The Trump Campaign Just Hired a Notorious Clinton Antagonist

Trump’s new deputy campaign manager has been trying to destroy Hillary Clinton for three decades.

Donald Trump with his new deputy campaign manager, David Bossie, at last year's Freedom Summit in Greenville, South Carolina. AP Photo/Rainier Ehrhardt


David Bossie has devoted his career to bringing down the Clintons—and Donald Trump just hired him to help run his campaign.

There’s no one in Washington (and perhaps the world) with a more encyclopedic knowledge of every Clinton scandal and conspiracy theory. Bossie, who will serve as Trump’s deputy campaign manager, first made a name for himself during Bill Clinton’s presidency, when he served as the chief investigator for the House committee that probed the Whitewater scandal and numerous other alleged Clinton misdeeds. Bossie was eventually fired from the committee for his overzealousness, and he went on to run a conservative nonprofit group called Citizens United, where he continued to amass an enormous opposition research file on the Clintons. Now Trump has finally given him a platform to launch his assault.

Bossie got his start working for the master of political dark arts, Floyd Brown, a political operative famous for creating the racially charged Willie Horton ad that helped obliterate the presidential hopes of Michael Dukakis in 1988. According to CBS, during the 1992 presidential campaign, Brown was running an independent political committee supporting George H.W. Bush. That year, he sent the young Bossie to investigate rumors about one of Bill Clinton’s alleged mistresses, who supposedly committed suicide in the 1970s after an affair with Clinton left her pregnant. Bossie allegedly tailed the woman’s mother and followed her to an Army hospital where her husband was recovering from a stroke. CBS reported that Bossie “burst into the sick man’s room and began questioning the shaken mother about her daughter’s suicide.”

Such tactics didn’t earn Bossie any fans in the Bush campaign, which filed a complaint against Brown’s operation with the Federal Elections Commission. But Bossie’s no-holds-barred methods were embraced by the Republican members of the Newt Gingrich-era House of Representatives, who were gung ho to investigate the Clintons. Bossie was hired as an investigator by Rep. Dan Burton (R-Ind.), the chairman of the House Government Oversight and Reform Committee. Burton and his committee spent years launching quixotic probes targeting the Clintons, at one point even investigating the conspiracy theory that deputy White House counsel Vince Foster had been murdered by the Clintons.

Bossie was eventually fired from the committee for releasing selectively edited jailhouse phone recordings of former US associate attorney general Webster Hubbell, who had worked with Hillary Clinton at the Rose Law Firm in Little Rock, Arkansas, and been sent to prison for tax fraud related to his work there. But Bossie continued to investigate the Clintons from his new perch at Citizens United, which Brown founded in 1988. In 2008, during Hillary Clinton’s first presidential run, Bossie plowed his years of oppo digging into a film attacking her. That film ultimately led to the Supreme Court decision Citizens United v. FEC, in which the court eliminated restrictions on corporate money flowing into the political system.

In the ensuing controversy over the Supreme Court decision and its effect on campaign finance, the film that spawned the ruling has been largely overlooked, but it’s a useful window into the type of mudslinging that Bossie can do for the Trump campaign. Hillary: The Movie was a political hit piece, rife with the wacky and paranoid conspiracy theories that have long characterized Bossie’s work. (At one point, the film suggests that the Clintons whacked the cat of one of Bill’s alleged former mistresses.) But it also features several forgotten Clinton scandals that should probably be given a second look now that Hillary is running for president.

I saw the film at its Georgetown premier in 2008, at an event headlined by Bossie himself. Here’s what I wrote afterward:

Hillary makes great use of the video footage from the 2000 “Hollywood Farewell Gala Salute to William Jefferson Clinton.” The star-studded event was organized and paid for by Peter F. Paul, a repeat felon and con artist who had cozied up to the Clintons in the waning days of the administration. Aiding him was Aaron Tonken, another con man who was later convicted of defrauding charities, who helpfully provides an interview for the film from prison.

Paul, who is interviewed extensively in the movie, paid $1.2 million to put on the gala, which raised money for Hillary Clinton’s Senate race. Her Senate campaign, however, reported to the Federal Election Commission that the event only cost $523,000. (In-kind donations such as hosting a party count toward candidate spending limits.) The FEC eventually fined Clinton’s campaign $35,000 for underreporting the cost of the party. Hillary Clinton’s finance director was tried and acquitted for his role in reporting the event cost.

After the Washington Post reported on Paul’s criminal history, which included drug charges and all sorts of financial shenanigans (even defrauding Cuba, if you can imagine the level of criminal ingenuity that would entail), Hillary Clinton distanced herself from him. But Hillary showcases lots of footage and chummy photos of the former first lady with Paul, even a video of a conference call she made to him. All this suggests a close relationship that’s going to be tough to avoid addressing if she ends up facing off with a Republican next fall.

The criminal past that makes Paul a problem for Clinton also makes him a problem for the filmmakers. To address this issue, Citizens United hired a professional polygrapher to administer a lie-detector test to Paul on film, which of course he passes. It’s a laughable scene, and it’s tempting to dismiss the guy’s story, except that a lot of it is true. The Clintons have still never explained how they hooked up with Paul. As Paul points out in the film, his house was prepared for presidential visits, and he also visited the White House on several occasions, so it’s hard to believe that the Clintons didn’t know he was a crook long before the gala. You don’t need to be James Carville to see how the episode may play out in campaign ads next summer.

Those ads never got made because Hillary Clinton lost the Democratic primary to Barack Obama. This cycle, Bossie has been running the Defeat Crooked Hillary Super PAC, where he has attacked Clinton from the sidelines. But with his elevation to the Trump campaign, he can deploy his treasure trove of Clinton dirt directly. Whether Bossie can behave himself and avoid becoming part of the story remains to be seen. Trump often says he hires only the best people—and in this case, it’s true. As a political hit man, Bossie is the best there is.