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The biggest takeaway is that his name is actually not Stratechery. Why on earth would you name your site something so extremely hard to parse?

It’s a portmanteau of the authors two favorite things: Stratego by MiltonBradley and Treachery. Something about cheating at board games.

(And the domain was available)

I thought it was based on the Bush-ism "strategery" - https://stratechery.com/2013/strategery/

Or was that a later change?