With his decades-long fixation on Bill and Hillary, Bossie is not simply an obvious choice to aid Team Trump in its slash-and-burn mission to either defeat or, barring that, delegitimize Hillary. The 50-year-old crusader is, in many ways, an embodiment of the toxic, obsessive, vendetta-driven political spirit that animates Trumpworld.

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Bossie came to national notice alongside his nemeses. During the 1992 election, the young conservative was dispatched to sniff around Bill Clinton’s sex life by the Republican operative Floyd Brown, the founder of Citizens United and father of such brass-knuckle political hits as the infamous Willie Horton ad. Bossie tackled the job with such zeal that he got called out on CBS Evening News for his rough handling of one woman’s family. The Washington Post recalled the segment in a 1997 profile:

Correspondent Eric Engberg reported that Bossie and a retired D.C. police officer, Jim Murphy, both working for Brown, had been harassing the friends and family of Susan Coleman, who had committed suicide years before. They were trying to confirm that Coleman shot herself "following a love affair with her law professor, Bill Clinton, that left her pregnant," Engberg reported. Bossie and Murphy trailed Coleman's mother to an Army hospital in Augusta, Ga., where her husband was being treated for a stroke. "Here the two men burst into the sick man's room," Engberg narrated, "and began questioning the shaken mother about her daughter's suicide.” A chastened Bossie later told friends that the CBS story had made his grandmother cry.

After Clinton’s election, Bossie turned his attentions to ginning up the Whitewater scandal, feeding info to reporters and Republican Congress members alike. In 1995, he joined the staff of Senator Lauch Faircloth, a member of the Whitewater Committee. His reputation as a pitbull grew—as did the sense that he had it in for the Clintons. The Post profile quoted an anonymous GOP congressional staffer, who explained, “He’s a decent guy, he’s savvy, he generally knows how to deal with the press, he knows how to advance a story … But the problem is, he leads with his agenda, and that drives everything—and that just tends to undermine the credibility of the investigation.”

When House Republicans launched a probe into the 1996 Clinton campaign’s fundraising practices, Bossie wound up as the chief investigator for the member in charge, Dan Burton. Eighteen months into the job, Bossie was forced to resign for questionable tactics. (Specifically, he distributed selectively edited transcripts of investigators’ jailhouse conversations with the Clinton crony Webb Hubbell.) The New York Times reported that then-Speaker Newt Gingrich himself had pressed for Bossie’s ouster because the investigator had “become an embarrassment to the Republicans.”