The reinvention of Greg Kelly from charismatic New York insider to firebrand Trump booster

July 2024 · 19 minute read

The day after thousands of rioters ransacked the Capitol in an attempt to overturn the results of the presidential election, Greg Kelly was disgusted. Except his ire was not directed at President Donald Trump, but at President-elect Joe Biden. 

"Sometimes, sometimes the bank robber gets away with it," Kelly fumed from his anchor chair at Newsmax. "Joe Biden stole the election. You know it. I know it. Tens of millions of Americans agree with us."

"Donald Trump should not concede because he didn't lose," Kelly continued, in a monologue. "But we do recognize this, that come noon on Jan. 20th, Donald Trump will no longer be the president. Because Joe Biden got away with it." 

Viewers may remember Kelly as the jocular co-host of Fox 5's morning show Good Day New York for nearly a decade while his father Ray Kelly ran the NYPD under Mayor Michael Bloomberg. Or they know him as the Fox News Channel's war reporter, who was among the first to broadcast live from Baghdad with a U.S. Army brigade in 2003. Or, they recognize him as the New York media personality frequently lampooned by Gawker who successfully averted a rape charge when the DA decided not to file but then seemed to disappear from the scene.

Now Kelly is the face of Newsmax, a fringe cable network now carried in 70 million homes that has leveraged broadcasting electoral conspiracy theories to win viewers in the increasingly balkanized conservative audience. On one night in December, Kelly's show nipped his competition on the mighty Fox News Channel by 26,000 viewers in the key demographic of 25- to 54-year-olds. Friends of Kelly have been stunned by his transformation and say they barely recognize the firebrand anchor who has clung to Trump's baseless claims and echoed the president's vitriolic tirades against the "fake news." 

"Either Greg believes it or Greg is being a good soldier, which he's always been, and he's doing what his bosses are telling him to do," former Fox executive Robert Zimmerman said. "When he was at Fox he always wanted to do the right thing by his bosses."

Or, as John Catsimatidis, a conservative talk radio host who recommended Kelly for the Newsmax job, put it: "Maybe he got offered a deal he couldn't say no to."

On Newsmax, Kelly is the plainspoken outsider railing against the hubris of media elites. But the broadcaster owes his longevity in journalism to family and political connections. He has also been incredibly lucky. He was lucky to get hired by Fox News and tapped to be a local morning anchor when its then-CEO Roger Ailes was friendly with his father. He was lucky to get another gig in cable because the company's CEO was revamping its lineup. And he was lucky Donald Trump liked him and promoted his show.  

Trump will soon leave office but Newsmax has become devoted to promoting the reactionary forces that backed him. Kelly has become a vessel of right-wing fury perpetuating a false political myth with deadly consequences, and his audience is only growing.

A POWERFUL FAMILY

Kelly has the look of someone born to sit in an anchor chair but his father Ray Kelly's legacy of public service has loomed throughout his life. He partly owes his camera-ready looks to his father too. Both men share long prominent foreheads abutted by a receding hairline, deep-set Irish eyes, and a sharp jaw. But Greg is looser in public than the police chief, his face often contorting into an aw-shucks smirk.

His father always seemed to be chasing his destiny, fighting with the Marines in Vietnam, rising through the ranks in 25 different commands of the NYPD before serving as police commissioner, twice, under Mayors David Dinkins and Michael Bloomberg.

Greg Kelly (center) with his parents, Ray and Veronica Kelly, in 2017. Eugene Gologursky/Getty Images

Greg Kelly's journey has been more circuitous. He grew up in Garden City, a dense Long Island suburb near the Queens border. After majoring in political science at Fordham University, where he also worked at the school's FM radio station WFUV, Kelly followed his father's path into the Marine Corps. "It wasn't The Great Santini 'You will do this!' or anything like that. It really was leadership by example," Kelly told WNET's Steve Adubato in 2016. "I wanted to have the experience he had. I saw what it gave him or I saw what it made him, and I wanted to do it too."

Kelly learned to fly Harrier jets in Yuma, Arizona, and deployed to the Persian Gulf in 1998 to enforce a no-flight zone over southern Iraq. After nine years, he was ready for something new but unsure of what that might be. He credits his older brother for suggesting he pick up his college interest in journalism. By then, his father had served as police commissioner under Dinkins, New York City's first black mayor, and had just landed in the Clinton White House as U.S. Customs Service commissioner. Greg Kelly scattered resumes across the country until an ABC affiliate in Binghamton, New York, hired him to be a reporter. He quickly made a name for himself, scoring an on-air interview with President Bill Clinton. 

Within a year Kelly had moved on to NY1, a 24-hour cable news channel covering New York City's five boroughs, and was assigned to cover City Hall. Station manager Steve Paulus remembered asking Kelly how he would feel sparring with the city's combative, operatic mayor Rudy Giuliani, who had defeated Dinkins in 1993 by excoriating the police response, under commissioner Ray Kelly, to the Crown Heights riot

"I asked Greg, 'You're going to be in the Blue Room at City Hall and ask tough questions. Does that faze you at all?' And he said, 'Listen, I crashed a $15 million aircraft carrier jump jet so asking a question for Rudy doesn't bother me.'" Paulus told Insider. "It was the most interesting response in a job interview I ever got." (These days, Giuliani appears regularly on "Greg Kelly Reports." Greg Kelly declined repeated requests to speak to Insider for this story.) 

After the 9/11 attack, he reported from the smoldering pit of the World Trade Center every day for weeks. 

While covering the mayoral campaign of billionaire media mogul Michael Bloomberg, who would follow Giuliani into City Hall and make Ray Kelly the city's police commissioner for a second time, several colleagues described Kelly as a "rabid" supporter. Paulus recalled him as a "pretty standard, straight down the line" journalist, but said Kelly had trouble receiving feedback. One time Paulus shared a viewer's email that described an interview he had done with Bloomberg as "insipid." "Why didn't he ask tougher questions?" the viewer wanted to know.

"Greg got upset with that and sent me an email, 'If your goal wasn't to demoralize and humiliate me you did,'" according to Paulus. "He didn't talk with me after that until he left. It was very weird."

But by then Kelly seemed to be leaving local news behind. Fox News CEO Roger Ailes was friendly with Ray Kelly and a reel of Greg's work reached his office, Fox sources said. A little over a year after 9/11, Kelly joined Fox. And when Congress authorized President Bush to declare war against Iraq, network executives saw Kelly as an ideal embed. A month later, in December 2002, the ex-Marine accompanied the U.S. Army's 3rd Infantry Division to the Middle East. 

The assignment was harrowing. A mortar attack shattered his camera lens and bloodied his face when the brigade was trying to secure a bridge. 

Kelly became the first television reporter beaming live images of American tanks speeding into Baghdad in April 2003. "I want these guys to win," he told Newsday. "I try to correct myself in the live shots when I say 'we,' but I slip all the time. I'm not objective. Yeah, I want these guys to win." When he entered Saddam Hussein's palace with U.S. troops two days later, he described it, memorably, as "not the palace that Architectural Digest would feature."

Kelly's combat coverage landed him a promotion to White House correspondent, but he didn't mesh with the station's clubby Capitol bureau and his performance suffered, Fox officials said. "Greg wasn't Britt [Hume] or Brett [Bair] people who moved up the D.C. ranks for Fox," Zimmerman said. "The crew down there preferred the people they trained."

Ailes tried him in another slot as a weekend anchor on Fox & Friends in June 2007. But ratings for weekend morning shows were low — some executives put the number at 700,000 viewers — and Kelly's presence did little to jolt viewership.

"We tried him in a bunch of different roles. It didn't work. Something was off," a Fox official told Insider. "Viewers didn't like him that much."

But Ailes apparently didn't want to part ways. Instead, he sent Kelly back to New York and gave him an anchor slot on Fox 5's Good Day New York. The morning show's ratings had been slipping but still commanded a higher viewership than Fox News's weekend programs. Suddenly Kelly had an even larger audience in the city where his father was its second biggest newsmaker.

Station managers paired him with Rosanna Scotto, a charismatic evening news anchor, and Fox splurged to promote the pair on bus and subway ads throughout the city. The first two hours the show followed the news of the day while the third hour covered entertainment and included funny skits with costumes. The pivot from hard to soft news was an adjustment, but both hosts found its breezier format suited them.

"He was a great conversationalist. It's a hard thing to do when you're getting up at 4 in the morning," said political consultant William F. B. O'Reilly. "He and Rosanna had a great banter. It was definitely a show you want to have clients on."

Greg Kelly had found his way. 

"KING LEER" 

It so happened that Kelly's rise as a local media star coincided with the heyday of audacious New York media reporting. Kelly, with his seemingly easy success and awkward performances, especially with female guests, was an obvious target. The New York Observer and Gawker mercilessly documented Kelly's faux pas, including one segment when he asked for details showing Erykah Badu performed naked in her music video, another when he requested a closer look at a model's shapewear, and one where he had a coughing fit after biting his nails.

Rosanna Scotto, Greg Kelly's co-host (left), with NYPD Commissioner Ray Kelly (center) and Greg Kelly at a gala in 2009. Ben Gabbe/Getty Images

As Foster Kamer, an editor who covered Kelly's antics for The Observer, told Insider: "What is this decorated ex-Marine who's done big cable news moments doing by playing the dumbest version of himself on local morning news? What is he aspiring to?"

No outlet mocked Kelly with more ferocity than E! Television's The Soup. When Kelly finally departed Good Day, host Joel McHale spliced a highlight reel of Kelly's quips glaring at guests, identifying a dog's penis, and repeatedly demanding B-roll of Burger King's suburban corporate headquarters.

Kelly seemed wounded by the attention but the Good Day anchor soon had more serious problems beyond someone poking fun at him. 

On Jan. 25, 2012, Manhattan District Attorney Cy Vance's office began investigating an accusation that Kelly had raped a woman in her Wall Street law office the previous October. (The case was referred to Vance's office after the police department, headed by Kelly's father, recused itself.) The woman told police she became pregnant from the encounter and had an abortion. It also came out that the woman's boyfriend had confronted the commissioner at an event and told him about the incident. The accusation against the police chief's son was immediately a huge news story. Just two days before the news broke, Vance had appeared on Good Day New York and Kelly had pressed him on his decision to drop rape charges against former International Monetary Fund manager Dominique Strauss-Kahn. 

Vance's office investigated and within two weeks announced there would not be charges against Kelly because the "facts established during our investigation do not fit the definitions of sexual assault crimes under New York criminal law."

Three days later, Kelly returned to the air. And then, he was back to his banter and silly morning-show bits with his co-host.

Greg Kelly, Police Commissioner Ray Kelly and Fox News mogul Rupert Murdoch in 2010 in New York City. Billy Farrell/Getty Images

Kelly was widely seen as having weathered the storm. He had brought in publicist Ken Sunshine, a friend of his father's whose firm had experience managing celebrity crises, and news coverage of the accusations had been skeptical. A New York Post report asserted the DA's office doubted the woman's account and branded her "Shady Lady" on its cover. Other outlets scrutinized the woman's behavior. "He got very good press," one former co-worker said of Kelly. "Ken Sunshine did a great job getting his side out there." But some saw the episode as cementing Kelly's feelings as an outsider and his own distrust of the mainstream media. 

"People who have been through any news cycle feel maligned by the mainstream media and can transfer it to other experiences," Kelly Nicole Hemmer, a Columbia University historian who studies conservative media, told Insider. "Media criticism is part of what it means to be a conservative and a conservative media personality."

As Kelly's gaffes continued, so did the ridicule. A media narrative had already been established that Kelly was "the fratboy extraordinaire of local morning TV who grew up as Ray Kelly's kid"  Kamer, The Observer editor, told Insider. During one segment in June 2014 promoting New Jersey's Action Park, bikini-clad reporter Anna Gilligan zip-lined into a pool of water. "First of all, nice bathing suit," Kelly interjected, before Scotto could shush him with a warning to "stay appropriate." The New York Daily News scolded Kelly with the headline "King Leer" and wrote that he had gone from Fox, "to pig."

Fox ousted Ailes in July 2016 amid multiple sexual harassment allegations and network executives began purging employees he liked. When Kelly's contract expired in September 2017 the station declined to renew it. 

As one network insider said: "Fox got rid of Roger's friends. Everyone who wasn't a top performer was kept on in their role because of family relationships with Roger. Fox was trying to go in a different direction after Roger left."

It seems Kelly's luck had run out. He was back on the job market.

"IT ISN'T OVER YET" 

In the summer of 2019, Kelly ran into Chris Ruddy at a party on Long Island. The Newsmax CEO started out a reporter for the New York Post writing about the suicide of former Clinton administration attorney Vince Foster before founding a conservative-leaning website in 1998 with an investment from far-right donor Richard Mellon Scaife. 

The Florida-based media company, whose channel appears in the 200s and 300s on most TV dials, had broadcast out of a ramshackle 40th Street studio before quadrupling its space in 2019. The company invested $70 million into the station from 2014 to 2017 and added talent including pundit Mark Halperin, who had disappeared from mainstream news outlets after at least a dozen former colleagues accused him of sexual harassment, and former White House Press Secretary Sean Spicer. But Newsmax currently loses money. The station brought in an estimated $25 million in revenue last year but faced $27.9 million in operating costs. 

Ruddy was familiar with Kelly's work from Iraq and had run into Kelly at social events a half-dozen times prior to 2019. He liked Ray Kelly, but the two were not well acquainted.

Newsmax Media CEO Christopher Ruddy attends a dinner with the US president and business leaders in Bedminster, New Jersey, in 2018. Brendan Smialowski/AFP via Getty Images)

"I thought he was good on television," Ruddy told Insider. "His father was well-liked and well-respected in the city of New York on both sides of the aisle so I figured he would be something like his father — a guy who is respected because he has a lot of integrity."

The pair spoke about how the media didn't understand Trump and Kelly expressed an interest in joining Newsmax.

"I wasn't hiring him on a political litmus test. I was hiring him on the force of his personality, his interest in news, his experience in analyzing news," Ruddy continued. "It surprised me he was more conservative than I thought."

Ruddy also received recommendations from several people who knew Kelly, including John Catsimatidis, who recently purchased WABC radio. "I know his dad. He left Fox 5 and Newsmax was building a team," Catsimatidis said. 

Despite his time in Washington and trailing the New York City mayor, Kelly has long insisted he dislikes politics. "No, I don't like politics particularly," Kelly told Adubato. "I was something of a political junkie but I kind of lost my taste for it and I think it has helped me as a talk show host." 

Few seemed to know his personal politics. Friends described him as privately conservative while others saw him as a centrist. Kelly met privately with political consultants while his father considered a 2013 mayoral run as a Republican but he once contemplated challenging Manhattan Congresswoman Carolyn Maloney in a Democratic primary, sources said. His 2017 wedding featured prominent members of both parties including former Democratic Mayor David Dinkins who officiated the ceremony. (Kelly's wife, Judith Grey, was briefly a contributor to Business Insider.) 

But his career had stalled at a time when the media industry was becoming more polarized. He developed an opinion-based show showcasing bias in the mainstream media and pitched the idea to producers in Hollywood but wasn't able to sell it. A Fox News spokeswoman said Kelly did not approach anyone at Newscorp.

"Greg Kelly Reports" launched in January opposite Fox's Martha MacCallum at 7pm. (Newsmax won't say how much he gets paid but sources snarkily opined that he may only be earning $100,000, roughly the equivalent of a senior reporter for a wire service. Newsmax declined to discuss Kelly's compensation.) At first, Kelly pledged that curiosity would be a core value of his show and his producers booked both Democrats and Republicans. When the mysterious pneumonia was spreading across China in January, Dr. Anthony Fauci was a guest

"There was a bit of a transition from him," Ruddy said. "He came from the morning show and that tends to be a cheery, happy talk, conversational-time program. We wanted a news edge on the program but Greg can be very disarming and charming."

Newsday was the only outlet to cover his career move. "I do feel more comfortable expressing my opinions and feel they're more valuable now," he told the Long Island paper. 

He sharply questioned Pete Buttigieg's military experience in a Wall Street Journal editorial which some friends thought was hypocritical for someone who leveraged his own Marine Corps training. 

He also fawned over Trump, whose June 2015 campaign announcement at Trump Tower he attended along with Scotto, and believed Trump would win re-election.

"Greg was always very pro-Trump. He's a big fan of Donald's," Sam Nunberg, a former Trump campaign aide and a regular guest on Newsmax, told Insider. "I was on his show in May when Trump was down 10 points and he was saying Trump was going to win."

Ratings remained minuscule. Newsmax garnered only about 21,000 viewers during a week in the summer compared with Fox's 1.9 million, according to the Washington Post.

As the election grew nearer Trump officials began appearing regularly on Kelly's show and Kelly scored a friendly interview with Trump on October 14 where Trump railed the election was "very rigged" because of mail-in ballots and he was prepared to fight the results.

But then came election day. Fox News's decision desk called Arizona early, and on Friday the anchors on Fox and Friends reported that Biden nudged ahead in the Pennsylvania vote count. Trump was livid, and so were his millions of loyal supporters. When Fox News officially called the election for Biden, Trump tweeted three Newsmax clips in three minutes on November 9 including one with a graphic, "IT ISN'T OVER YET." 

—Greg Kelly (@gregkellyusa) January 13, 2021

 

Suddenly viewers began to tune into the insurgent cable station. Newsmax averaged 182,000 viewers per day during the week of the election but the following Monday ratings nearly doubled to 347,000 viewers and soared to 437,000 viewers on Tuesday, CNN reported.

Kelly's show brought in the network's highest ratings with 700,000 to 800,000 viewers on those days. The following month, Kelly beat his competition at Fox in the 25 to 54 demographic with 229,000 viewers to Martha MacCallum's 203,000 viewers, CNN reported.

"Greg was a bit of a phenomenon before Election Day and it's really surged since then," Ruddy said. "Considering we don't even have our full program lineup and considering handicaps the new network has we're doing amazing stuff."

With Trump now acknowledging Biden will be sworn in on Jan. 20, the conservative media war is now in full swing. Fox has said it plans to add an opinion show at the 7 pm slot, opposite Kelly, and move MacCallum to midday. The One America News Network is also gunning for Trump supporters who may be looking for an alternative to Fox. And Trump, not to mention his family, has been mum about his plans after he leaves the White House. 

Some of Kelly's associates openly wonder if he will reinvent himself yet again. 

"He looks a little bit shrill repeating Trump's line. That doesn't suit him," former New York Republican Party chairman Ed Cox told Insider. "He's not a natural ideologue. He's a thoughtful guy. As Trump fades, it could play into Greg's strengths."

Ruddy meanwhile has tried to raise $300 million to invest in the network, a source said. He also tried recruiting Fox's Laura Ingraham and Jeanine Pirro and both turned down his overtures, the source added. 

But the opportunity to appeal to millions of alienated conservative viewers remains. 

"Newsmax has the greatest capacity on TV airwaves to keep the Republican Party the party of the working class," Nunberg said. "They can hit numbers and those carriers care about one thing — eyeballs and money. And Newsmax is going to get a lot of eyeballs and generate a lot of money for a lot of people."

Last December, the New York Times media columnist, Ben Smith, reported that the vote processing companies Smartmatic and Dominion Voting Systems were threatening right-wing media, including Newsmax, with lawsuits over false and baseless claims made about them on air. Within hours, Newsmax's John Tabacco was on air reading a lengthy statement to "clarify" the network's reporting on the 2020 election results.

But if Newsmax is toying with a new approach, Kelly has continued to use his show to air the president's grievances, and the far-fetched plans of his loyal supporters. 

A few days after the siege at the Capitol, and just hours after Congress impeached Trump for inciting the insurrection, Kelly welcomed Georgia congresswoman Marjorie Taylor Greene who promised she would file articles of impeachment against Joe Biden on January 21, the incoming president's first full day in office. 

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