WASHINGTON — Relationships have always been President Donald Trump’s currency and comfort, helping him talk his way into real estate deals over three decades in New York. Those who know him best say that his outer confidence has always belied an inner uncertainty, and that he needs to test ideas with a wide range of people.
As Trump’s White House advisers jostle for position, the president has turned to another group of advisers — from family, real estate, media, finance and politics, and all outside the White House gates — many of whom he consults at least once a week.
Media mogul Rupert Murdoch is on the phone every week, encouraging Trump when he’s low and arguing that he should focus on the economy rather than detouring to other issues. Developer Richard LeFrak is a soothing voice who listens to Trump’s complaints that cost estimates for the border wall with Mexico are too high. Sean Hannity tells the president that keeping promises on core Republican issues is crucial.
Trump’s West Wing aides, like President Bill Clinton’s staff two decades before, say they sometimes cringe at the input from people they can’t control, with consequences they can’t predict. Knowing these advisers — who are mostly white, male and older — is a key to figuring out the words coming from Trump’s mouth and his Twitter feed.
Here, based on interviews with more than a dozen friends, top aides and advisers inside and outside the White House, are 20 of Trump’s outside touchstones.
Trump’s relationships depend on two crucial measures: Personal success and loyalty to him. Murdoch excels in both categories. His New York Post vaulted Trump from local housing developer to gossip-page royalty, and his Fox News Channel was pro-Trump in the 2016 general election.
The two share preferences for transactional tabloid journalism and never giving in to critics. (Trump said fallen Fox star Bill O’Reilly should not have settled sexual harassment complaints.) The president’s relationship with Murdoch is deeper and more enduring than most in his life, and in their calls they commiserate and plot strategy, according to people close to both.
Murdoch even called the White House press secretary, Sean Spicer, to buck him up after Spicer was savaged for a remark about Adolf Hitler.
Presidents always deploy surrogates to appear on television to spout their talking points, but Trump has expanded on that by developing relationships with sympathetic media figures like Hannity who also serve as advisers. Hannity, the Fox News host, defends Trump’s most controversial behavior in public, but privately, according to people close to Trump, he urges the president not to get distracted, and advises him to focus on keeping pledges such as repealing the Affordable Care Act.
The chief executive of Newsmax Media is a longtime Mar-a-Lago member and was a Trump cheerleader among conservative media well before the website Breitbart joined the parade. He employs writers and editors who tracked Trump’s career when they were at The New York Post. He recently visited the Oval Office, and he and Trump kibitz in Florida and by phone.
Dillon seemed out of place when she spoke at a too-large lectern in the lobby of Trump Tower on Jan. 11, describing the steps Trump planned to take to separate himself from his business. But Dillon, an ethics lawyer who worked out a highly criticized plan for Trump to retain ownership of his company but step back from running it, has repeatedly counseled the president about the business and made at least one White House visit. (Michael Cohen, a veteran Trump aide, has been serving as his personal lawyer.)
Despite his “you’re fired” slogan, the president dislikes dismissing people. Lewandowski, Trump’s hot-tempered first campaign manager, was fired last June but never really went away. A New England-bred operative whose working-class roots and clenched-teeth loyalty earned him Trump’s trust, he continued to be in frequent phone contact with Trump until the election and beyond. Friends of Lewandowski say that he can see the windows of the White House residence from his lobbying office on Pennsylvania Avenue, and that the view is even better during his visits to the West Wing, including when the New England Patriots were at the White House this past week.
The former House speaker talks more with Trump’s top advisers than he does with the president, but his presence permeates the administration. Gingrich’s former spokesman is at the State Department, and two former advisers work in the West Wing. Gingrich has relentlessly promoted Trump’s policy adviser, Stephen Miller, as the West Wing conservative ballast as the chief strategist, Stephen Bannon, has been under fire.
Their fathers were developers together in New York, and the two men have been friends for decades. LeFrak is a Mar-a-Lago member, and he agreed to be part of an infrastructure effort that Trump hopes to put forward. Trump has turned to him to vent frustrations about the slow pace of bureaucracy.
Trump divides the people around him into broad categories: family, paid staff and wealthy men like Barrack whom he considers peers. A sunny and loyal near-billionaire who has socialized with the president for years, Barrack is less a strategic adviser than a trusted moneyman, fixer and sounding board who often punctuated his emails to Trump with exhortations like “YOU ROCK!” He has urged Trump to avoid needless, distracting fights.
Under Barrack’s leadership, Trump’s inaugural committee raised a record $106.7 million, much of it from big corporations, banks and Republican megadonors like Las Vegas billionaire Sheldon Adelson. Barrack also helped usher Paul Manafort, the international political operative under scrutiny for his ties to Russia, into the Trump fold last year. The velvet-voiced Barrack does not seek out attention for himself, one of the most important and elusive qualities by which the president judges people.
The chairman and chief executive of the Blackstone Group, Schwarzman is the head of Trump’s economic advisory council. He and the president don’t speak daily, West Wing aides said, but do talk frequently. Schwarzman has counseled him on a number of topics, including advising him to leave in place President Barack Obama’s executive order shielding young undocumented immigrants, known as “Dreamers,” from deportation.
A good way to get on Trump’s side is to do a deal with him, particularly if it means rescuing him from his own financial crisis. That’s what real estate tycoon Steve Roth did a decade ago when he bought out Trump’s share in a New York City real estate deal that went sour. Roth, head of Vornado Realty Trust and a longtime Democratic donor, also helped Trump’s son-in-law, Jared Kushner, when he injected $80 million into 666 Fifth Ave., a Kushner family property in danger of defaulting on $1.1 billion in loans. Trump speaks with Roth frequently, and is leaning on him to help develop a trillion-dollar infrastructure package expected this year.
Trump has 20-odd business partners, but none is closer to him than Ruffin, 82, a Texas billionaire who has lent his ear and private jet. The president was best man at the 2008 wedding of Ruffin to his third wife, a 26-year-old model and former Miss Ukraine. Ruffin has a knack for showing up when Trump needs him most and remains a die-hard defender. “This stuff about him having financial investments all over Russia — that’s just pure crap,” Ruffin told Forbes. “I went to Russia with him. We took my airplane. We were having lunch with one of the oligarchs there. No business was discussed.”
Rounding out Trump’s roster of wealthy octogenarians is this 81-year-old corporate raider and real estate mogul who occupies perhaps the most respected perch in the president’s circle of businessmen buddies. The affection is long-standing: The New York-bred Icahn has known Trump and his family for decades. It’s also numerical: Icahn is worth an estimated $16 billion, a major plus in the eyes of a president who keeps score. Icahn serves as a free-roving economic counselor and head of Trump’s effort to reduce government regulations on business.
Man of Mystery
Few alliances in politics are as complicated as the 40-year relationship between the Nixon-tattooed Stone and Trump. Stone won’t say how frequently they speak these days, but he shares the president’s tear-down-the-system impulses and is ubiquitous on cable, on radio and on the website InfoWarsnews defending Trump.
Perlmutter, the chief executive of Marvel Comics who is so reclusive that few public photographs exist of him, has been informally advising Trump on veterans issues. The two men are old friends, and Perlmutter has been a presence at Mar-a-Lago club.
The owner of the Patriots is a Democrat but his loyalty to Trump, Kraft once said, dates partly to the president’s thoughtfulness when Kraft’s wife died. Trump loved talking about the Patriots during the campaign, and Kraft has been a Mar-a-Lago presence since the transition.
The First Lady
Melania Trump is uninterested in the limelight, but she has remained a powerful adviser by telephone from New York. Among her roles: giving the president feedback on media coverage, counseling him on staff choices and urging him, repeatedly, to tone down his Twitter feed. Lately, he has listened closely and has a more disciplined Twitter finger.
Kushner, the president’s son-in-law and palace gatekeeper, has shown a capacity to hobble his rivals, but few have been finished off. The most durable has been Christie, whose transition planning, several West Wing aides now concede, should not have been discarded. He has been a frequent Oval Office visitor and has worked with the White House on the opioid addiction crisis.
Trump and the clean-cut and wonky Wisconsinite aren’t exactly best friends forever. But their relationship is closer than in the bad old days of the 2016 campaign when Ryan delayed a hold-my-nose endorsement of Trump, whose morality he had long questioned. But as the president’s agenda passes through the razor-blade gantlet of the House, where Ryan faces the constant threat of opposition and overthrow, the two men have become foxhole buddies.
The two sons and the president insist they no longer discuss company business. But the family is close and Trump still speaks to his sons frequently, inquiring about their lives and searching for gut-checks on his own.