Ruddy has been a ubiquitous presence in Trump’s sphere over the past several months, the “Zelig” of the administration, as the Atlantic’s Rosie Gray wrote. He converses regularly with Trump and White House officials, and says he has given the president advice on everything from health care to Chinese relations to fake news.
On more than one occasion this year he has stirred controversy by inserting himself into conflicts among Trump’s staff.
But what has really put Ruddy on the radar lately are his frequent media appearances, in which he is fond of telling reporters, candidly and on-the-record, what Trump is thinking — or rather, what he thinks Trump is thinking.
That was the case this week, when Ruddy made the explosive assertion on PBS “NewsHour” that Trump was pondering whether to fire Robert S. Mueller III, the former FBI director tapped by the Department of Justice to oversee the probe into Russia’s meddling in the 2016 U.S. presidential election.
“I think he’s considering perhaps terminating the special counsel,” Ruddy said Monday, adding that he believed the move would be a mistake. “I think he’s weighing that option.”
The remark made waves not only because Ruddy has become one of Trump’s most sought-after and loquacious confidants, but because he had visited the White House just an hour before heading to the PBS interview, leading some to speculate that he was testing the waters for Trump, as The Washington Post reported.
Though no one in the administration specifically disputed Ruddy’s claim, White House press secretary Sean Spicer responded that Ruddy had not met with Trump that day, saying he “speaks for himself.”
As Washington buzzed about whether Trump would indeed give Mueller the ax, Ruddy went on to give more interviews about the possibility of such a move. He also criticized the White House press office’s response, saying “it’s amateur hour over there.”
The dust-up was nothing out of the ordinary these days for Ruddy, who seems to have grown more bold about offering his perspective.
What sets Ruddy apart from other Trump allies is his dual role as a newsman and a close friend of the president. As the head of a prominent conservative news organization with a monthly audience in the millions, his takes on the West Wing carry more weight than they might otherwise. He is quoted almost weekly in The Washington Post, the New York Times and other outlets, and makes regular rounds on cable news.
Ruddy goes out of his way to say he speaks only for himself, even if his remarks come suspiciously soon after a meeting with the president or White House insiders.
“I’m a newsman, so I’m going to give my views,” Ruddy told The Post Wednesday. “I’ve never on a very confidential matter ever gone on a show and quoted the president on it. People sometimes make the false jump that ‘he met with the president, therefore he must be talking on his behalf.’ I’ve never spoken on his behalf.”
But it’s not always easy to tell why, or for whom, Ruddy so readily offers his insights.
“Perhaps Ruddy tries to have it both ways,” CNN senior media correspondent Brian Stelter wrote Tuesday. “He trades on his access to Trump but emphasizes that ‘I am not speaking for the president.’ ”
Ruddy, 52, grew up on Long Island, studied history at St. John’s University in New York, and received his master’s in public policy from the London School of Economics. His journalistic career kicked off in the early 1990s, when he made a name for himself covering the Clinton White House for the New York Post. His reporting and subsequent book about the suicide of Deputy White House Counsel Vincent Foster won him star status among conservative commentators.
He founded Newsmax in 1998, catering mostly to right-leaning baby boomers through the outlet’s website and newsletters that quickly gained scores of subscribers, as he told Bloomberg in a 2014 profile. He met Trump shortly after. Both lived part time in Palm Beach, Fla., and would bump into each other intermittently, Ruddy said. Their friendship grew in the mid-2000s after Ruddy joined Trump’s Mar-a-Lago resort.
Over the years, Trump and Ruddy would discuss their views on a range of issues and occasionally bounce ideas off one another. In the run-up to the 2012 election, Ruddy said, Trump expressed his frustration with Mitt Romney, the Republican nominee, and said he was mulling a run of his own. Ruddy encouraged him.
“I don’t think he had really figured out what his political approach was going to be,” said Ruddy, who identifies as a Reagan conservative but is not a registered Republican. “I would say, if you run you’ve got to officially announce, and if you do, I’ll donate to your campaign. That was the Rubicon for him, the announcement.”
Since its founding, Ruddy’s Newsmax empire has steadily expanded. By 2014, it ranked as the most trafficked conservative news site on the Internet, topping 11 million visitors per month, as Bloomberg reported at the time. That year, Newsmax opened a new headquarters in Boca Raton, right down the road from Trump. Ruddy, then on the verge of launching NewsmaxTV, told Bloomberg that he was making a play to upend the conservative media landscape by shaving off Fox News viewers.
By 2017, Breitbart News had surpassed Newsmax as the Web’s leading conservative site, with more than 17 million visitors in January to Newsmax’s 7 million, as The Post reported. On top of that, it was Stephen K. Bannon, a former Breitbart chairman, and other Breitbart staffers who won seats in Trump’s White House, not Ruddy.
But Ruddy and Newsmax’s loyalty to Trump seem to have paid off in different ways. Ruddy said he has maintained an open line with the president since Day One.
“He’ll reach out to me and I’ll reach out to him,” Ruddy said. “I’ve been doing Newsmax for years, and the president used us as one of his platforms to reach his base. I’m not interested in looking for a job from the president and I’m not looking for financial gain from the president.”
Republican operative and Trump ally Roger Stone echoed those remarks in the Atlantic earlier this year.
“Newsmax is one of the earliest promoters of Trump,” he said. “They were in fact promoting Trump for president in 2012. Ruddy has always been a Trump promoter when others were not yet taking his candidacy seriously or his potential candidacy seriously.”
The squabble over the possible termination of the special counsel was not the first time Ruddy’s comments to the media have caused rumblings in Trump’s White House.
In February, Ruddy set off a media storm when he told reporters at Mar-a-Lago that Reince Priebus, Trump’s chief of staff, was “in way over his head.” He made the statements shortly after meeting with Trump for drinks, prompting questions about whether Trump was threatening Priebus through Ruddy. But Ruddy said later that he was only giving his opinion. A meeting with Trump, Ruddy and Priebus followed, and they appeared to smooth things over.
Another major reveal came in March, shortly after Trump baselessly accused President Barack Obama of wiretapping him. That weekend, Ruddy spoke with Trump twice and described the conversation in a column for Newsmax. He wrote:
I haven’t seen him this p‑‑‑ed off in a long time. When I mentioned Obama “denials” about the wiretaps, he shot back: “This will be investigated, it will all come out. I will be proven right.”
Trump has not publicly bristled at any of Ruddy’s commentary, even if it causes trouble for those around him. Ruddy said that may be because he always tries to be forthcoming with the president. If anything, he said, Trump seems to welcome his outspokenness.
“People who know us tell me that they think that because I’m honest with him in my assessments,” Ruddy said. “I think at the end of the day he respects it and values it.”
“We’ve had many frank discussions where we disagreed,” he added, “and it hasn’t changed the nature of our relationship one iota.”