Bossie grew up in Massachusetts. He attended Towson State University and the University of Maryland, but dropped out before graduation. When he was 18 years old he volunteered in Ronald Reagan's reelection campaign.
A volunteer firefighter in his youth, Bossie dropped out of university to pursue politics. Bossie was the youth director of Sen. Bob Dole's 1988 presidential campaign.
After the Republicans won control of the United States House of Representatives in the 1994 elections, Dan Burton (R-IN) became chairman of the House Committee on Government Reform and Oversight. In 1997, he hired Bossie as chief investigator to look into possible campaign finance abuses by U.S. President Bill Clinton.
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. Speaker of the House Newt Gingrich pressed Burton to seek Bossie's resignation. Shortly thereafter, Burton accepted Bossie's resignation.
During his tenure at Citizens United, which he had joined as a researcher after Bill Clinton was elected in 1992, the organization focused increasingly on producing film documentaries through its Citizens United Productions division. Their films have included:Border War: The Battle Over Illegal Immigration
Rediscovering God in America, hosted by Newt and Callista Gingrich
Hillary: The Movie
Citizens United hoped to begin distribution of the feature film Hillary: The Movie in January or February 2008. The Bipartisan Campaign Reform Act of 2002 made that an unlawful electioneering communication. They sued, unsuccessfully, for an injunction to prohibit the Federal Election Commission from enforcement of those provisions of BCRA on first amendment grounds.
In a 2010 landmark decision, the Supreme Court decided Citizens United v. Federal Election Commission for Citizens United. For-profit and not-for-profit corporations may now advertise and broadcast messages of a political nature without limits on how much they can spend and with few limits on the timing and nature of the messages.
In September 2016, presidential candidate Donald Trump hired Bossie to be his new deputy campaign manager.
Bossie is the author of The Many Faces of John Kerry, a critical look at the Democratic nominee in the 2004 presidential election, then-Senator John Kerry. He has also written Intelligence Failure, a piece alleging failings on the part of the national security apparatus during the Clinton Administration in the years before September 11, 2001. Bossie is also the author of the 2008 publication Hillary: the Politics of Personal Destruction and co-author of the 2000 release Prince Albert: the Life and Lies of Al Gore with Floyd Brown.
At the Tea Party Convention, Bossie debuted the documentary Generation Zero, focusing on the 2008 financial crisis and its basis in the selfishness of the Baby Boomer generation. Said documentary, produced by Bossie for Citizens United Productions, had been written and directed by Steve Bannon.
David met his wife, Susan, through his political work. They reside in Montgomery County, Maryland with their four children. Bossie received the Ronald Reagan Award from the Conservative Political Action Conference in 1999. He also was ranked number two in Politico's top 50 most influential people in American politics in 2015, tied with Charlie Spies.