What exactly is up with the very western edge of Kentucky? Just south of New Madrid is like an isolated Kentucky that isn't even connected to the rest of the state in any way. What is up with that?
My guess is that it's vestigial from when the boundaries of the states (or territories at the time) were first laid out. The border between KY and TN was probably delineated first, as a certain line of latitude, and then when western borders were needed the Mississippi River was the obvious choice. No one probably even realized that those boundary definitions left Kentucky with a weird little exclave like that until it was too late (and IIRC it takes some kind of practically impossible legislative process to change the existing boundaries of an established state).
In other places, changes in course in the Mississippi River have left chunks of east-bank states on the western side of the river and vice versa.
https://en.m.wikipedia.org/wiki/Kentucky_Bend
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We had a fairly lengthy thread on this a few years back:
https://www.aaroads.com/forum/index.php?topic=577.0