I'd go back to the start of the 1919 World Series in Cincinnati. I'd live off one of the dollars (I wonder what a 1919 hot dog would taste like?), and bet the other one of the Reds to win Game 1. The odds were 5 to 1 for the White Sox, which would pay me enough to make some more bets, and ultimately make a living off it (Hello Indians in '20, and Giants in '21!). I'd have enough pocket change pick up a few thousand T206s in nice shape, which were probably close to worthless at the time. I'd have to wait a while for gum cards to be invented, but I'd have a glorious time getting in on the ground floor of the Roaring '20s.
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