Milwalkee flag, which has a flag on the flag. The seal is not much better either:
chief Pocatello of the Shoshoni Tribe who gave the railway right of passage through his reservation. I did think of adding my ferroequinology crown to reflect the railroad which seems to have played an important part in the foundation, but thought it might take away from the feathers, so I decided against it.
The flag is based on a banner of the coat of arms but turned onto its side:
It is certainly way better than the current flag, if nothing else.