Trippi served as Deputy Campaign Manager for Los Angeles Mayor Tom Bradley's successful reelection bid in 1981 and his unsuccessful run in the 1982 California gubernatorial election.

[16] Trippi worked on a number of recent House victories for Representatives Tulsi Gabbard, Janice Hahn, Mark Takano, and Seth Moulton.

[18] The campaign overcame millions in outside spending to beat 18-year incumbent John Tierney in the primary and Richard Tisei in the targeted general election.

[19] In a 2015 article from The Boston Globe, Moulton recalled nationally renowned pollster Mark Mellman telling him to quit the race because it would be "statistically impossible" to win.

[20] In 2017, Trippi worked on the special election to fill the Senate seat vacated by Jeff Sessions on behalf of former US Attorney for the Northern District of Alabama Doug Jones.

held by incumbent Roger Wicker,[22] and with former Secretary of Agriculture Mike Espy in the special election for the Senate seat vacated by Thad Cochran who decided to resign for health reasons.

[23] In 2018, Trippi worked on the campaign of Janet Garrett, a retired schoolteacher and union leader running to unseat the conservative founder of the Freedom Caucus, U.S. Rep. Jim Jordan, in Ohio's 4th congressional district.

[28] In 2008, Trippi helped Morgan Tsvangirai and Zimbabwe’s opposition party, the Movement for Democratic Change receive the most votes over Robert Mugabe in elections marred by violence.

[29] He also brought media attention to Mugabe’s democratic subversion and violence which led to a unity government and Tsvangarai becoming the Prime Minister of Zimbabwe.

Trippi remained in California to hold his first and only government position as Lieutenant Governor Leo T. McCarthy's Deputy Chief of Staff,[10] before overseeing several successes in Vice President Walter Mondale’s 1984 campaign for the Democratic presidential nomination.

[43] Following the Mondale campaign, Trippi joined Senator Ted Kennedy’s PAC, the Fund for a Democratic Majority, as Deputy Director under Paul Tully.

[45] In 1987, Trippi left Doak and Shrum to work on Gary Hart’s 1988 presidential bid with former colleague Paul Tully as deputy political director.

[50] There, Trippi was instrumental in the creation of the "Hyundai" ad, a television spot which received praise for launching Gephardt from last place in the polls to winning the Iowa caucuses.

[61] Through this innovative use of the Internet for small-donor fundraising, "Dean for America" raised more money than any Democratic presidential campaign to that point – all with donations averaging less than $100.

[63] He also worked as media strategist and a senior adviser[64] for Doug Jones' successful campaign in the 2017 U.S. Senate special election in Alabama, running for the seat left open when Jeff Sessions was appointed as Attorney General.