Would any debt be transferred to the County when the City joins it?

Specifically: "Would any financial responsibility for any current City of St. Louis obligation (either debt or leasehold) automatically transfer from the City to the County if the City re‑entered the County as a municipality?"

Answer

Nope.

From Polsinelli:
"No, there are no currently existing City of St. Louis obligations which would automatically become the partial or full responsibility of the County, were the City to re-enter the County as a municipality."

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