Adding Omaha's county to Iowa would make both NE and IA more Republican... but would probably help Democrats on balance, by moving one electoral vote to a tilt-Dem state. Super-paradox!
Not really, as making two states more Republican(/Democratic) necessarily adds more population to the more Democratic(/Republican) of the two. Will Rogering states ain't a free lunch.
It's a paradox in the same way that the Will Rogers paradox is a paradox.
But it's not always the case that making two states more D via the Will Rogers paradox will actually help the R's. For instance, the example above where a light-blue county in Illinois goes to MO, making both states more D, would tend to help the Dems - they'll gladly trade the 1 guaranteed EV for a better shot at all of Missouri's.