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Based on my (probably wrong) math, either a penny or, like a 2 cent coin (those existed at some point, right?).
So the ratio of old money to new money is approximately .25 to 4.50, which means that the value of money has shrunk by a factor of about 18.
25 cents over 18 yields ~1.38 cents.
So if he took a penny, cut it into thirds, taped one of those thirds to another penny, and was able to flip that unbalanced mess, you could say he'd lost a modern quarter's worth of value.
I joked a quarter-sized penny. I call it: the ~~poorter~~ pennyce