One night last month at Mar-a-Lago, Chris Ruddy positioned himself in a familiar spot: right next to Donald Trump.

The occasion came just days before a Republican National Committee fundraiser, one of many such events popping up at Trump's Florida properties in his post-presidential life — a time when it has become easier for Ruddy to secure such proximity. During Trump's four years in the White House, aides had grown suspicious of the conservative media entrepreneur's presence and his tendency to bring friends, clients and allies to the private Palm Beach club to make an introduction. At one point, White House Chief of Staff John F. Kelly went so far as to insist that more-senior White House officials accompany Trump to Mar-a-Lago to temper his interactions with members such as the Palm Beach-based Ruddy, whose Newsmax cable news channel has attempted to challenge Fox News from the right.

That night in April, Trump was riffing for his audience, and Ruddy was at the next table, facing the lobster station. Trump lamented that removing the shells made a $200 lobster look like a $2 lobster and mused that he should tell his staff to serve them in their shells to better impress diners.

A bit of showmanship that Ruddy might relate to.

Newsmax’s visibility rose during the Trump era in no small part because Ruddy’s did. In numerous news stories that were often built on the accounts of unnamed Trump aides and allies, Ruddy was the rare associate willing to lend a colorful quote with his name attached. Through sheer ubiquity — and a strategically public presence at Trump’s clubs — he cultivated a brand name as a Trump “insider” — though advisers to the former president maintain Ruddy was never as close to the man as he led people to believe.

Along the way, he presented an image of his small television operation as a David poised to overcome the Goliaths of cable news — and perhaps even join forces with the Trump family.

Yet Ruddy’s attempts to attach himself to Trump, and ingratiate himself with Trump’s base, have landed him in legal jeopardy. Far more so than Fox, Newsmax promoted Trump’s lie of a stolen election, and carried on with that message through and beyond Jan. 6, when a violent mob stormed the Capitol.

Now the most quotable man in Trump’s orbit is keeping his head down, as his company faces the threat of potentially disastrous lawsuits from voting technology companies that claim they were defamed by Newsmax’s copious spewing of baseless election-fraud claims. Ruddy declined repeated interview requests for this story.

Long before the Trump era, Ruddy was best known as the young New York Post reporter probing the 1993 suicide of Clinton White House aide Vince Foster — and exploring the wilder, false claims that he had been murdered. His work made its mark: Brett M. Kavanaugh, then working for Kenneth Starr's investigation into the Lewinsky affair, circulated Ruddy's articles to lawyers who joined the team.

Friends and colleagues from his younger days wouldn’t easily peg Ruddy as a right-wing firebrand. He had a short stint as a Bronx public high school teacher — even serving as the chapter chairman of the teachers union — before moving on to edit a short-lived conservative monthly, the New York Guardian, where he wrote pieces questioning whether a school’s anti-drug program paid homage to “drag queens.”

At the New York Post, though, Ruddy proved to be a pioneer of America’s looming misinformation complex — making a name for himself by pushing stories that badly lacked substantiating evidence. The officer who found Foster’s body sued him over a story he wrote alleging that National Park Police officers staged the lawyer’s death.

The suit was eventually dismissed, but that kind of coverage helped him get a job in 1995 at the Pittsburgh Tribune-Review, owned by Clinton critic and conservative financier Richard Scaife. Two years later Ruddy got a deal to write a book titled “The Strange Death of Vincent Foster.”

But after a ragtag Internet site called the Drudge Report began racking up scoop after scoop on the Clinton-Lewinsky story, Ruddy and other conservative journalists took notice of the growing new medium. In 1998, when he was 33, Ruddy launched Newsmax, initially a website, with Scaife’s backing.

In those early money-losing years — including $8.1 million down the drain from 2000 to 2001, according to securities filings from an ill-fated effort to take Newsmax public — about half of Newsmax’s revenue came from merchandise sales. Among its offerings were Patrick Buchanan’s book, “Death of the West,” Bush Country T-shirts and USS Ronald Reagan baseball caps. Later, Ruddy marketed a set of playing cards dubbed the Deck of Weasels, mocking antiwar figures such as Michael Moore, Susan Sarandon and French President Jacques Chirac.

“I think we all understand that journalism needed to find alternate sources of revenue,” said Jennifer Bertetto, president of 535 Media, a digital marketing agency started by Scaife that once controlled a stake in Newsmax, “and he was really ahead of that.”

Yet Newmax’s core business model would eventually be centered on email marketing. Visitors to the site — primarily older readers — would log on to certain features by entering an email address that Newsmax would then use to market Ruddy’s other businesses, selling annuities, life insurance, investment products and newsletters. The company currently offers nine finance newsletters and five health-related ones.

“That’s where all his power and money come from,” said a Newsmax television host, who spoke on the condition of anonymity to avoid alienating the boss.

The newsletter business begot books targeted to “real” or “heartland” Americans — titles such as “Fight Back: Beat the Coronavirus” and “Blitz: Trump Will Smash the Left and Win” — as well a line of vitamins and dietary supplements.

It was unglamorous stuff. But it paved Ruddy’s path into higher levels of politics, as Republican operatives began tapping into his data-rich email lists to target potential voters. Between 2013 and 2020, more than a dozen campaigns or PACs paid Newsmax to rent email lists or use them for fundraising or solicitations, even as Newsmax’s journalism operations covered their campaigns.

Trump’s campaign was an early adopter, spending more on Ruddy’s lists than any other candidate, paying Newsmax $201,073 for a series of “list rental” buys, according to 2016 campaign finance filings.

“Newsmax played a more influential role in the rise of Trump than any other outlet,” said Sam Nunberg, an early campaign adviser, who noted that the campaign raised at least $800,000 from the fundraising solicitations it sent out. “Because Newsmax is TV, print and digital, it could get people everywhere.”

Sen. Rand Paul’s campaign spent $27,750 on Newsmax lists for his 2016 Senate reelection in Kentucky, while Carly Fiorina’s presidential campaign paid the company $6,089 that same cycle.

It didn’t always work so smoothly. In 2014, former senator Scott Brown (R-Mass.) severed his relationship with Newsmax after it blasted people who had signed up for his email list with a message titled “5 Signs You’ll Get Alzheimer’s disease.” Through a spokesperson, Brown declined to comment.

Though Ruddy is not a registered Republican, the Long Island native was drawn years ago to South Florida, like many conservatives, by the lack of a state income tax and the presence of right-wing heavy hitters such as Ann Coulter and Rush Limbaugh.

There, he socialized aggressively. When he first joined Mar-a-Lago, it was at Trump’s invitation, former aides say, partly for the social introductions that Ruddy could make for Trump in conservative circles.

And then Trump ran for president. And Ruddy was fully on board.

Newsmax even capitalized on the campaign by selling Make America Great Again hats, said Bertetto, adding that this displeased the candidate, who was marketing similar products. “I think he told him he needed to stop.”

But as Trump rose in the polls, he pulled Newsmax and Ruddy along with him. Suddenly, Ruddy was more famous as a friend of the president than he was as CEO of Newsmax.

Ruddy was generally ready with a quote about Trump, one of the few people willing to go on the record about the mogul. That stance gave Ruddy added credibility with reporters, who cited him liberally in their stories about the president’s state of mind. When Trump pulled an upset victory, Ruddy turned their relationship into another lever of influence.

Ruddy frequently brought reporters to Mar-a-Lago and introduced them to Trump, as well as guests such as Alan Dershowitz and business executives who wanted to meet the president. Ruddy would learn the president’s schedule, figure out where he was going to sit and make sure he had the nearest table to him, several former Trump officials told The Washington Post.

He also lobbied the White House to block a proposed merger between two major owners of local TV stations, Sinclair and Tribune, which might have resulted in Sinclair turning Tribune’s WGN basic-cable station into a right-leaning cable network to rival Newsmax.

Ruddy frequently brought up other policy issues with top aides and the president. Ruddy’s memos that he shared with the president advocating specific legislative or policy points were so frequent and so detailed that some White House aides suspected he was getting paid to put them on Trump’s radar. Ruddy denies that he was ever paid to mention anyone in a memo or conversation.

“I never requested or accepted money from any person or organization for any purpose relating to any memo I wrote to the President, for any contacts I had with the President, or any other government official with whom I may have interacted,” Ruddy wrote to The Post in an email.

Meanwhile, Newsmax’s TV channel, launched in 2014, turned a perpetually favorable lens toward Trump. When the rest of the media world recoiled from the president’s swipe at MSNBC anchor Mika Brzezinski — he said she was “bleeding badly from a facelift” — Tom DeLay appeared on Newsmax to praise the president. “I am so glad he’s going after the media and going after them in a personal way, because they’re going after him in a personal way,” the former congressman told the channel’s Steve Malzberg.

After Fox News's controversial but accurate election-night projection that Biden would win Arizona enraged the president and his base, Ruddy sensed a business opportunity.

Newsmax championed the quickly discredited election fraud claims promoted by Trump and his attorneys, Sidney Powell and Rudolph W. Giuliani — and then Trump, in turn, lavished praise on Newsmax while publicly castigating Fox.

In interviews shortly after the election, Ruddy denied that Newsmax believed election fraud had happened; rather, he argued that viewers could decide for themselves after hearing arguments from all sides.

But its ratings surged. A particular bright spot came courtesy of a former Fox News personality Greg Kelly, whose 7 p.m. Newsmax slot reached barely 100,000 viewers before the election but nearly 1 million for a short period afterward. For one night, Kelly even beat Fox’s Martha MacCallum by a hair. And Ruddy made sure everyone knew it, circulating ratings data for his station to journalists, arguing that Newsmax was on its way to profitability.

“We’re here to stay,” Ruddy crowed to CNN. “The ratings are showing that.” And: “We’ll probably overtake [Fox News] in the next six months in total audience,” he boasted to Newsweek.

Riding high, Ruddy entered discussions with Donald Trump Jr. and his girlfriend, Kimberly Guilfoyle, a former Fox News personality, about selling them a stake or even the entirety of Newsmax, according to three people familiar with the negotiations. The duo were to be the face of an offer backed by money from other entities, these people said.

But ultimately, Newsmax’s ratings spike driven by false election fraud claims was short-lived — and created a much bigger problem.

In December, election technology companies Smartmatic and Dominion — which were both frequent targets of debunked claims of election fraud that found ample airtime on Newsmax — sent legal demand letters to Fox News, Newsmax and a smaller conservative television station known as One America News, warning them that they should retract their false coverage.

Newsmax issued a lengthy “clarification” that debunked its own reporting, noting that the company “would like to clarify its news coverage and note it has not reported as true certain claims” made about the two firms.

Newsmax anchors read lengthy statements on air, and the website printed the clarification statement in full — denying its previous fanciful claims about George Soros or Nancy Pelosi exerting control over the firms. Last week, Newsmax also apologized to a Dominion employee for alleging that he had rigged the company’s voting machines.

Yet Newsmax continued to book MyPillow CEO Mike Lindell, one of Trump’s most ardent fans and a stubborn adherent to baseless claims of election fraud. In one Lindell appearance, he immediately veered off topic to claim he possessed “100 percent proof” of “all the election fraud with these Dominion machines.” After Newsmax’s Bob Sellers tried and failed to interrupt Lindell to read the prescribed warning letter, the anchor walked off the set in frustration.

Eventually, talks with Trump Jr. and Guilfoyle cooled around the time of the attack on the Capitol. One person close to the conversation, though, said things fell apart for reasons more complicated than the Jan. 6 disaster. It didn’t help that Ruddy had publicly boasted about the company’s value amid its surging ratings.

And yet ultimately, those ratings never brought Newsmax closer to profitability. In 2020, its best year ever, the station posted $26.4 million in revenue vs. $27.9 million in operating expenses, according to Kagan Research, compared with the more than $1 billion that Fox News could claim in profits.

Sources within the company, though, insist that Newsmax’s TV division is doing far better than the analysts’ numbers suggest and has actually reached profitability — a claim that can be hard to assess since the company is privately owned.

Through Newsmax, Ruddy has already made a mark on the media and democracy. The scars of the attack on the Capitol are still fresh, and how quickly investors and advertisers forget Newsmax’s false coverage of the election remains to be seen. Ruddy is still cultivating close connections to Trumpworld. In March he hired Trump spokesman Jason Miller as a contributor, shortly after Newsmax landed an interview with Trump at the Conservative Political Action Conference negotiated by Miller.

But whatever happens to Newsmax, Ruddy continues to create new products to market to his audience. In October he filed a trademark application for a new slogan: “Real News for Real People.” In April, while Ruddy and Trump palled around at Mar-a-Lago, his company filed five other trademark applications:

“Real Sports for Real People”

“Real Cars for Real People”

“Real Furniture for Real People”

“Real Coffee for Real People”

“Real Burgers for Real People”

Who constitutes “real people” in the Newsmax universe is unclear — but Ruddy probably already has their email addresses.

Alice Crites contributed to this report.