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What made you think he bought Windows? He's the founder of The Pirate Party after all :P

1) He used to work for Microsoft.

2) He's got the money to pay for it.

3) It would be incredibly stupid of him to flagrantry violate copyright and commit a crime. Rick is many things, but stupid is not one of them.

The VM is an old Windows XP that I bought (legitimately!) for $10 as a Microsoft employee. Perhaps it was $15. Thereabouts, anyway.