So it wasn't entirely surprising in September when Trump, whose campaign from the get-go engaged in conspiracy theories and rumor-mongering, hired one of the most notorious anti-Clinton conspiracy theorists and rumor-mongers as the nominee went into the general election homestretch. But now Trump is facing numerous allegations claiming similar behavior -- or worse -- that the operative tried to peddle against the former President, in a scandal that is exacerbated by the dredging up of a 2005 tape where Trump boasted about predatory behavior.
It's just the kind of controversy that Bossie has spent decades trying, and mostly failing, to spin around the Clintons.
Around the time Bill Clinton began making his ascent up the national political ladder, Bossie committed his career to digging up salacious dirt on the promising politician.
He teamed up with GOP operative Floyd Brown -- famous for 1988's "Willie Horton" ad -- and the two eventually worked under the political oppo shop Citizens United. Later, Citizens United would become best known for its role in the landmark 2010 Supreme Court decision loosening campaign finance laws. What brought the group into the courtroom? An anti-Clinton documentary it produced targeting Hillary ahead of her 2008 presidential bid.
But before then, Bossie and the group had been engaged in all sorts of anti-Clinton pursuits.
A gripping CBS report in July 1992 detailed how Bossie – then working for Brown and his group, Presidential Victory Committee – was working to try to connect the suicide of a young woman, Susan Coleman, to Bill Clinton. The allegations had come from an anonymous letter that had been mailed to news organizations across the country and alleged that Coleman had been a student of Bill Clinton’s and had become pregnant with his child before committing suicide. News organizations concluded it was a “nasty hoax.”
Coleman’s family told CBS at the time that there was “no truth” the the letter.
But that didn’t stop Bossie from traveling South to collect information about Coleman’s family, former neighbors and friends. At one point, CBS reported that Bossie trailed Coleman’s mother “down country roads” and to a hospital “where her husband was being treated for a stroke.”
That is when CBS reported that Bossie and his co-investigator “burst” into the man’s hospital room and began asking Coleman’s mother questions about her daughter’s suicide.
In a recorded interview with Coleman’s sister, Brown told her that he had sent Bossie and his co-investigator down to try and prove how Bill Clinton was too morally corrupt to be president.
“I want to basically have my lawyers approach Clinton’s lawyers and tell him we want him out of the race because he is not morally qualified to be president," Brown said.
Bossie and Brown continued looking into Clinton's sex life, with their group Citizens United, as he got closer to the White House. It didn’t take long for their digging to make even Republicans uncomfortable. In 1992, President George H.W. Bush file a FEC complaint against the group after an anti-Clinton effort Bossie and Floyd spearheaded that included a phone line where callers could hear alleged sex tapes between Clinton and Gennifer Flowers. Bush described Citizens United’s tactics as "the kind of sleaze that diminishes the political process."
A few years later, however, Republicans were ready to exploit Bossie's approach and he was brought on as a chief investigator for the House Government Reform and Oversight Committee in 1996. Its chair, Rep. Dan Burton (R-IN), became the face of the House GOP's hounding of the Clintons over Whitewater, Vince Foster, and the various Clinton sex scandals. In the meantime, Bossie gained a reputation of his own.
"Not since Roy Cohn -- the bare-knuckled chief counsel for Sen. Joe McCarthy in the Red-hunting hearings of the 1950s -- has a congressional staffer been so thoroughly demonized by his enemies. And it has been a long time since a staffer stirred up such a fuss in Congress," the Washington Post wrote in a 1997 profile.
By the time the Monica Lewinsky scandal had reached its fever pitch, it became clear to some of Clintons' fiercest critics that Bossie had gotten over his skis in his peddling of dirt. House Speaker Newt Gingrich in 1998 fired Bossie from Burton’s committee. At the time, Burton made Bossie’s departure out to be a mutual decision between the congressman and the staffer, but Gingrich soon made clear Bossie was harming the House GOP’s cause.
What finally prompted GOP lawmakers to cut Bossie loose was his release of a doctored transcript related to the Whitewater scandal, but Gingrich reportedly labeled his whole operation a “circus.”
"The focus has got to be on the crimes that are being committed at the White House," Gingrich said in a closed-door meeting with Republicans, a lawmaker told the Washington Post. "I want you to forget the word 'scandals,' and start using the word 'crimes.'"
After the House GOP put him out to pasture, Bossie made himself no stranger to the media circuit. He defended his obsessive examination of Clinton’s extramarital sexual relationships by arguing that the details were necessary to prove that the president had committed perjury.
It should be noted that Trump's own very public denial of sexual misconduct prompted some of his accusers to go public with their sexual assault allegations against Trump, saying they were motivated to do so when Trump said during the second presidential debate that he had never engaged in the behavior he talked about on the 2005 hot mic tape.
Burton told TPM that there is nothing about Bossie's current role in the Trump campaign that he views as a paradox.
“He only did what I asked him to do,” Burton said. “I don’t see any irony at all. I support Donald Trump, too, so I guess you could say the same thing of me," Burton said.
In the late 1990s, during his first round of Clinton trashing, Bossie was particularly incensed when he and his fellow anti-Clinton crusaders become the subject of scrutiny, with reports that a book about them was on the way. Bossie said that the sex life of his former boss Burton -- whom, it had been revealed, fathered a child in an extramarital affair -- should remain off limits.
Liberal pundit Bill Press, on a 1998 episode of Crossfire, asked Bossie, “Republicans open an investigation into Bill Clinton's sex life, can't they expect the same thing into their life and isn't that fair?”
“If they lie about it, absolutely,” Bossie said.