A couple questions about Illyrio. I’m unclear exactly why he is called the cheesemonger, since he seems to deal in far more rarified materials than cheese. And why does he care so much about who rules Westeros? Does it truly benefit him that much to devote some fifteen to twenty years creating a precarious plan to get someone whose ear he can whisper to whenever he wishes on the Iron Throne? The same goes for Varys, for that matter…

Cheesemonger is an insulting title, used by Tywin and people with his prejudices as a way to belittle the magisters of Essos, who by their very existance undermine the strict distinction between nobleman and merchant. Magisters deal in exotic goods, fine manufactured goods (a sign of Essos’s economic and technological superiority), and complicated financial transactions that nobles don’t understand. So treating them like common peddlars like the ones in Westeros creates a sense of the social order restored.

As to why Illyrio cares, I have a theory about that…

Simon Rumble Asks: Cheesemonger

How rich is Illyrio? Where does it all come from?

Extremely rich, although less rich than Xaro Xhoan Daxos. But enough to become a Magister of Pentos and marry the sister of the cousin of the Prince of Pentos. So he’s definitely in the top 1% if not the .1%. 

In terms of where the money comes from, he took the nest egg he and Varys built from their various schemes and invested it into “spices, gemstones, dragonbone, and other, less savory things.”