As Donald Trump prepares to pick his third White House chief of staff in two years, aides and advisers say he is torn between two competing impulses. He understands that the right person for the role is someone who will be subservient to his management style and execute his vision. But his love for the glitzy hire has drawn him towards tapping a big name and alpha personality that he may clash with once again.
The competing interests were supposed to have been a non-issue with the likely ascension of Vice President Mike Pence’s chief of staff Nick Ayers— a young but seasoned and, most importantly, behind-the-scenes political animal—to replace the departing John Kelly.
But Ayers turned down the role, and now the president and his aides are frantically searching for a candidate who can match Trump’s difficult, often contrasting demands. On Sunday, the president tweeted that he was still “in the process of interviewing some really great people for the position of White House Chief of Staff,” and chided members of the media for portraying Ayers as a lock. One current White House official compared it to tripping and then telling onlookers that you had meant to lose your footing.
One indication that Team Trump is now starting from scratch—and searching for a chief of staff who can both serve the president’s needs and be portrayed as a high-profile hire—is the emergence of David Bossie on the shortlist, alongside former New Jersey Gov. Chris Christie, Rep. Mark Meadows (R-NC), and White House budget director Mick Mulvaney.
Meadows, so far, is the only person listed who has publicly expressed interest in the job, telling The Daily Beast on Monday that he would “consider” accepting an offer to be chief of staff “if it’s right for my district and if it’s right for the country.”
“It’s not something I’ve been campaigning for. It’s not something that was really even on the radar until my phone blew up yesterday when Nick Ayers didn’t take the job,” Meadows joked.
But it’s Bossie, the president of conservative nonprofit Citizens United, whose name has raised many eyebrows.
His inclusion on the shortlist would have seemed remarkable just two years ago. But aides who have served under both Kelly and former White House chief of staff Reince Priebus, say Bossie has the characteristics that could allow him to succeed where they failed. He is comfortable working away from the spotlight and executing the president’s mission. He also knows Trump—having been a top deputy on the 2016 campaign—and spent years as a top House investigator during Bill Clinton’s presidency, giving him knowledge of the congressional oversight process the president is about to be subjected to.
And yet, sources also say Bossie is unlikely to get the job, not least because of tensions with members of the Trump family that began during the 2016 campaign and linger to this day.
“I just don’t see Jared and Ivanka allowing Bossie to come in,” a source familiar with the hunt said. “They’re the ones who stopped him [from getting a White House post] last time. Bossie did some things on the campaign that rubbed Jared the wrong way.” Asked what those things were, the source would only say, without elaboration, “classic Bossie shit.”
Bossie did not respond to a request for comment on this story. Neither did the White House press office.
Bossie also has the problem of being very close with one-time Trump campaign manager Corey Lewandowski—the two are out with their second co-authored book—who one former top White House official said is considered “toxic” within the administration.
Aides say they suspect that Lewandowski is trying to work Trump privately on who to pick as his next chief of staff. He’s making a public push as well, telling Fox News host Brian Kilmeade on Monday morning that Trump should not “just go to another process individual” like Kelly. “It’s not about the process, it’s about understanding what the Democrats are going to do.”
The next chief of staff, Lewandowski said, must recognize and prepare for the “subpoena cannon that is about to be aimed at the White House.”
A former White House official, who spoke on condition of anonymity, echoed Lewandowski’s characterization, and suggested that it was a de facto endorsement of Bossie.
“[Bossie’s] time as chief investigator for Clinton makes him very well suited to handle the Trump investigation,” the source said.
Jack Kingston, a former Republican member of Congress and a current Trump media surrogate, said he felt that Bossie would meet the three criteria Trump needs to be an effective chief of staff: someone familiar with how politics works on the federal level, someone with experience in congressional investigations, and someone with a backbone to say “no” to the president.
“You need someone who is not afraid of losing the job,” said Kingston. “You have to respect the hell out of the president but you can’t be so afraid of losing the job that you can’t say no.”
But while a willingness to stand one’s ground may be considered a useful characteristic for a chief of staff in past administrations, it doesn’t necessarily endear oneself to the current president.
Three sources familiar with Bossie and Trump’s relationship tell The Daily Beast that, toward the end of the 2016 campaign and during the Trump presidential transition, Bossie had worn out the future president’s patience by being too assertive in his attempts at constructive criticism. Two sources recall Bossie getting in trouble with Trump for merely saying what other senior campaign aides were thinking, including by directly advising Trump to act more “presidential” and to tone down his frenetic Twitter habits (Indeed, Trump’s own tweets would end up getting cited in court against him and his administration.)
This would annoy Trump, to the point that by the time the transition came, the president-elect had decided that Bossie would not serve in his West Wing, and instead remain a key outside ally. Bossie, for his part, kept loyal to Trump over the past two years, and, in return, has managed to get back more fully in the president’s good graces—as a phone buddy, a political adviser, and as a welcome guest at the Trump White House.
“The one thing about Dave Bossie is that he does know the president and he does know the political side of it,” said Kingston. “He’s been around.”
—With additional reporting by Andrew Desiderio