January 11, 2024 03:00 PM

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Trump 2024

‘The Hardest Worker In All Of Trumpland’: Steven Cheung And The Professionalization Of Trump’s 2024 Campaign

Editor’s note: NOTUS is coming very soon, but before then, we’re sharing a few final pre-launch stories. Today, we’re profiling Trump campaign spokesperson Steven Cheung. He has emerged as a notably aggressive public voice in the 2024 election — but who is he behind the scenes?

Did you miss our story about the private meetings where Black women gave Team Biden an “earful”? Check it out here. And if you haven’t subscribed yet, please sign up for early access at NOTUS.org.

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By Cameron Joseph

As Republican Florida Gov. Ron DeSantis prepared to debate Democratic California Gov. Gavin Newsom on Fox News in late November, Steven Cheung — former President Donald Trump’s pugilistic communications director — decided to weigh in. “Ron DeSanctimonious is acting more like a thirsty, third-rate OnlyFans wannabe model than an actual presidential candidate,” Cheung said in a press release, predicting that DeSantis would “flail his arms and bobble his head wildly, looking more like a San Francisco crackhead than the governor of Florida.”

Even by the rough standards of contemporary American politics, the tone was combative. But for Cheung — who has risen to become one of the most powerful people in Trump’s orbit — it was hardly out of the ordinary. He has issued dozens of statements mocking DeSantis (“The only lift he’s received throughout the campaign is from his high-heeled shoes”) and he has no problem making it personal (“Baby girl, who hurt you?” he sniped at DeSantis spokesperson Christina Pushaw in one post on X, formerly known as a tweet).

His barbs are hardly confined to the DeSantis team. When Trump pledged to “root out” the “vermin” living in the United States, some academics compared the former president’s rhetoric to Hitler’s and Mussolini’s. Cheung’s response: “Those who try to make that ridiculous assertion are clearly snowflakes grasping for anything because they are suffering from Trump Derangement Syndrome and their entire existence” — he later clarified that he meant their “sad, miserable existence” — “will be crushed when President Trump returns to the White House.”

Cheung’s slashing approach to communications has helped define the tenor of the campaign. “He’s extraordinarily aggressive,” said Trump senior adviser Chris LaCivita. Cliff Sims, Cheung’s friend and former campaign and administration colleague, called him “an absolute savage” who “lives for the fight.”

It’s easy to see why Cheung is a natural spokesperson for Trump, who, as he runs for president again, seems more truculent and vengeful than ever. Cheung is also far from Trump’s first bomb-thrower. But what distinguishes him from some of Trump’s earlier aides is that, behind the scenes, he is something very different: a non-self-promoting, even-keeled and disciplined professional.

Former White House chief strategist Steve Bannon — a close Cheung ally since the 2016 campaign who has twice hired him as a consultant — said that Trump’s orbit has long included people who are “high on big personality, low on competence, and lower on hard work.” Cheung, said Bannon, is “the exact opposite. He’s supremely, supremely competent. He’s also probably the hardest worker in all of Trumpland.”

As Bryan Lanza, a friend from the 2016 Trump campaign, put it: “Cheung is the ultimate capo, right? Like if this was a mafia organization, he just does the job and does it quietly.”

Reporters who’ve worked with Cheung mostly have nice things to say about him, too — a rarity for Trump aides. I interviewed five who’ve known him for years, including some at outlets that Trump likes to publicly disparage. They variously described him as someone who, in the course of fiercely defending Trump, is “competent,” “very savvy” and helpful when he can be. And unlike some past Trump staffers, he’s not prone to tantrums or bullying. If he’s unhappy, he’ll let reporters know by freezing them out — not by screaming. “He never overtly gets really fucking furious,” said one reporter. “He’ll just stop talking to people.”

In past election cycles, and during his four years in power, Trump was clearly hamstrung by the rivalries, factions, leaks, back-stabbing and general disarray that surrounded him. Now, for the first time since he entered politics in 2015, he appears to have a team of senior advisers who combine an innate understanding and embrace of his aggression with a striking lack of internal drama. It’s still early, of course, and Trump is still Trump — prone to shooting his mouth off and listening to a wider universe of outside allies who can be counted on to cause chaos. But if recent polls are any reflection, the campaign itself is working strikingly well as primary season begins in earnest. And Steven Cheung — with his cutting public voice and his private competence and calm — is emblematic of this new era.

***

There’s no getting around it: Cheung is a large dude, which impacts how people see him. Campaign senior adviser Susie Wiles told me that Trump has jokingly referred to Cheung as “my sumo wrestler.” “Look at those hands. You’re in good shape if he’s with you,” Trump has commented about Cheung in his presence, according to Wiles (a funny fixation for a politician self-conscious about his own hand size). “Nothing bad’s gonna happen to you.”

“He is a very intimidating, imposing individual, just because [of] the sheer size and look. He has a very menacing look,” said one GOP strategist who worked with Cheung during his time in the White House. “He’s actually a really nice guy — if you are on the same team, and you’re focused on the same mission.”

Cheung, a former hobbyist muay Thai boxer and taekwondo fighter, knows how to use his physical presence. As reporters entered the post-debate spin room after the first GOP debate in Milwaukee last August, Cheung positioned himself to make sure they couldn’t leave Trump out of the story just because he’d skipped the debate.

“He was standing almost in the entrance of the spin room — and he’s a big guy — taking up space physically as an enforcer for Trump and just dunking on like every other candidate, making fun of every other candidate,” Semafor reporter Dave Weigel told me.

“He’s in the kind of insult comic line of spokesman,” Weigel said. “If you email him, you expect something very salty, very quickly. He’s good at that.”

Trump knew who Cheung was during his White House years, but Cheung was never among the many aides trying to worm their way into an Oval Office meeting with the president or clamoring for appearances on cable TV or a trip on Air Force One. Today, said Wiles, Cheung is by Trump’s side “a lot.” “The President will often say, ‘Let’s let Steven decide’ how to handle matter ‘X,’” she explained, noting that Cheung’s opinion often carries the day during group discussions on strategy.

“He is now clearly in the inner circle,” said Sean Spicer, the former White House press secretary. “And the thing is, he’s earned it. He’s worked his way up, as opposed to some people who tried to crash into the inner circle.”

Cheung’s path to the top ranks of American politics began in his hometown of Sacramento, California. His immigrant parents — his father is from China, and his mother is Chinese but grew up in Japan — met during college while studying in Sacramento on student visas. His first political experience was volunteering on Arnold Schwarzenegger’s successful gubernatorial campaign in 2003 while in college at California State University, Sacramento; he then interned and worked in the Schwarzenegger administration before landing a low-level job on then-Arizona Senator John McCain’s 2008 presidential campaign. Someone on the campaign nicknamed him “Panda” (“Kung Fu Panda” came out that year), and Cheung embraced the moniker: His X (formerly Twitter) handle, until recently, was @californiapanda.

Cheung subsequently worked for two Tea Party-fueled campaigns: Steve Poizner’s run for California governor, followed by Sharron Angle’s campaign against then-Democratic Senate Majority Leader Harry Reid in Nevada. Angle’s campaign was a mess — the anti-immigration candidate at one point told a group of Latino high schoolers that “some of you look a little more Asian to me” — and, by election day, it had turned into a circular firing squad, as the establishment pros openly feuded with Angle’s diehard activist backers over strategy. However, multiple colleagues said they never heard Cheung complain.

Political flacks often take on the public personas of their bosses; not everyone in Trumpworld was as bombastic or aggressive in their previous lives. But Cheung always had a pugnacious edge. In 2011 and 2012, while working on then-Texas Lt. Gov. David Dewhurst’s Senate campaign, Cheung’s job was to take the shine off Tea Party icon Ted Cruz — Dewhurst’s primary opponent — with daily attacks. “Red Ted shows his true colors, consistently stands with China against American interests,” read the subject line of one Cheung email. The nickname may seem quaint by today’s standards (when Cheung called DeSantis “Red Ron” during this campaign, no one even noticed) but it caused Cruz’s allies to go ballistic — and by all accounts, hurt Dewhurst. “All that stuff just backfired,” said Brendan Steinhauser, a Texas GOP strategist who worked for the pro-Cruz group FreedomWorks in that election. “Primary voters just did not react well to that stuff.”

Dewhurst lost the primary, and Cheung was ready for a break from politics. Friends said he had mentioned a desire to work in sports communications for years. Soon, the Ultimate Fighting Championship came calling.

Working from Nevada, Cheung did plenty of normal sports communications for UFC. He also went to war with the Culinary Union — which was targeting UFC’s owners as part of a unionization pressure campaign aimed at their hotels. Cheung was tasked with setting up a messaging operation to counter-attack the union and defend the UFC, which was fighting hard to get mixed martial arts legalized in New York state (where the Culinary Union’s parent union had a lot of pull). “That was a really important project for the UFC,” UFC Chief Operating Officer Lawrence Epstein told me. “Steven was a big part of it and created a huge amount of value for our company when we ultimately got the sport legalized.”

UFC was in some ways a dry run for Cheung’s current gig. The organization’s brash, brawny president, Dana White, has been friends with Trump for two decades, and they have similar personality traits. Both respond to controversy by doubling down, and both tend to act as their own spokespeople. “When you’re in communications, and you have a Dana White-type person, I think he would have learned a lot from that,” said Marc Ratner, UFC vice president of regulatory affairs. “And that may have helped him there with the president.”

***

By 2016, Cheung was itching to get back into politics. He tried old contacts who were working on the presidential runs of former Florida Gov. Jeb Bush and Sen. Marco Rubio, without luck. When Trump secured the nomination — and had to staff up fast — Cheung reached out to Jason Miller, who had recently been hired by Trump’s campaign. Miller needed a war room director to respond to incoming criticism and push out a stream of attacks against Democratic opponent Hillary Clinton. “I remember seeing his email come through. My first reaction was ‘Oh, man,’” Miller recalled. “Nothing says ‘war room’ better than someone coming right from the UFC. How great is this?”

Cheung flew straight to Cleveland, where the Trump team was scrambling to prepare for the convention. There, he immediately dove into the chaos, helping an understaffed team as it warded off a last-ditch effort to block Trump from the nomination.

His fighting instincts were on display from the start. One night, Lanza, Cheung’s hotel roommate for the convention, returned to their room to find that Cheung had dozed off while watching news coverage of the convention. After searching for the remote to shut off the blaring TV, Lanza realized that Cheung must have rolled over on top of it, and went to extricate it. Suddenly, Cheung was awake. “His hand went straight to my throat,” Lanza recalled, with a laugh. “In his calmest [voice, he asked], ‘What are you doing in my bed?’”

After the convention, Cheung headed to New York, where he helped set up the campaign’s war room on the 14th floor of Trump Tower. Cheung was almost always the first in the office and the last to leave, regularly working 20-hour days and falling asleep at his desk — sometimes intentionally, sometimes by accident — for 15 to 20 minutes until his computer or phone started pinging at him. His colleagues started referring to the quick rests as “panda naps.”

Cheung spent a lot of time fighting for better media coverage. He’d often call reporters and editors seeking a change on an already-published story — not a wholesale rewrite but a small edit to a phrase or a headline. He obsessively watched the cable news networks and gained a reputation on the campaign for being able to get CNN or MSNBC to tweak a chyron.

When things went sideways, Cheung didn’t flinch. On the day when Trump’s infamous “Access Hollywood” tape dropped, some campaign staff made themselves scarce. Cheung helped set up the response video from Trump. “He was one of the few guys that didn’t panic,” Bannon said.

In an email, Kellyanne Conway, who served as Trump’s campaign manager from mid-August through the election, called Cheung “an MVP and an unsung hero” of the 2016 operation.

On election night, Cheung got to celebrate with some old colleagues. The UFC had finally won approval to host events in New York, and White and Epstein were in town ahead of the UFC’s first fight there — which Cheung’s work had helped make possible. As the shocking election returns rolled in, they headed over to the surprise victory party at the Midtown Hilton. White spotted Cheung and hugged him, congratulating him on the upset. “It all came together that night,” Epstein said.

***

Cheung helped with the presidential transition, then followed Trump to the White House. He didn’t land a prominent on-camera role or a West Wing office, but he was made assistant communications director and, later, White House rapid response director.

It was a sprawling, poorly defined press operation with competing loyalties and old rivalries between ride-or-die Trump campaign staffers like Cheung and former Republican National Committee staffers — plus simmering tensions between different cliques from Trump’s campaign, which had cycled through three campaign managers. There’s a reason Cheung’s friend Sims titled his White House memoir “Team of Vipers.”

Cheung was part of the Bannon clique that often sparred with the more establishment types. But he managed to largely avoid the drama and was tasked with some significant work. He helped administration nominees prep for their Senate hearings and coordinated the White House’s public defense of various selections, including Ben Carson and Betsy DeVos.

Cheung’s portfolio included two of the biggest wins of the early Trump administration. He was the point man for the White House’s communications efforts on confirming Neil Gorsuch to the Supreme Court, and he also played a key role in Trump’s signature legislative achievement — a massive tax cut for both individuals and businesses.

“He’s not the kind of guy that you’re sitting around [with], yukking it up” during work hours, Spicer told me. “He is the kind of guy that puts his head to the ground and gets the job done. And you don’t want to be the lazy person … standing in his way.”

Stephanie Grisham, who worked with Cheung on the 2016 campaign and in the White House (and later broke with Trump over the Jan. 6 insurrection), said that he was “quite smart” and excelled at “pithy statements that can offend people quickly, which is exactly what Trumpworld likes.”

Cheung lasted in the administration until new White House Chief of Staff John Kelly cleaned house in June 2018, firing many Bannon-aligned staffers as he sought to take control of an operation known for leaks. He was one of the final Trump campaign staffers to hold on in the White House.

Cheung set up a comms shop, consulting for some corporate clients and working for Bannon. He didn’t take a full-time job on the 2020 campaign but came in as a senior communications adviser over the summer as part of a campaign shake-up. Staffers said Cheung helped stabilize a campaign that had been flailing since COVID-19 hit.

His main job was to pull together a chaotic Republican National Convention that Trump had belatedly, reluctantly agreed to scale down because of the raging pandemic. He took charge of producing convention videos — including one featuring Mark and Patricia McCloskey, who’d stood on their St. Louis lawn and waved guns at Black Lives Matter protestors earlier that summer. Later, he helped Trump with debate prep.

Cheung’s role with the campaign officially ended after Election Day. It doesn’t appear that he was involved much in Trump’s post-election coup efforts. He took vacation trips to Las Vegas and Hawaii. His name never comes up in the House Jan. 6 committee’s report.

Cheung has deleted his old X (formerly Twitter) handle @californiapanda, switching to a more professional-sounding @thestevencheung, and while the internet archive has his old posts, there’s a gap between mid-November 2020 and late January 2021 — so it’s unclear how, exactly, he felt about the insurrection in real-time.

What we do know is that a week after the election, he retweeted a fuzzy-math conspiracy-theory video from then-Trump adviser Steve Cortes arguing the “statistical case” that suggested voter fraud in the election. And one of Cheung’s final tweets before the gap is from Nov. 11, days after the networks had called the race for Joe Biden. He trollingly quote-tweets a story about Biden officials fretting that a MAGA crowd would turn out for his inauguration. “Wait... I remember a time when Biden claimed he’d represent all Americans,” he tweeted. “I guess it’s moot because there won’t be a Biden inauguration.”

***

Cheung advised Trump frenemy Caitlyn Jenner on her quixotic California gubernatorial run in 2021 and seriously considered running for Congress himself in 2022, talking to GOP officials and donors about whether he could flip a California seat being vacated by a retiring Democrat.

But Cheung opted against a campaign, instead returning to work for Bannon for a few months, then taking on a pair of Bannon-backed MAGA candidates — former Republican Missouri Gov. Eric Greitens, who sought a comeback in a Senate race after resigning in disgrace amid allegations of blackmail and sexual misconduct, and former Rep. Jim Renacci, who challenged GOP Ohio Gov. Mike DeWine. Both failed to secure Trump’s endorsement and lost their primaries.

Through it all, Cheung stayed devoted to his old boss — even as many Trump-endorsed candidates went down in flames in the midterms and Trump himself looked listless, undisciplined and vulnerable to a 2024 GOP primary challenge.

Some who know Cheung think he can be loyal to a fault. “He’s going to be one of the last few guys in the bunker with Trump at the end of the day ... barring the door with a suicide vest,” one Republican who worked with Cheung during his time at the White House told me.

But that loyalty has paid dividends. Right after Trump launched his campaign in November 2022, Wiles made Cheung one of her first senior hires. He now manages more than a dozen staffers overseeing rapid response, communications, research and surrogate management.

His go-to approach is to double down on what the president is pushing rather than trying to steer him in a new direction. “The secret to longevity in Trumpworld is to remember whose name is on the door. And that’s where someone like Steven, who very much keeps that in mind, has been able to remain such an important player for such a long period of time,” Miller said. “I think that President Trump recognizes that and appreciates his loyalty and his work ethic.”

As the official voice of the campaign, Cheung has set a tone that often sounds less like traditional politics and more like the worlds of wrestling or mixed martial arts. That isn’t a coincidence. “Like me, Cheung isn’t just your typical casual fan of pro wrestling — he is a full-on nerd about it,” Andy Surabian, a White House veteran who is now Donald Trump Jr.’s spokesperson, said in a text. “We’ve gone to numerous wrestling shows together, and I think both of us see the similarities between the world of pro wrestling and the world of politics.”

Surabian’s boss offered his own enthusiastic endorsement. “Cheung is just an absolute beast,” Trump Jr. told me in a statement. “He’s a good friend and has always been loyal to my family and our movement. He’s the perfect fit for my father: Talented, hard working and has a gigantic set of balls!”

Cheung has traveled with Trump to almost every one of his court appearances in the past year and has played a key role in developing a communications strategy that simply lumps all of Trump’s myriad legal woes into one amorphous, politically motivated attack by his foes.

“This is nothing more than election interference,” Cheung declared to the cameras on the courtroom steps in early October ahead of Trump’s appearance in his New York civil fraud trial. “The Biden-led witch hunts against President Trump and the American people will fail,” he said in a December statement following a U.S. Court of Appeals for the District of Columbia Circuit ruling that Trump’s gag order would mostly stay in place.

Cheung has led the efforts to get Trump on more non-traditional media. That included an interview on Full Send, a bro-y, MAGA-friendly podcast hosted by the Nelk Boys, a trio of Canadian pranksters. (It was later taken down by YouTube for disinformation because Trump repeated his 2020 falsehoods.) There have also been discussions about Trump appearing on podcasts from Barstool Sports and Mike Tyson.

Trump has had plenty of appearances with Cheung’s old colleagues, too. The former president has attended multiple UFC events, walking out with White, Tucker Carlson and Kid Rock at an early November fight in New York. UFC fighters have spoken at Trump rallies, and Trump sat down with former UFC fighter Matt Serra and comedian Jim Norton for a 40-minute interview on their “UFC Unfiltered” show in July. Multiple sources said that this comes mostly from Trump’s two-decade friendship with White. But Cheung was with Trump for all of these appearances.

He has also led the attack on Trump’s GOP rivals. For months, Cheung has sent out a daily “Kiss of Death” email attacking DeSantis. Some recent subject lines include “Ron the Moron,” “Tiny D-Day,” “DeSantis Debate DeSaster” and “little league brain in a major league world.” When DeSantis’ campaign responded with a “Trump accident tracker” in late October, Cheung called it a “weak, bitch move by a dying campaign.”

“They were arrogant and cocky — and it’s Steven Cheung that took them down,” Bannon said of the DeSantis campaign.

Cheung seems to take particular delight in trolling Pushaw, the DeSantis spokesperson. After Cheung mocked the “amateur” staff work for what he called a “horrible, shitty candidate” at one September DeSantis campaign event, Pushaw fired back by mocking Trump for being insufficiently tough on trans rights: “Can a man become a woman?” she wrote. Cheung replied, “You asking for yourself?”

He’s been just as aggressive toward any and all Trump foes, calling Cassidy Hutchinson, a former administration official and later Jan. 6 whistleblower, “a liar and fraud.” He derided other former Trump aides — among them Grisham, who wrote a tell-all book — as “media whores” and “charlatans” “always looking for their next grift … because they know their entire worth as human beings revolve around talking about President Trump.” He’s not much easier on Nikki Haley, referring to her by Trump’s favorite nickname, “Birdbrain,” in various campaign missives. As she has risen in the polls, he’s pivoted to attacking her in his “Kiss of Death” emails, labeling her “Nikki New Taxes” and “Open Border Nikki.” Weighing into a recent spat between DeSantis and Haley staffers, he wrote, “When two loser comms staffers on losing campaigns shout at each other, and there’s no one around to hear them, do they actually make a sound?”

It hasn’t all been smooth. During a September campaign stop at a gun shop in South Carolina, Trump spotted a Glock that featured a picture of him, and said, “I want to buy that.” Cheung incorrectly posted on X that Trump had bought the gun — which would have been illegal because he’s currently under criminal indictment.

Yet even on bad days, Cheung has maintained his cool. One reporter told me that Cheung helped arrange an interview with Trump for an article that didn’t paint a flattering portrait. Trump was furious at the resulting story — but Cheung didn’t blame or freeze out the reporter. “He had a sense of humor about it and didn’t take it personally,” the journalist said, while adding that “he did seem to tread more carefully in the months that followed.”

A lot of factors, of course, have conspired to put Trump in a much stronger political position heading into 2024 than he was a year ago — especially his myriad legal troubles, which have rallied the GOP base behind him. Still, there’s no doubt that Trump’s staff has so far largely avoided the kind of unforced errors that plagued his past campaigns. Their efforts have helped set Trump up well to weather the inevitable ups and downs of a long election season, and Cheung has been a major part of that early success story.

“Every faction in Trumpworld loves the guy — and depends on him, quite frankly,” Bannon told me. “He’s the key to the nerve center.”

“He is incredibly competent, no drama,” said Wiles. “Those are two things really important to any presidential campaign — particularly this one. And he has both in abundance.”

Lately, as Trump has begun to look past the primary to the general election, Cheung has ramped up his attacks on President Biden. In a recent statement to The Messenger, Cheung said that Biden was “in a constant state of confusion, shuffling around like a Roomba, and falling on his ass in front of the American people because he’s weak and frail.” Biden, Miller told me, “is very much going to regret the day that Steven Cheung turns all of his attention on him.”

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Cameron Joseph is a freelance political reporter with recent work in The Guardian, the Los Angeles Times, Rolling Stone, and Politico Magazine. A recipient of the 2023 National Press Foundation Dirksen Award for distinguished reporting of Congress and the 2020 National Press Club award for excellence in political journalism, he previously worked for VICE News, Talking Points Memo, The New York Daily News, The Hill and National Journal.

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