Beginning in 1992, Bossie joined Citizens United as a researcher, during which time Citizens United produced many films promoting Republican perspectives and talking points. Later in the 1990s, Bossie had a troubled turn as congressional investigator. 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. In May 1998, bipartisan concern mounted over inappropriate redaction of tapes and transcripts of former U.S. Associate AG Webster Hubbell's prison telephone calls omitting some exculpatory passages. Newt Gingrich pressed for Bossie's resignation which followed shortly thereafter.