Libertarianism is anti-democratic because it attempts to negate “the association of the nation”, which is how Paine defined government. Libertarianism is the feeble step-child of anarchism: espousing that the individual is everything, the collective is always oppressive.
Anarchism denies the sociability of humans and the strength that it inures; instead, anarchism only sees individuals, alienated from each other, gaining no advantage from what Paine sees as the natural instincts of humans to form social bonds, and those bonds forming the basis for the national association of government.
In Paine’s view, it is government, and not its absence, that should be the enforcer of rights. To protect an individual’s rights can only be done collectively. All of Paine’s governmental proposals start with a constitution clearly defining rights. Government should not be a negative, but a positive force for human rights. In comparison to monarchy and mixed government, a simple, direct efficient government can only be attained by democratic representation and democratic implementation, according to Paine.
Libertarianism grew out of the philosophies of oligarchy. It follows from John Jay’s “the people who own the country should run the country” statement, and John Calhoun’s “I have the freedom to own slaves”. It is applied anarchy of restricting government, Reagan’s “government is the problem”, but putting the elite in charge at the same time: i.e., individualism should rule, collective goals are a denial of freedom. That is the mantra, leaving the wealthy as the only ones in a position to exert power.
This has real, modern impacts, mostly through well-funded think tanks of the rich, the Heritage Foundation, the Federalist Society, Cato Institute, and others. All founded in the 1970s to promote the ideologies of the previous paragraph. The architect was James Buchanan (not the President, the philosopher from the University of Chicago who implemented many racist economic policies – if you haven’t read MacLean’s Democracy in Chains you should). Buchanan was the ideologue behind these right-wing think tanks. He created the politburo of the right-wing structures, set up to deny democratic hopes. Libertarianism is their language.
This gets us back to the first principles of Paine: individuals can only achieve their rights collectively, otherwise only the rich can thrive. If everyone has equal rights protected by the government, that government must be democratic, and vice versa. Buchanan is the reverse of Paine. The wealthy should rule, the individual who is wealthy should rule.
Collectively, the wealthy are outnumbered, and one-person-one-vote makes them meaningless. How can they hang onto their obscene wealth like that?! When Buchanan was sent down to Chile in 1980 to write their constitution that was imposed on the people of Chile, he made wealth exempt from government regulation or even appropriate taxation.
So when Libertarians say they love Paine, they contradict themselves, or they haven’t read Paine.