Loser Express

David Bossie: The Man the Trump Train Left Behind

It seems like everyone on Trump’s senior campaign team was rewarded after his victory. Everyone, except Deputy Campaign Manager David Bossie.

Photo Illustration by Elizabeth Brockway/The Daily Beast

Late last month, Fox News Channel announced that it had signed David Bossie, the Citizens United president and Donald Trump’s former deputy campaign manager, as a contributor for political analysis on Fox News and Fox Business. It’s not a bad gig—but it doesn’t quite match the high-profile or gravitas he may have thought he had coming as a part of the campaign’s senior team.

Bossie, a longtime conservative activist and operative, had his post-election designs on a higher position of power in the Trump era he helped forge, say multiple people close to Bossie and Team Trump.

After all, Stephen Bannon, who served as CEO of the Trump presidential campaign, is now the White House chief strategist (and one of the most powerful people on the planet). Kellyanne Conway, former Trump campaign manager, ended up with her title of counselor to the president. Hope Hicks, The Donald’s “accidental press secretary” for the campaign and then presidential transition, works in the Trump White House as a strategic-communications director. Former top aide Jason Miller was off to help lead the White House comms shop, until an affair was alleged by a former Trump adviser. Even Omarosa, the president’s former reality-TV co-star and the campaign’s black-outreach czar, is now working in the West Wing.

So, what the hell happened to Bossie, who Trump-campaign insiders credit as another major player in Trump’s upset victory?

“David was more of a ‘campaign manager’ than Kellyanne ever was,” one senior member of the Trump campaign, who requested anonymity to speak candidly, told The Daily Beast. “A more accurate description for Kellyanne would have been ‘spokeswoman’ and then ‘adviser.’”

Conway, for her part, will say that she has nothing but fond memories of “Dave” from the trail.

“Dave is a friend and colleague of decades, and was a key member of our senior team on the campaign,” she emailed The Daily Beast. “His mastery of grassroots engagement and pockets of voter possibility on the electoral map informed decisions on resource deployment, and scheduling rallies and other major touch-the-voter events for our now President and Vice President. Dave worked tirelessly, separated from his family, and fully committed to the election of Trump-Pence. He traveled, jousted on TV, and interfaces with our team on the ground.”

After Trump tapped Bossie for deputy campaign manager late last year, Trump himself called the Citizens United president “a friend of mine for many years,” in an interview with The Washington Post. “Solid. Smart. Loves politics, knows how to win,” Trump added. Bossie would later join Trump’s presidential transition team on the leadership staff as deputy executive director.

“He deserved better than this—he deserves more for what he did,” the Trump campaign source said.

On stage at the 2017 Conservative Political Action Conference late last month, Bossie waxed nostalgic about the election past during his speaking slot on the last day of the event (not exactly prime time).

“2016 was a historic year, and I’m truly honored to have been part of it,” Bossie said, while discussing the “Trump phenomenon” of the past election. “I got a chance to serve as the deputy campaign manager for Mr. Trump, and then I got a chance to serve as the deputy director of the presidential transition team. And those were high honors for me, and my career, and my life. It was a wonderful five months to be able to work on it.”

Prior to hopping aboard the Trump train, Bossie ran the “Defeat Crooked Hillary” super PAC. Ten days after Trump was inauguration, Bossie and several other former Trump aides launched the pro-Trump nonprofit “America First Policies”—a group that so far appears to be in complete functional disarray.

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Bossie did not respond to The Daily Beast’s requests for comment on this story. But former Trumpland colleagues paint a picture of Bossie as a longtime pal of Trump’s, and someone charged with coordinating the “nuts and bolts” of campaign operations, particularly in the homestretch of the fight against Democratic presidential nominee Hillary Clinton. He was also instrumental in the strategy in the final month of the presidential race to focus on Bill Clinton’s alleged sexual violence against women, in an attempt to counter Trump’s long list of accusers.

“He was largely responsible for the decision to move components and campaign resources to Michigan and Wisconsin at the last minute, and moved the president’s schedule,” a senior Trump campaign aide told The Daily Beast. “Kellyanne would do these things with the pollsters, then Bossie came up with the plan of how to get them there… and worked closely with the digital team, finance department, and [communications] team to do it. He tied [it all] together.”

Another Team Trump alumnus described Bossie as a “key component” to why “Trump went [to ‘Blue Wall’ states], and why he won” the White House.

Sources close to Bossie describe his ambition to become, if not a player directly inside the West Wing, the next chairman of the Republican National Committee, after former chair Reince Priebus headed to the Trump White House.

In mid-November, Politico reported that Bossie had made it to the shortlist for Priebus’s successor. Ultimately, Bossie did not make it far in the post-election RNC sweepstakes because party “leaders had been wary from the get-go about his combative, brash style, anyway,” one RNC source said.

“He had the trust of the president, so he seemed like a natural [fit],” a former Trump campaign adviser said. “But the RNC made its decision.”

The main reason, according to sources with knowledge of the process, Bossie wasn’t destined to head the RNC was he butted heads with the wrong party bigwigs. In December, The New York Times reported that Bossie “frequently clashed with Mr. Priebus,” and that Trump was apparently “dissatisfied with [Bossie] by the end of the campaign.”

It is less clear exactly what kept Bossie out of the West Wing. But according to two sources close to both Bossie and Trump, the new president has still kept in touch with his former deputy campaign manager. “He still communicates with the president [via phone] to discuss what can be done on the outside,” a GOP political operative with knowledge of their recent conversations said. “They’ve discussed traditional media and conservative media and how to get the president’s message and agenda out on those platforms.”

The White House did not respond to requests for comment on this characterization of the ongoing relationship.

“It makes total sense why he’s now on Fox News,” one Trump campaign aide said.

On the campaign trail, Trump and Bossie would often discuss best practices for disseminating the Republican presidential nominee’s message and right-wing nationalist-populist vision on conservative and mainstream media, according to veterans of Trump’s campaign.

Trump has long been obsessed with media coverage, and was himself once a part of the conservative-media apparatus, having landed a regular Fox News segment titled “Mondays With Trump” starting in early 2011. Prior to his Fox News contributorship, Bossie role in conservative media including collaborating on several film projects with Steve Bannon, his former Trump campaign colleague.

Bossie and Bannon go way back. It was Bossie who was responsible for introducing Trump to Bannon in 2011, and Bossie had written columns for Bannon’s website Breitbart as recently as late May 2016.

In fact, Bannon’s old writing partner in Hollywood blames in part blames the Citizens United president for the Steve Bannon who the world knows today.

“[Steve] changed considerably—noticeably,” Julia Jones, Bannon’s former Hollywood screenwriting partner, told The Daily Beast last week. “A major change seemed to happen when he started working with Bossie [in the late aughts].”

Bannon had previously co-authored with Jones more lighthearted fare, such as a Shakespearean hip-hop musical about the Los Angeles riots, which the two had tried to stage together in 2006. And then, according to Jones, Bossie entered the picture.

“Steve became less playful, less creative, darker, and more negative in what [movies and projects] he wanted to work on—more of a sense of doom and ‘end of the world’ feel started to really creep in right after he started [collaborating] with him,” she recalled.

“There’s always been a part of me that has blamed Bossie for what Steve has become,” Jones continued. Jones, an avowed liberal, was Bannon’s writing partner and close friend for nearly two decades. Late last year, the two of them had a falling out over his role in Trump’s rise, during which Jones had grown “so disgusted” at what her longtime friend had done.

Jones had already disliked Bossie by reputation, having read about the man’s anti-Clinton tactics in the ’90s and his involvement with Citizens United (and the group’s landmark Supreme Court case). In the late aughts, when Bossie and Bannon began collaborating more on movie projects, Jones says that she had to tell Bannon, “I can’t work with him, I’m sorry.”

Bannon, as Jones remembers it, replied, “Fine,” then continued to work with Bossie regardless.

“From Day 1 I knew [Bossie] was bad news—I didn’t want anything to do with him,” she said.

Bannon did not respond to a request for comment regarding his relationship with Bossie, or their influence on each other.

A couple decades later, Jones and Bannon’s relationship, both personal and professional, has bitten the dust. In the meantime, the Bossie and Bannon pairing helped pave the way for a Donald Trump presidency.

And now with Bossie on the outside of the Trump White House looking in, he might be relegated to navigating the new political reality of Trumpism without the luxury of a new seat of power for himself.

For instance, his position at America First Policies may have died before it really even started. According to two sources with knowledge of the nonprofit’s early inner turmoil, Bossie isn’t actively working with the group he supposedly helped launch.

One source said Bossie “bolted” after “he and Rebekah [Mercer] didn’t like what they saw.”

Katrina Pierson, a former Trump campaign national spokeswoman and one of America First Policies’ principals, did not respond to a request for comment on Bossie’s involvement.

“I think Bossie has walked,” another source said.

with additional reporting by Gideon Resnick