Joe Trippi has seen the future of presidential politics—and it's libertarian.

Trippi, the longtime Democratic political strategist who began his career working on Ted Kennedy's 1980 presidential campaign and is best-known for spearheading Howard Dean's Internet-fueled insurgency in 2004, says a strong run by a libertarian-leaning presidential candidate is inevitable. Four important changes in American politics are creating this opportunity: a socially tolerant public, the effective end of the two-party system, disruptive technologies, and the growing popularity of politicians such as Sen. Rand Paul (R-Ky.).

"The younger generation is probably the most libertarian and sort of tolerant, and has more libertarian values, I'd say, than any generation in American history," Trippi told Reason TV at a National School Choice Week event in San Francisco. An ardent defender of educational innovation, Trippi quips that he became a devoted proponent of school choice when he entered kindergarten at five years old.

When it comes to issues that are important to young voters – domestic spying by the N.S.A. and the legalization of marijuana, for example – libertarians are in touch with issues that the establishment won't go near, says Trippi. Public outrage has forced mainstream Republicans and Democrats to address the constitutionality of drone strikes and the expansion of presidential powers. But, he says, the political establishment will almost certainly do nothing more than tinker with a status quo that it helped to create.

That's why Trippi believes an outsider candidate should ditch the traditional two-party system and go it alone. As he demonstrated during Howard Dean's 2004 presidential run, a savvy candidate can leverage the Internet to mount a challenge from outside traditional pathways to power. Libertarian issues don't have enough support from within either party to win a presidential nomination, argues Trippi. But the Internet makes much of the partisan machinery irrelevant. He believes that crowdfunding is replacing $5,000-a-plate dinners and door-to-door campaigning is obsolete in the era of Facebook and "big data" analytics.

By taking advantage of these changes in American society, Trippi believes a candidate such as Rand Paul could mount a successful 21st century campaign. "[Paul] is so far the likely embodiment of who's going to raise the flag and take the hill," says Trippi. "[He] has a real shot at taking it." If Paul decides to run for president, Trippi projects "a fight of titans" against the establishment candidate at the Republican convention, comparing such a showdown to President Carter facing off against an insurgent Ted Kennedy at the 1980 Democratic convention.

Even if a libertarian fails to run outside of the established parties, Trippi is convinced that someone else will succeed. It's just a matter of time, he says, before we have a president who takes office without the backing of a political party.

About 22 minutes.

Produced by Todd Krainin. Cameras by Zach Weismueller. Interview by Krainin.

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