Raimondo described himself as a "bad kid"; to deter himself from this path he spent one year at a Jesuit-run school in upstate New York.

He "joined the party in 1974, and was active in Roger MacBride's 1976 presidential campaign, the LP's second White House bid.

After 1989, Raimondo again began working with Rothbard in the anti-war, paleoconservative John Randolph Club, part of the Rockford Institute.

[9] In 1982, Raimondo ran for California's 5th district seat in the United States House of Representatives as a Libertarian, against Democratic incumbent Phillip Burton and Republican challenger Milton Marks.

While he championed conservative and libertarian causes in general, the main emphasis of his campaign was his opposition to the deployment of U.S. troops in the Balkans and, in particular, Pelosi's vote to that effect.

"[16] In 1994, Raimondo was the San Francisco coordinator for the "Save our State" Proposition 187, which would have barred taxpayer funding of non-emergency services to illegal aliens in California.

"Nader’s distrust of bigness, either corporate or governmental, his fear of centralized power, his sharp critique of the managerial-bureaucratic mentality, all recall the distinctively American tradition of individualist populism", he wrote.

[19] Raimondo wrote positively about Ron Paul's 2008 presidential campaign, but expressed support for Dennis Kucinich.

[23] Raimondo argued in a 2003 Antiwar.com column that Israel exerts a dominant force in the formulation of American foreign policy.

[30] He also argued that after years of persecution by the state, LGBT rights activists sought to "use the battering ram of government power" to actively intervene on behalf of homosexuals.

"[32] Raimondo further described his early interactions with the Catholic Church and a local Jesuit seminary in Yorktown Heights as being influential in his development, despite rejecting the notion of God.