Notice he corrected himself…”set sail…(guffaw) astride the open roads”
ahhhno sailing ship! Road travel!
So I wonder what pirates astride on the open roads with if they don’t a ship. Horses? Carts & mules? Just walking? They would be more like Robin Hood & his merry men without the “giving to the poor” part.
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Nothing is impossible on OUAT. Everything has a way of repeating itself. Keeper of the Keeper tread: https://oncepodcast.com/forums/topic/official-keeper-thread-3/#post-217924