Bossie was hired by the chairman of the House Committee on Government Reform and new Oversight in 1997 as chief investigator to look into possible campaign finance abuses by U.S. President Bill Clinton.

[6] By May 1998, Burton came under intense partisan pressure; even fellow Republicans complained that committee staff had published redacted tapes and transcripts of former United States Associate Attorney General Webster Hubbell's prison telephone calls omitting some exculpatory passages.

[16] They sued, unsuccessfully, for an injunction to prohibit the Federal Election Commission from enforcement of those provisions of BCRA on First Amendment grounds.

[19] In November 2020, following the conclusion of the 2020 presidential election, Trump recruited Bossie again to challenge ballot counting in states with tight margins.

[21] In February 2022, Bossie "spearheaded" a Republican National Committee resolution to formally censure Liz Cheney and Adam Kinzinger for their perceived disloyalty to Trump.

[24] He also wrote Intelligence Failure (Thomas Nelson, 2004), a book alleging that failings on the part of the national security apparatus during the Clinton administration led to the September 11, 2001, terrorist attacks.

[25] Bossie authored the "highly partisan" 2008 publication Hillary: the Politics of Personal Destruction, which is credited with delivering, in 2016, an insistent, long-term campaign theme to Trump of "LOCK HER UP!

The documentary, produced by Bossie for Citizens United Productions, had been written and directed by Steve Bannon, and was poorly reviewed by historians as "conceit", "fiction" and "pseudoscience".

[31] He also was ranked number two in Politico's top 50 most influential people in American politics in 2015, tied with Charlie Spies.