Palo Alto has the dumbest city boundary I have ever seen.

Richmond's probably second. Looks like someone just carved out their neighborhoods and was like "im out!"

It wasn't about "carving out" tho, more so resisting annexation.

These maps were mainly just big cities annexing places and some places accepted it, others refused. @berkeleyside April fools map shows what a perfect square Berkeley would be if Albany had been annexed

Of Course, Oakland the Donut with a rich, creamy white donut hole named Piedmont and a long custard donut named Alameda

Peninsula is just all bad https://twitter.com/cafedujord/status/1253020251165351936?s=20

I define dumb as a city whose boundaries look like they have some insidious or bygone dumb reason behind existing.