[x]

St Louis is a physically small city that has lost well more than half of its population and probably 3/4 of its tax base in the last half century.

The 1876 vote to separate from St. Louis County was one of the dumbest ideas ever. The city didn't want to pay for services in outlying areas. Apparently nobody foresaw the later growth of suburbs.

[hanamizu]

Well, to be fair to the civic leaders in 1876, separation probably worked pretty well for them for the next 75 years or so. I think the city reached its peak population in the 1950 census. But in the long long run, it doomed the city. As things got worse, many who could fled to the county leaving the city with thousands of empty buildings.