How easy is it to make an anarchist syndicate in the middle ages?

[Shades of Eternity]

Seriously curious after watching this.

 

[Theory of Games]

Uh. They call it comedy for a reason. Anarchists are hated in the modern world. In the Old World, they were tortured and burned. Publicly.

 

[MGibster]

I think the key here was the following:

1. Marginal land not particularly suited to agriculture or industry.
2. The land had no strategic value.

I could see the crown just deciding to leave something alone because it's just not worth the trouble to mess with it.

 

[Tonguez]

There were a few religious communes during Medieval times that had Anarchosynicalist tendencies - most notably the Taborites, the English Ranters, the Adamites and Brethren of the Free Spirit.
They tended to religious reformers who formed communes, were anti-establishment, got accused of immoral behaviour resulting in them being declared heretics and thus getting stomped out by the establsihed Church.

So yes quite possible, especially if your world is Polytheist and thus lacking a tradition of anti-heretical Crusades.
Monarchs are too busy doing politics to concern themselves with a few rural communes with weird ideas (at least until they start murdering virgins and summoning demons)