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Re:For $1B, Elon Musk’s Tunnel to O’Hare Would Be a Miracle by cassieramen on Friday June 15, 2018 @12:58PM (#17321353)
It's important to remember that the federal government was actively subsidizing the urban exodus to suburbia in the 1940s. The subway became unprofitable due to federal housing policy and the local or state government ended up having to bail it out.
Re:For $1B, Elon Musk’s Tunnel to O’Hare Would Be a Miracle by pg_bot on Friday June 15, 2018 @01:28PM (#17321657)
The NYC subway became unprofitable due to the terrible contracts that the operators signed.[0] Specifically they could not increase the fare greater than five cents, which doomed them because of inflation. The city took over the BMT and IRT companies on June 1st 1940. Suburbanization did not really start occurring in the US until after the end of WW2.

[0]: https://en.wikipedia.org/wiki/Dual_Contracts#Conditions