
Wine & Song
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I must say the “actually” in this prompt feels a bit accusatory and judgmental — as though, as a matter of practice, the answerer is generally unreliable. It also sounds like a question for someone with Dissociative Identity Disorder — otherwise who is making promises to whom? I am either one being or I contain multitudes, there being two seems at once too crowded and too lonely.

I’d lean flawed but interesting — e.g. Sun Wu Kong, Artful Dodger, or Juliette (of the same-named Sade novel [not the Shakespearean one,]) but it is risky. The Monkey King might bash me, Artful Dodger might rob me, and who knows what Juliette might do. So maybe the Candide from the end of the book.

I can’t claim I’ve ever done as well as Peter Minuit (buying Manhattan for $24) or Thomas Jefferson (picking up the Louisiana Territory at $0.04 / acre,) or the USG (acquiring Alaska for $0.02 / acre.)
I once bought a nice stick (which still have,) but it was not a tremendous bargain.
What If? 2: Additional Serious Scientific Answers to Absurd Hypothetical Questions by Randall Munroe