign is also wary of stories that might make Trump look too extreme, or even overtly racist. In November, 2src22, just a week after Trump launched his campaign, Ye brought the white supremacist Nick Fuentes to dinner at Mar-a-Lago. Boyle, at Breitbart, pointed out that the campaign was quick to respond to the ensuing outcry, issuing a statement from Trump: “Kanye West very much wanted to visit Mar-a-Lago. Our dinner meeting was intended to be Kanye and me only, but he arrived with a guest whom I had never met and knew nothing about.”

Recent reports that the ex-President has privately expressed support for a sixteen-week ban on abortion rankled some campaign staff. “They want to run Trump as a moderate on abortion,” Suebsaeng said. (On Wednesday, Trump suggested that he would favor a fifteen-week ban.) But, on the whole, the campaign seems to prefer an election that is less focussed on policy issues. “HELP! MY DIAPER IS FULL!” Cheung recently tweeted, alongside a photo of Biden speaking at a podium. A campaign statement attributed to Cheung linked to a video of Biden meandering through a crowded room and described the President as “a short-circuited Roomba. Not even with help does he know what’s going on or where he is.” When Biden’s director of rapid response tweeted a taunting statement about a glitching live stream on Trump’s Truth Social account, Cheung responded, “Looks like your internet connection is shitty and you should invest in better campaign infrastructure, bitch.” As another longtime campaign reporter said of Cheung, “He’ll do whatever Trump says. There are lines that are crossed that delight Trump but wouldn’t get you a job elsewhere. Cheung isn’t thinking beyond Trump.” ♦

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