Bossie stands in a long and dubious tradition of political attack hacks whose hyperaggressive tactics frequently lead them to step over the line of fair play. On the media side, the granddaddy of the GOP hit men, credited with creating the modern attack ad, is Alex Castellanos, who is now producing commercials for the Bush-Cheney campaign. In 2000, for instance, Castellanos embarrassed the Bush campaign when someone discovered that an attack ad he had produced flashed the word "rats" on the screen for a split second. Castellanos denied using subliminal advertising, but put on the defensive, Bush had to yank the spot.

Bossie has engaged in such questionable or downright slimy tactics on many occasions. Here are some of his more famous misses:

  • During the 1992 presidential campaign, Bossie got into a fistfight with a Little Rock, Ark., private investigator, Larry Case, who said he had damaging information on Clinton. Bossie told police that Case had punched him after Bossie refused to pay Case a $10,000 advance as they were preparing to board a flight at Little Rock National Airport.
  • That same year, Bossie set out to prove that a young pregnant woman named Susan Coleman had committed suicide in 1977 after having an affair with Clinton. Coleman's mother told CBS that Bossie hounded her relentlessly with his false story, even following her to an Army hospital in Georgia, where she was visiting her husband, in recovery from a stroke. Bossie and another man "burst into the sick man's room and began questioning the shaken mother about her daughter's suicide," CBS reported.
  • Also in 1992, President George H.W. Bush, repudiating Bossie's tactics, filed an FEC complaint against Bossie's group after it produced a TV ad inviting voters to call a hot line to hear (almost certainly doctored) tape-recorded conversations between Clinton and Gennifer Flowers.
  • In 1994, Bossie traveled to Fayetteville, Ark., with an NBC producer, where the two allegedly "stalked" and "ambushed" Beverly Bassett Schaffer, a former state regulatory officer and a lawyer who had played a small role in the so-called Whitewater conspiracy. The two confronted Schaffer outside her office and, after she refused an on-camera interview, reportedly chased her across town, until she found refuge in the lobby of an office building.
  • In February 1996, Citizens United mailed out a fundraising letter bragging that it had "dispatched its top investigator, David Bossie, to Capitol Hill to assist Senator Lauch Faircloth in the official US Senate hearings on Whitewater." Another mailing reported that Bossie was "on the inside directing the probe." Democrats subsequently cried foul that a federal employee was actively raising money for a partisan group, so D'Amato forced Bossie to submit an affidavit proclaiming his independence from Citizens United.
  • In November 1996, Bossie improperly leaked the confidential phone logs of former Commerce Department official John Huang to the press. And he did that by deceiving other GOP congressional aides, according to an account published in Roll Call, which quoted one Republican aide comparing Bossie's deceptive presence to "Ollie North running around the House."
  • In July 1997, James Rowley III, the chief counsel to the House Government Reform Committee, which was investigating allegations of campaign finance wrongdoing by the Clinton administration, resigned his position after committee chairman Burton refused to fire Bossie. In his one-page resignation letter, Rowley, a former federal prosecutor employed by Republicans, accused Bossie of "unrelenting" self-promotion in the press, which made it impossible "to implement the standards of professional conduct I have been accustomed to at the United States Attorney's Office." (Bossie's habit of self-promotion paid off; during one four-week stretch in early 1994, Bossie and Brown were profiled by the Chicago Tribune, the New York Times and the Washington Post, each marveling at the power the activists were wielding.)
  • The breaking point came in May 1998, when Bossie, then 32, oversaw the release of the doctored Hubbell tapes. As Roll Call reported at the time, "At Bossie's request, Burton sat on the tapes for nearly a year until word started to leak that Hubbell might be indicted by [Kenneth] Starr for tax evasion. Bossie, who supervised the tapes along with investigator Barbara Comstock, oversaw the editing of Hubbell's prison conversation[s] and decided to release them the day before Hubbell was indicted." According to Roll Call, Bossie enjoyed unusually close working relations with Starr investigators.

    The tapes were edited for "privacy" considerations, according to Bossie. But they were also edited to completely omit key exculpatory passages, including one in which Hubbell exonerated Hillary Clinton of wrongdoing. Gingrich ordered a reluctant Burton to fire Bossie.

    Yet, in 1999, Bossie was given the Ronald Reagan Award by the Conservative Political Action Conference for his "outstanding achievements and selfless contributions to the conservative movement." And it wasn't just the conservative base that continued to embrace Bossie after the Hubbell tape disgrace; so did many in the Washington press corps.

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