"I'm a hardcore libertarian - I want everything legal - but I also believe that you have the right to free association"

Penn Jillette’s statement reflects a nuanced and deeply principled perspective on liberty, focusing on two essential pillars: the legalization of all consensual activities and the uncompromising right of individuals to associate, or not associate, freely. The notion of wanting “everything legal” points toward a radical version of classical liberalism or libertarianism, which insists that the government’s role in regulating personal behaviors should be minimized. Whether regarding drugs, speech, business practices, relationships, or other voluntary activities, Jillette advocates for a society where laws do not infringe upon individual autonomy unless there’s a clear victim.

However, his commitment to freedom does not stop at personal choices; it extends to the realm of social interaction. The “right to free association” is just as crucial as legalization. This right protects not only the liberty to join groups, organizations, and partnerships but also to refuse or withdraw from them. Such freedom guards against the imposition of forced relationships, whether by government or societal pressure. For Jillette, authentic liberty is impossible unless people can select both their actions and their company.

This dual stance can lead to uncomfortable or controversial outcomes, some associations or rejections may be offensive or exclusionary. Yet, by holding both principles, Jillette contends that a truly free society must tolerate expressions of freedom that are both personal and social, so long as they do not involve coercion. It is not the government’s place, in his view, to conscript people into associations (like membership, commerce, or partnerships) against their will, any more than it should tell them which personal behaviors are permitted.

Ultimately, this view champions responsibility and tolerance. By legalizing all consensual behavior and defending free association, society must learn to accept a greater diversity of choices and relationships, trusting that voluntary interaction is necessary for a genuinely free and pluralistic community.