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10/03/2017 08:15 pm ET Updated Oct 04, 2017

The Unstoppable Rise Of Jesse Watters, 'Golden Boy' Of Trump's Favorite Network

A year ago, the Bill O'Reilly protege released his breathtakingly racist "Chinatown" segment. He's only gotten bigger since then.
Fox anchor Jesse Watters hosts "Watters' World" on June 9, 2016 in New York City.
Getty Images
Fox anchor Jesse Watters hosts "Watters' World" on June 9, 2016 in New York City.

Qanta Shimizu just wanted to get inside Chase Bank to pull out the cash he needed to buy his fried chicken. But the white man in the gray suit wouldn’t let him pass.

Standing on a corner in New York City’s Chinatown, the man told Shimizu he just had a few quick questions he wanted to ask. The idea made Shimizu nervous. He had only moved to the U.S. three years before, and his English was still rough.

But the man in the suit wouldn’t take no for an answer. He asked Shimizu, who is Japanese, what Chinese people thought about Donald Trump, then the Republican nominee for president. He asked if Japanese people looked down on the Chinese.

Finally, he asked if Shimizu knew karate. Shimizu explained he had recently started taking karate classes in Columbus Circle. The man in the suit asked him to demonstrate a punch. Just wanting to escape, an uncomfortable Shimizu did as he was asked.

Shimizu tried to put the strange incident behind him. He got his fried chicken and went home to his wife and kids. A few days later, in early October 2016, one of his friends sent him a video called “Watters’ World: Chinatown Edition.”

When Shimizu pressed play, he watched as the man in the suit mocked elderly people who spoke little to no English. He watched as the man got a foot massage from an Asian woman and as he questioned two other women before the segment cut to a movie clip of two giggling Asian schoolgirls. And he watched as the man ridiculed him, too, asking him to hit his hand. “That’s nothing,” the man told Shimizu, before the video cut away again ― this time, to a scene from a slapstick martial arts movie.

For nearly four minutes, the video depicted people in Chinatown as a collection of non-English-speaking, nunchaku-wielding, politically ignorant foreigners.

Shimizu had never heard of Jesse Watters when they met on the street that day. Watters hadn’t introduced himself as part of Fox News’ “The O’Reilly Factor,” Shimizu said. He often doesn’t ― the network says it considers the “Fox News Channel” emblazoned on Watters’ microphone enough of an indicator.

But Shimizu knew of Bill O’Reilly, then the most powerful man in cable news. And he knew he was horrified by what Watters had done.

“Exaggerating that kind of feeling and notion [about the Asian-American community] is his business,” Shimizu said of Watters. “But I don’t think that’s not racism. That can be racism. So I can say he’s racist.”

Across the country, people shared Shimizu’s disgust. Watters’ “vile, racist behavior … has no place in our city,” New York City Mayor Bill de Blasio proclaimed. Ronny Chieng of “The Daily Show” called Watters an “ignorant sack of shit.” Paul Cheung, then president of the Asian American Journalists Association, condemned Watters’ exploitation of “tired, racist stereotypes.”

Daniel L. Squadron, then a New York State senator whose district included Chinatown, alleged that the segment played into the “stereotyping, mockery and ... thinly veiled disdain for immigrants” that had become “all too common” in the lead-up to the presidential election.

Two days after the segment ran, Watters released a statement about it, saying it was “meant to be taken as tongue-in-cheek” and that he “regret[ted] if anyone found offense.”

But in the year since the video’s release, it has become clear that the segment didn’t hurt Watters’ career. Watters, who turned 39 in July, has since gone from a bit player within the Fox News universe to one of its bigger stars. In January, the network announced that “Watters’ World” ― for years a segment on “The O’Reilly Factor” ― would become its own weekly Saturday night show. In February, young men excitedly crowded around Watters at the Conservative Political Action Conference, where he was a bona fide celebrity.

In April, Fox News announced in a press release that it had decided to end its two-decade partnership with O’Reilly ― a decision that came amid harassment allegations against the host that led to an advertiser boycott of his show. The news that the network was ending the most popular show on cable news led the day. But buried in the release lay another announcement: Fox News was giving O’Reilly’s protege, Watters, a full-time co-hosting gig on “The Five” as a result of the reshuffling.

Since then, Watters has used his new platform to say that a lot of people wish President Trump was a dictator” and that Russia’s meddling in U.S. elections “doesn’t affect anybody.” He has also compared Muslim immigrants to a wine “from a risky region” and suggested that food stamp recipients should build Trump’s proposed wall along the U.S.-Mexico border.

Watters didn’t get in trouble for any of that. (A Fox News spokesperson noted that he works on the network’s opinion side, not its news side.) But he has won an important new fan: the U.S. president. Watters is one of only 45 people Trump follows on Twitter, and the president has been caught watching Watters’ show on Air Force One. In March, Watters received the opportunity to interview Trump one-on-one.

It might seem odd that Watters’ Chinatown blunder almost immediately preceded his rise. But it’s not so surprising. The broadcaster who made a career out of trafficking in stereotypes has lived his life as the embodiment of one: The white man who gets off easy.

A photo of a young Jesse Watters from a Friends Academy yearbook.
Friends Academy
A photo of a young Jesse Watters from a Friends Academy yearbook.

Watters is the product of a Quaker education. Born in Philadelphia, he attended William Penn Charter School, the oldest Quaker school in the world. The school emphasizes Quaker values — empathy for others and an appreciation for people from diverse racial, socioeconomic and religious backgrounds. Watters’ father and mother, Stephen and Anne, clearly believed in the school’s mission: They served as director of the middle school and director of lower school admissions, respectively.

When Watters was in high school, the family moved to Long Island, New York, where his father got a job as headmaster at The Green Vale School, an exclusive private school that runs through eighth grade, and his mother got a job as director of admissions. The Watters family lived on campus, but Watters was too old for Green Vale, so his parents sent him to nearby Friends Academy, another prestigious Quaker school attended by many Green Vale graduates.

Watters’ sister, Aliza, shared her parents’ liberal values, and would go on to shine at Friends Academy, becoming a star pupil before graduating summa cum laude from Middlebury College and attending Oxford University as a Marshall scholar. 

Even before Watters’ first day at the school, there were signs he would follow a different path.

As part of the application process, Watters visited for something of a tryout, one of Watters’ former classmates recalled. “It was a school that a lot of people got rejected from,” said the classmate. “You kind of understood that if you were there for the day, you had to present yourself a certain way.”

But when class began on the day of his tryout, the gregarious Watters suddenly put his head down on his desk, the classmate said. It was a small class and a small room, and he was right in front of the teacher. But he didn’t appear to care, and it didn’t matter either. He got in.

“Obviously as the headmaster of Green Vale’s son, he was never going to be rejected,” said the classmate, who, like many people HuffPost talked to for this story, requested anonymity out of fear of retaliation from Watters and Fox News. (Watters, through a Fox News spokesperson, said he couldn’t recall the incident.)

Watters repeated his junior year during his first year at Friends Academy, which Fox News explained was because of his family’s move from Philadelphia to Long Island. Once there, he immediately made his presence felt. He liked to debate the best way to wear the collar of a polo shirt, his friend Michael Shlofmitz said over email. Others said he would joke about his “hippie” parents, and people described him as friendly and charismatic. He played football and lacrosse. Parents generally liked him.

“He was surprisingly popular,” a second former classmate said.

Even in yearbook photos, Jesse Watters stood out from the rest of the crowd. 
Friends Academy
Even in yearbook photos, Jesse Watters stood out from the rest of the crowd. 

But Watters was far from a star student, and he could occasionally display a shamelessness his peers found jarring. At one of his friend’s parties, Watters was told there was only one rule: Don’t go into Dad’s bedroom. He did anyway, and stuck chewing gum on the wall and left a burned hole in the carpet, according to two people who were there.

When the father found out, he chased Watters out of the house. “I would have killed him if I had caught him, he was so disrespectful,” the father said. (Watters denied the incident ever took place.)

Watters was often dismissive of authority figures, teachers included, multiple classmates said. “He wasn’t very troubled by shame,” the first high school classmate said. 

“It was instantly recognizable, the sort of entitlement, the flippancy, the sort of ego-driven smile,” a third high school classmate said.

He was just one of those people that just sort of sailed through life. Former high school classmate of Jesse Watters

Watters’ time at Friends Academy was cut short his senior year after he and a friend got in trouble for leaving campus during school hours. But the school did not formally suspend or expel Watters. Instead, it allowed him to spend his final semester interning at a publishing company while still receiving his diploma on time. 

Classmates wondered whether Watters’ father’s influence at The Green Vale School, which fed many students into Friends Academy each year, helped him and his friend avoid harsher punishment. “With his father being in that position of power, I don’t know if he ever had to deal with consequence,” the second classmate said.

Watters apparently didn’t seem concerned by how his time at the school ended. “He loved it,” a fourth classmate said. “He thought the whole thing was hilarious.”

The situation was part of a familiar pattern for Watters. “He was just one of those people,” said the third classmate, “that just sort of sailed through life.”

A young Jesse Watters (center) on spring break in Jamaica during college.
A young Jesse Watters (center) on spring break in Jamaica during college.

After high school, Watters attended Trinity College, a liberal arts school in Hartford, Connecticut, just a few hours from Long Island. There, he became friends with a “super alternative” crowd, according to one of his college classmates: “You know, piercings, tattoos.”

Watters registered as a Republican and supported George W. Bush in the 2000 presidential election, but he wasn’t known as particularly political early in college. Most of his political statements were limited to sentiments like “Fuck the government,” said a second college classmate who lived in the same dorm as Watters his freshman year.

“But it wasn’t in a right-wing kind of way,” the dormmate said. Instead, it was in line with the beliefs of Watters’ punk rock friends. 

He wasn’t doing very well ... He was just kind of a mess. Classmate on Jesse Watters in college

During his summers, Watters interned at the New York Stock Exchange. He later joked that he “failed miserably” during his stint in finance because he “couldn’t do basic arithmetic.” But one of Watters’ friends at the internship said he thrived in the social environment.

“It felt like you were in a party all day,” the friend said. “Jesse loved going around and talking to everyone, being charming.” The next summer, however, the two friends got stuck in a cubicle.

“I just remember every day us sitting there being like, ‘What the fuck? They’re making us do spreadsheets?’” the friend continued. “He and I would either go walk around together and go just try to talk to people, hit on girls, look for fucking some action.”

Jesse Watters poses for a photo during his college years.
Jesse Watters poses for a photo during his college years.

At school, Watters’ shamelessness continued ― “He would be the guy that blows smoke in your face for no reason,” the second college classmate said ― and for a period, some of his friends started to worry about him. “He wasn’t doing very well,” his dormmate added. “He was just kind of a mess.”

But toward the second half of Watters’ time at Trinity College, something changed, according to the dormmate and Rajneesh Chellapilla, who lived on the floor above Watters their freshman year. He started to dress nicer. He wore his glasses more often. He became more openly interested in his history classes. His junior year, he interned with Joseph Lieberman, then a Democratic senator from Connecticut.

“From third year onward, it seemed like he matured a lot,” Chellapilla said. “His grades improved.” In 2001, Watters graduated from Trinity College with a B average and a degree in history.

Jesse’s youthful rebellion is being conservative, and he’s never shed it. Former Fox News co-worker

After graduation, he got a job as a production assistant at Fox News. By 2003, he was working for Bill O’Reilly, the host of the network’s highest-rated show, “The O’Reilly Factor.” He worked hard and seemed to buy into the network’s messages. When debating issues like the Iraq War with more liberal members of the staff, Watters sometimes repeated Fox News talking points. When his co-workers met his liberal family, they laughed and wondered where he could have possibly come from, one of his former co-workers said.

“Jesse’s youthful rebellion is being conservative, and he’s never shed it,” the former colleague added.

Watters soon met Noelle Inguagiato, a fellow Fox News employee he would later marry, and cut off some of his harder-partying friends.

“All of a sudden, he was gone,” one of them said. “I could never reach him and we just stopped hanging out completely. I literally haven’t seen him since.”

At “The O’Reilly Factor,” Watters had finally found himself in an environment suited to his personality, and he thrived.

O’Reilly has credited three men with inspiring him to join the media business: sports journalist Howard Cosell, anchor Tom Snyder and Mike Wallace, the famously hard-nosed “60 Minutes” correspondent. “You know, you’re responsible for this O’Reilly deal,” O’Reilly told Wallace in 2007. “I always tell everybody, ‘You’ve got a problem with me? You call Mike Wallace.’”  

Over his career, Wallace, who died in 2012, interviewed some of the most famous names of the 20th century ― Yasser Arafat, Salvador Dalí, Ayn Rand, Malcolm X, you name it. But he also made a name for himself with an innovative type of on-camera interview — one at least partially inspired by the hidden camera show “Candid Camera.”

When Wallace wanted to interview someone who was unwilling to sit down with him, the “60 Minutes” correspondent would sometimes show up wherever the person was and confront him or her with questions. The tactic regularly led to dramatic television moments.

Often, people scurried away and slammed doors in the cameraman’s face. Occasionally, they would also answer Wallace’s questions.

Wallace, who had been a drama major in college, understood the power such moments could have when caught on tape.  “The audience obviously just loved it,” he later said. But eventually, he and “60 Minutes” executive producer Don Hewitt both came to doubt the benefit of such confrontations, which they decided prioritized drama over journalism. “We weren’t getting a lot of information from those so-called ambushes. So we quit,” Wallace later said.

O’Reilly picked up where Wallace left off. And in 2004, two years into his career at Fox, Watters pitched a story to O’Reilly that would forever change the trajectory of his career. The story involved a judge in Alabama who had given a sex offender a light sentence. Watters later remembered O’Reilly telling him, “All right, Watters. You’re going to go down to Alabama and confront the judge.” Watters had never been south of the Mason-Dixon Line at the time O’Reilly gave him the order — much less to Alabama, he said. In his first attempt at an interview, he accidentally mistook a state trooper for the judge.

Watters eventually convinced the judge to do an interview, but he wasn’t sure what to ask him once they sat down, he recalled. “So I tell Bill, I said, ‘Bill, I got this judge. He’s going to talk to me on camera. What should I do?’ And Bill says, ‘When the judge comes out, yell at him.’”

Watters did as he was told, and the judge was “flustered,” he said, making for a digestible television moment that pleased O’Reilly.

Many of O’Reilly’s employees had little interest in performing the confrontational interviews for their boss. Some quietly asked not to do them. But the dramatic moments capitalized on Watters’ shamelessness, turning what was once seen as a fault into a strength.

Watters embraced the “ambush” head on. And in the years after O’Reilly sent him down to Alabama, he confronted Wall Street CEOs, former NSA analysts, newspaper columnists, governors, homeless veterans, school superintendents, and former White House press secretaries. He confronted the New Yorker’s Hendrik Hertzberg, PBS’s Bill Moyers and ThinkProgress editor Amanda Terkel (she is now the HuffPost D.C. bureau chief). 

O’Reilly loved the ambush interviews, and inside “The O’Reilly Factor,” Watters became the closest thing the boss had to a protege. “He knew what direction Bill was looking for,” said Victor Garcia, who worked on the show with Watters for almost eight years. Watters even earned himself a nickname. They called him the “Golden Boy.”

Multiple people Watters interviewed told HuffPost that he appeared disingenuous when he spoke to them, as if the primary tactic wasn’t to obtain information, but to demonize the interviewee to the joy of O’Reilly’s conservative fan base. They described Watters’ interview tactics as “slimy” and “condescending.”

But “Factor” employees appreciated what made Watters so effective on television: He didn’t appear to be attacking his subjects. Instead, he smiled and smirked.

You’re never afraid out there, are you?” O’Reilly later asked Watters on air.

“No, I’m just afraid to come back empty-handed for you,” Watters replied.

“That’s the secret,” said Joe Muto, who worked on “The O’Reilly Factor” from 2007 until 2012, when Fox News fired him after discovering he had been anonymously writing about life at the network for Gawker. “When you come at them angry, it’s scary, it’s intimidating and it makes the viewer sorry for the ambush subject. Whereas if you come at them with a smile and you’re kind of funny about it, that makes for better television.”

Often, Watters got good reactions from the Fox News audience just because of the way he looked — tall, handsome and white, in a suit or a polo shirt with a popped collar and his hair just so, said one of his former co-workers. “He is the type of young man whom white America wants their daughter to bring home,” the former colleague said. “If you’re a Long Island conservative, you couldn’t dream of a better son-in-law for your daughter to bring home than Jesse Watters.”

If you’re a Long Island conservative, you couldn’t dream of a better son-in-law for your daughter to bring home than Jesse Watters. Former colleague of Jesse Watters

At the office, Watters was well-liked by co-workers of all political persuasions. He loved Top 40 music, often filling the role of office DJ. He liked to talk about ABC’s “The Bachelor.” Unlike most of his colleagues, he usually dressed in a suit and tie, but he didn’t take himself incredibly seriously. ”In our years of working together, I don’t recall ever seeing him angry or out of sorts,” said a former “Factor” producer.

Even if Watters often spouted Fox News talking points when out with more liberal coworkers, Muto considered Watters one of the more fun conservatives at the network. 

“There are some people at Fox who are Kool-Aid drinkers and are completely insufferable and want to, like, buttonhole you and tell you why poor people are freeloaders,” Muto said. “Jesse wasn’t like that. He was funny, and you had the sense that he was relatively self-aware and [knew] Fox News was just catering to idiots. Because he wasn’t a total Kool-Aid drinker, he would kind of acknowledge sometimes the ludicrousness of the conservative positions.”

Publicly, O’Reilly defended Watters’ ambush interviews ― which often took place outside the subject’s home or workplace ― like Wallace once did, as “a vital tool in holding public servants accountable for their actions.”

“When the bad guys won’t comment, when they run and hide, we will find them,” O’Reilly said. Fox News also insists that “The O’Reilly Factor” almost always made an earnest attempt to bring people in as guests before Watters ambushed them.

But that was often not actually the case, Muto said. Oftentimes, there was only a token attempt to contact ambush victims beforehand, and it was “usually disingenuous,” Muto said. The real point, “Factor” employees inherently understood, was to make their subjects look foolish.

“The secret of the ambush interview is that the ambush interview almost always makes for good TV. No one looks cool and poised on camera,” said Muto. If you say ‘No comment’ and walk away, that’s great video. If you stop and you argue with Jesse, that’s great video [too].”

Watters has said that O’Reilly told him to be “polite, respectful and succinct” when ambushing people. But back at Fox News, the directives sounded different. Owen Brennan, who worked on “The O’Reilly Factor” for about two and a half years, said that Watters and O’Reilly could be seen together at work “just sort of like war-gaming every interview that Jesse did.”

Some of O’Reilly’s ideas in particular stuck out. “One of the first times, [O’Reilly] said, ‘When you talk to someone, get your foot in the door,’” Brennan said. “So they can’t close the door on you.” Watters ended up using variations of that tactic multiple times, including while confronting Hampshire College President Jonathan Lash at the door of his home.

Lash called the cops. Later, Hampshire College said in a statement that “[Watters] did not request an interview but rather entered private property and then tried to prevent the president of the college from entering his private home.”

A few weeks later, while discussing the incident, Watters said, “There are heroes and villains out there in the media landscape, in the news landscape, in the political landscape. People sometimes get called out, they react how they react. And I’m proud of what I do.”

Wallace, who had popularized the technique that helped make Watters famous, did not share Watters’ sense of pride in it. I have no doubt that what we started has become a plague,” he told Howard Kurtz on CNN in 2006.

I have no doubt that what we started has become a plague. Mike Wallace in 2006

The ambush interviews got Watters out into the field. But his time on “The O’Reilly Factor” came to be defined by segments of a related but slightly different variety.

A year after Watters went to Alabama for his first ambush interview, he pitched a story to O’Reilly about a sex-positive party at Brown University called “Sex Power God” that was sponsored by the school’s Queer Alliance.

To all of our horror, Bill says, ‘Yeah, go up there and cover it,’” Brennan said. In Rhode Island, Watters paid roughly $80 on the internet for a ticket and entered the party without identifying himself as a Fox News journalist. He and a producer then took video of half-naked undergraduates dancing together without obtaining their consent.

The first thing I saw was just pure debauchery,” Watters later told O’Reilly on air. “Girls were falling down drunk all over the place ... There was guys kissing guys, girls making out with girls … it was the wildest party that I’d ever been to.”

At Brown University, there was a fear that the Watters’ segment might accidentally out some of the students to their conservative relatives.

But at Fox News, the “Sex Power God” segment was seen as a success, and an indicator that Watters could be just as successful investigating the lives and opinions of regular Americans.

So over time, Watters started to occasionally drop the ambush interview in favor of an easily repeatable format familiar to fans of Jay Leno’s “Jaywalking” bits. In these segments, Watters interviewed people in public, hoping they’d say something inaccurate or do something dumb. But Watters’ version of “Jaywalking” differed from Leno’s in one unmistakable manner: Watters’ man-on-the-street bits almost always played off of conservative stereotypes — especially those revolving around the young, educated, liberal or drug-using. 

“One of Bill’s talents was sort of finding these fault lines in topics where you’d be able to split the audience and get people on both sides [interested],” Brennan told HuffPost. “[Watters] has picked up some of the skills that Bill had, as far as identifying these cultural fault lines.”

Over hundreds of segments, Watters depicted Ivy League students as pretentious and entitled. He made the homeless look like drug-addicted freeloaders and asked if he could hold a “straight pride parade.” He mocked the notion that men shouldn’t be able to compliment a woman’s physical appearance at work. He marched around Boston in snow dismissing the threat of global warming (“If the Earth starts to cool, would we get less snow?” he asked). When a student at the University of Missouri told Watters that “a swastika was painted on someone’s door in human feces,” Watters belittled what could have been seen as a hate crime by yelling, “Poop swastika!” 

After Watters created a segment mischaracterizing Dearborn, Michigan, as a place where Muslims commit honor killings and stone women, people called for the city to be bombed, leading Dearborn’s mayor to send a letter to O’Reilly calling the piece factually inaccurate and harmful. When a group of high schoolers in Vermont criticized a segment that depicted their state as a hotbed of left-wing lunacy, he responded with a video in which two female high school students’ comments were followed by a “Dazed and Confused” clip in which Matthew McConaughey says, “That’s what I love about these high school girls, man. I get older, they stay the same age.”

In January, Watters’ mother, Anne, wrote her son an impassioned note explaining why she and the rest of the family had decided to attend the upcoming Women’s March in Washington, D.C., which took place largely in opposition to President Donald Trump’s policies.

“My hope,” she wrote, “is that the event will make a strong national statement about our collective belief that we cannot espouse discrimination of any sort — toward anyone anywhere.”

Watters read his mother’s note on air. Then he rolled tape on a mocking segment about the march.

Watters has said that he hopes to make his interviews comfortable for his subjects. “I try to make it enjoyable for the person I’m interviewing. We always come away from the interview all smiles, for the most part,” he said in 2015.

The interview subjects disagree. “That was not the case — for me or for anybody else that he interviewed,” said Natalia Maymi, whom Watters interviewed at Brown University in 2013.

And the country’s foremost ambush interviewer has not appeared to enjoy the few instances when others have tried to interview him. When ThinkProgress’ Ben Armbruster asked Watters at CPAC about Fox News’ right-leaning bias, Watters, smirking and visibly annoyed, responded by calling Armbruster “JV” and telling him his question and use of a camera phone were both amateur. “Watch my blazer, bro,” an irritated Watters said at one point.

When comedian Jason Selvig confronted Watters in New York City shortly after the Chinatown segment premiered, Watters, again smirking and visibly annoyed, refused to answer questions while Selvig followed him as he tried to walk away. And when Ryan Grim, who ran HuffPost’s D.C. bureau until earlier this year, attempted to film Watters at the after-party of the White House Correspondents’ Association dinner, Watters took the phone out of his hands, and a confrontation ensued.

HuffPost repeatedly tried to speak with Watters for this article. Although he’s made a career out of forcing others into interviews, he refused to do one with us. He declined an interview through a Fox News spokesperson.

It’s unclear what Watters was hiding from. Perhaps his previous run-ins with current and former members of the HuffPost staff spooked him. But maybe he was worried about the timing. We first spoke to Fox News in May — less than a month after Watters’ move to “The Five” and just a few weeks after he joked during the show that he “really liked how [Ivanka Trump] was speaking into the microphone” while making a gesture that some viewed as miming oral sex.

Soon after, Watters went on a brief vacation that many saw as an unannounced punishment. The episode followed a familiar pattern for the “Golden Boy” — behave badly, get off easy.

CORRECTION: A quote from Owen Brennan regarding O’Reilly’s ability to identify cultural fault lines has been updated to correct a transcription error, which initially suggested he tried to “spook the audience and pit people” against each other.

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