(Update: One June 26, 2023, Fox News announced that “Jesse Watters Primetime” will debut on July 17 in the 8pm primetime slot. Tucker Carlson’s show Tucker Carlson Tonight was taken off the air in April. This story first appeared on June 16.) 

Jesse Watters seemed to be enjoying himself.

Dressed to impress in a black tux, the Fox News host puffed on a cigarette as he chatted with a small circle of Fox News colleagues. Following the 2016 White House Correspondents’ Dinner, ideological foes now stood elbow to elbow, drinks in hand, at MSNBC’s swank after-party.

At the time, Watters was best known for pulling off elaborately planned ambush interviews on “The O’Reilly Factor,” then Fox News’ top-rated show. 

Standing nearby was Ryan Grim, then the DC bureau chief for Huffington Post, and Grim’s friend and colleague, the liberal blogger Amanda Terkel. 

Five years earlier, Terkel had landed in O’Reilly’s crosshairs after she criticized a victims’-rights organization for having O’Reilly speak at a fundraiser. Watters had followed her from her home in Washington, DC, to a small beach town in Virginia where she was vacationing. There, on camera, he’d accosted her with angry questions about “why I was causing ‘pain and suffering’ to rape victims and their families,” Terkel would later recall.

Grim thought the incident with Terkel crossed a line. When someone mentioned Watters’ presence at the party, Grim saw an opportunity to flip the script and get Watters to apologize to Terkel on camera. 

“I thought he was an obnoxious frat boy who just went around bullying people,” Grim would later explain to Insider. “So I wanted to give him a dose of his own medicine.”

Grim turned on his phone camera and zeroed in on Watters. 

For a few minutes, Watters played along. “Oh yeah, she loves me!” Watters said. “Bring her over, bring her over.” (Terkel, it was clear, had no interest in Grim’s shenanigans and had shrunk back into the crowd.) 

“You went all the way out to, like, the middle of fucking nowhere,” Grim shot back, leading Watters in Terkel’s direction. “You can go five feet over there. Come on.” 

The rest of the exchange is by now as infamous as it is embarrassing. Still smiling but clearly getting fed up, Watters swatted the phone out of Grim’s hand. When Grim picked his phone up and trained it again on Watters, the smile was gone from Watters’ face. After some bluster from both parties, things got physical. 

No one came out of it looking great. 

The next day, the Drudge Report wrote it up as a “brawl.” The Washington Post called it a “nerdy fight” and allowed Grim one last dig: “Ambush guy can’t take getting ambushed.” 

At Fox, there was less concern about the fight itself than the fact that Watters had attended an MSNBC party at all. 

“Hey Champ, don’t go into the other team’s locker room after the game and spike the football,” Fox CEO Roger Ailes told Watters, according to Watters’ 2021 memoir, “How I Saved the World.”

But the most revealing thing about that night was the explanation Watters gave for why he’d gone after Terkel in the first place. “I ambushed her ’cause O’Reilly told me to get her,” he’d said during the fracas.  

Jesse Watters likes picking fights. And he is fiercely loyal to Fox News, his professional home of two decades, starting when he was 24. Though best known as O’Reilly’s attack dog until O’Reilly was pushed out of the network in 2017, Watters was also key to the launch of the right-wing Fox Nation blog. As cohost of “The Five” and on his own 7 p.m. show, Watters delivers the network’s talking points with a grin and a touch of levity. 

Now, as Fox prepares to relaunch its prime-time lineup following Tucker Carlson’s abrupt ouster in April, Watters seems to be on everyone’s shortlist to take on a bigger role at the network — and perhaps one of the network’s most coveted slots. 

“He’s able to laugh at himself, which takes the edge off a little bit,” said Erik Wemple, the longtime media critic for The Washington Post. “The message he got under O’Reilly was that here we have a reward system, a license for being a jackass, and he has ridden that idea the whole way along.”

‘A lack of a moral compass, honey’

Jesse Watters has much in common with Tucker Carlson, the man whose shoes he would no doubt love to fill. 

They both come from prominent media families. Watters’ great-grandfather published The Saturday Evening Post, and his maternal grandfather was the publisher of Better Homes & Gardens. Carlson’s father, a local TV reporter, would go on to manage Voice of America.

Both men attended exclusive private schools on the East Coast. Carlson, who’s nine years older than Watters’ 44, went to St. George’s, a prep school in Middletown, Rhode Island. Watters attended exclusive Quaker schools in suburban Philadelphia and Long Island. 

Both went to college at Trinity, a liberal-arts school outside Hartford, Connecticut. 

From there, their trajectories part ways. 

Carlson’s family fractured when he was young. His mother left when he was 6 to pursue a more bohemian life as an artist, befriending the likes of David Hockney, and later cut her sons out of her will. But Carlson remained close with his father and even helped out on his unsuccessful bid to become the Republican mayor of San Diego. 

Watters’ upbringing verged on crunchy, with mandatory summer stints in outdoor-leadership programs, he writes in his memoir. He describes his political “awakening,” while at Trinity, rather literally: Waking up from a nap, Watters found the TV tuned to C-Span and something suddenly clicked.

“I was listening to the Senate floor speeches and realized the Republicans believed in the same things the Founding Fathers fought for: limited government and individual freedom,” he writes.

From there, he became a devoted listener of Rush Limbaugh and Ann Coulter, the dominant right-wing shock jocks of the day, and discovered a love of provocation that would later become his bread and butter: triggering the libs. 

At first, this meant triggering his own family — introducing them to Limbaugh’s show during breaks from Trinity.

“My dad could handle it, but it gave my mom road rage,” Watters writes in his memoir. “She swerved into oncoming traffic once during a monologue about welfare reform. Limbaugh literally drives liberals crazy.”

Watters has found a far larger pool of libs to trigger since then, but he continues to delight in the consternation his politics provoke in his mom. He’s known to occasionally read aloud the texts sent by his mom on “The Five.” 

“You end up presenting a lack of a moral compass honey,” Watters quoted her saying in response to a 2018 segment on the Mueller investigation. “We all know you are a Trumpet — you need not scream it.”

Watters and Carlson also took very different routes in their respective quests for right-wing stardom.

Carlson got his start writing political profiles for glossy magazines and then brought his bow-tied, preppy conservatism to CNN as the cohost of “Crossfire” in 2001. Three years later, “Crossfire” got canceled after a notorious appearance by “The Daily Show” host Jon Stewart, who used the invitation to lambast the show for fueling partisan rancor and “hurting America.” 

After a period of mid-career doldrums that included the cancellation of another show, this time on MSNBC, for low ratings, and an appearance on “Dancing With the Stars,” Carlson arrived at Fox News in 2009. For the next eight years, he gradually built a name for himself at the network, until 2017, when O’Reilly’s dismissal gave him the chance to take the prime-time throne.

Watters, on the other hand, has been a company man at Fox since the age of 24. 

And while Tucker seized Fox’s top bully pulpit to push the bounds of acceptable political discourse far to the right, popularizing the so-called “Great Replacement Theory” that was once relegated to the extreme backwaters of white-nationalist thought, it’s not clear how invested Watters is in bucking orthodox political boundaries.

“He’s a follower,” Wemple said. “It’s astonishing to me how little originality there is in the stuff that he says.”

Through a Fox spokesperson, Watters declined to comment for this story. The network also declined to comment about its coming programming decisions. 

Andrew Lawrence, who monitors Fox News as the deputy director of rapid response for the liberal watchdog Media Matters, agreed with Wemple’s assessment of Watters. Carlson, by contrast, used the power of his plum prime-time slot to act as an “assignment editor” for right-wing discourse, aggressively pushing the envelope, while Watters has been content to follow the lead, Lawrence said.

“I don’t think he really understands how to use that type of influence in the way that O’Reilly and Tucker did,” Lawrence said. “He’s just some guy who’s been groomed to be a cable-news host, he has no expertise on anything. He just says the right words.”

A ‘heat-seeking missile’

Back in 2002, Watters spent his first days at Fox in a dungeon-like basement room labeling cassette tapes of news segments for $12 an hour, with no benefits, he writes in his memoir. 

When an opening for a production assistant came at “The O’Reilly Factor,” which at the time was sometimes pulling in as many as 6 million viewers in a night, Watters leapt at the opportunity and got it.

Watters’ first on-air opportunity came in 2003. An Alabama judge had recently sentenced a child sex offender to just 60 days in jail, and O’Reilly dispatched Watters to confront him on camera. As the judge tried to read from a prepared statement, Watters let loose with a rapid-fire stream of questions until the judge, shaken, disappeared back into his office. 

“I felt rude but righteous,” Watters wrote. “It was an emotional octave that I cultivated professionally for years to come.”

O’Reilly loved it, and the telegenic young producer quickly began to serve as the show’s “heat-seeking missile,” as Watters would later put it. He honed his shock-and-awe tactics to catch a subject off guard and make them look as foolish, villainous, or incompetent as possible.  

“The best way to handle me is to go totally mute,” Watters writes in his memoir. “Don’t give me anything to work with. What you say can be used against you in the court of public opinion.”

Watters has always justified his ambushes as a tactic or last resort, an aggressive pursuit of the truth. 

But in reality, “The O’Reilly Factor” staff would sometimes make only a cursory effort to reach a subject for comment, according to Joe Muto, who joined “The Factor” in 2007 as a producer and worked alongside Watters on the show for five years.

“It makes for good television to have Jesse chasing someone down the street and the guy slams the door in his face,” Muto said.  

Muto, who would become infamous in 2012 when he was fired for leaking unaired Fox News footage to Gawker, was much more liberal than Watters but still speaks fondly of him. 

“Jesse was conservative, and he’d talk about that openly,” Muto said. “But he wasn’t as ideological as some other people. He was always focused on what was gonna make good television. He always knew it was a game.”

Watters stood out as a favorite among the other junior staff and was the only one who consistently made it on camera, Muto recalled. While most of the staff wore jeans and T-shirts, Watters nearly always showed up to work in a suit, and often earlier than anyone else.

“Jesse was always sort of first among equals,” said Muto. “It always struck me that he had his eye on the brass ring. He looked the part of a person who should be on air.”

By 2011, Watters had his own recurring segment called “Watters’ World.” Watters would head to Ivy League colleges, or to protests in left-leaning cities, or to festivals in progressive enclaves like Telluride to produce heavily edited videos that highlighted the goofy, outrageous, or dumb things people would say on camera. 

Sometimes, as with Terkel, he would face blowback. 

In 2016, he faced a storm of controversy for a segment shot in New York’s Chinatown that many critics called racist, prompting a rare apology from Watters. 

A rising star

Clowning on college kids and sticking cameras in the faces of people who irked O’Reilly made Jesse Watters famous. Less well known is the role Watters played in the birth of Fox Nation, a blog that helped signal and urge along the network’s rightward drift.

Launched in 2009 with Watters as managing editor, Fox Nation was a clearinghouse for interesting links that might not reach the level of a television segment but that could still get a rise out of the network’s fan base and generate ad revenue. It was nakedly partisan, playing on every cultural and political flash point it could to stoke — and capitalize on — the grievances of an increasingly embittered right.

As managing editor, Watters was in charge of the site’s tone and content. 

On a given day, the site would serve up rage-bait stories with headlines like “Obama Dishonors Medal of Honor Winners with Horrible Gaffe,” “Transgender Mayor Takes Heat for Skimpy Outfits,” and “Lefties Complain CIA Doctors Violated Al Qaeda’s ‘Medical Privacy.'”

“I remember watching in astonishment,” Wemple said. “That was all a precursor to what Fox News has become day in and day out now.”

Fox Nation was designed to expose the cravenness of liberals, with a heavy emphasis on culture-war issues — a tendency that has mutated over the years into even more extreme fare. 

In retrospect, Fox Nation was a “mask-off moment” for the network, which at the time still clung to its “Fair and Balanced” slogan, said Muto, the former O’Reilly producer.

“The guys who ran the website were old-school hard-news guys and tried to run the site traditionally, with at least a hint of neutrality,” Muto told Insider. “I think Fox Nation arose out of people’s frustration that the website wouldn’t go more like Breitbart.”

Watters’ own star also continued to rise. In 2015, his “Watters’ World” segment became its own monthly show. According to a source who interacted with Watters at Fox before and after he got his own show, the success could go to Watters’ head. He became, the source said bluntly, a “total douchebag.”

“Fox News is the créme de la créme of people who have some kind of complex, a need for popularity, but deep down inside, they’re not cool,” the source told Insider, speaking on condition of anonymity to avoid retaliation from Fox. “And so when he got his show, he started acting like he was really cool. Just really smug.”

Then everything changed. In July 2016, CEO Roger Ailes left the network in the wake of numerous sexual-harassment claims, including from stars like Gretchen Carlson and Megyn Kelly.

The revelations hit Fox News like an earthquake, and prompted an explosion of new accusations against prominent men at the network — and the aggressive efforts the network undertook to keep those accusations from the public. Among the men who came under the microscope was Watters’ mentor, Bill O’Reilly.

On April 1, 2017, The New York Times revealed that O’Reilly, Fox News, and its parent company had settled sexual-harassment claims brought by five women, totaling $13 million. Within weeks, O’Reilly was forced out of the network where he had reigned supreme for more than 20 years. (A sixth settlement came to light later, bringing the total to $45 million paid to O’Reilly’s accusers.)

Watters maneuvered well through this chaotic period. Back in January, “Watters’ World” had gone from monthly to weekly, airing on Saturday nights. That April, O’Reilly’s exit overshadowed more good news for Watters, who debuted just days later on Fox’s roundtable show, “The Five.”

Chopping it up with cohosts who over the years have included Kimberly Guilfoyle, fellow funnyman Greg Gutfeld, and token liberal Juan Williams, Watters mixed an increasingly strident conservatism with wit and a good-natured affect. 

“His job on ‘The Five’ was basically to attack Juan Williams, and he did it with gusto,” Wemple said, calling Watters the “cackling court jester.”

But that sense of humor has also gotten him in trouble: Just two days after his debut as a cohost on “The Five,” Watters abruptly went off the air for a few days after catching flak for a lewd comment he made about Ivanka Trump. 

In 2019, Watters briefly became tabloid fodder when it emerged that his wife, with whom he had twin daughters, had dumped him a year prior because of his reported affair with a Fox News producer, Emma DiGiovine. His personal life faded from the gossip pages after he settled down with DiGiovine, whom he married that year and with whom he now has two children.

Despite these bumps in the road, Watters has been a staple of Fox News programming. “Jesse Watters Primetime” debuted in in early 2022. 

Within a year, Watters was drawing upward of 3 million viewers a night, occasionally even beating Carlson’s ratings. As part of the Fox News prime-time slate, he has remained well ahead of his competitors at CNN and MSNBC but rarely captured the level of attention given to Sean Hannity at 8 p.m. and Carlson at 9. 

Since Carlson’s departure in April, various hosts have tried their hand at his slot. But thus far, none have managed to stem the exodus of viewers from the network. 

Happy warrior

On his nightly show, Watters serves up right-wing red meat to an increasingly polarized audience while softening the delivery. 

“He still is kind of that happy warrior, always going for the joke, always has a smile on his face — or a smirk if you’re being less charitable,” Muto said. “I think he learned that from O’Reilly, that you have to be judicious in your anger and always mix in a bit of levity.”

His shows are densely littered with culture-war signifiers: “illegals” are overrunning the country, the “Biden crime family” is a virtual mafia clan, Democrat-run cities like New York and Los Angeles are violent wastelands populated by drug-addled unhoused people (who chose to be on the streets, by the way), and drag queens are coming for your kids — if critical-race theory doesn’t get them first. 

In one painfully drawn-out bit, Watters and a guest joked at length at the idea of teenage boys unwittingly masturbating to a transgender model on the cover of the Sports Illustrated Swimsuit Issue.

In the balancing act between outright denial of the results of the 2020 presidential election and alienating Fox’s conservative base by accepting the results, Watters has proven flexible indeed. 

“Right now, there’s evidence out there,” he said on “The Five” on November 16, 2020, more than a week after Biden had been declared victorious. “You’ve seen the affidavits. You’ve seen the irregularities. And this will be administered in court, and we’ll find out what the result is.”

He took a more careful approach on his own show, “Watters’ World,” bringing on guests like Newt Gingrich to sow doubt as Watters nodded along in concern, rarely pushing back on baseless claims of fraud. 

And it paid off: Amid the media frenzy surrounding Fox’s $787.5 million settlement with Dominion Voting Systems, Watters managed to keep a low profile, though a tranche of leaked texts offered a glimpse into how he was maneuvering behind the scenes. In one exchange with Carlson obtained by The Daily Beast, Watters argued that hosts like Neil Cavuto and Chris Wallace, whom he deemed to be insufficiently pro-Trump, should be canned. 

“Need some fresh blood,” Watters wrote, according to The Daily Beast. “Should hire some trump people.” (Cavuto remains at the network. Wallace left Fox News in late 2021.)

It remains to be seen if Watters can live up to the role for which he has been gunning for so many years, and win back the millions of viewers who have abandoned Fox since Carlson’s exit. 

The source familiar with Watters’ position within Fox News during the 2010s cited Watters’ long years of service to the network as the key to understanding his rise to stardom.

“There’s a supertight network of people who are part of the ‘OG crew,'” the source told Insider. “There’s not many of them left.”

And that could be just what Fox News is looking for. Carlson’s show did a lot to build up Carlson’s personal brand, but his racist, xenophobic, and misogynistic rhetoric became toxic to many advertisers. 

Watters, whose entire career has been at Fox News, might be a safer bet, according to Muto, the former O’Reilly producer.

“He’s not a total ideologue, and he’s malleable enough that he can fill any role you want,” Muto said. “Goofy ambush guy? Yeah! Angry cohost on ‘The Five’? Yep! He learned from Bill that the No. 1 rule is to get viewers and keep your advertisers happy.”

(Additional reporting by Jack Newsham and Katherine Long.)

Correction: June 16, 2023 — An earlier version of this story erroneously described Watters appearing temporarily in the time slot vacated by Tucker Carlson. Watters is not among the hosts who have filled in for that time slot. The story also mistakenly asserted that Watters graduated a year late from Trinity College. He graduated in four years.