In modern times?
Korematsu v. United States (1944)
SCOTUS affirming that the US could detain people in concentration camps and confiscate their property on the basis of ethnicity.
this post was submitted on 26 Jun 2025
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Kelo v. City of New London.
It solidified expanding eminent domain from the previous traditional uses like national defense to a low and nebulous bar of "might be good for the economy I guess maybe", and more egregiously rather than transferring the land from a private owner to the government, the case was about transferring from private owners to a corporation (other private owners) backed by the government's power to do so and justified somehow as public use.
As an aside, the resulting development was an economic dud which really added insult to injury.
I ain'ts much of a fan of Wickard v. Filburn and Schenck v. United States neither.