Wickard V Filburn - blew a hole in the constitution that opened the way for the imperial Federal Government.
http://en.wikipedia.org/wiki/Wickard_v._Filburn
Plessy v. Ferguson, if I understand the case correctly, said the the State had the right to pass laws that mandated private companies to provide separate but equal accommodations. While it might have been wrong and unjust, it did not take away the rights of blacks to move freely and travel via rail.
Roe v. Wade did not further the State's power to control personal decisions. The legal reasoning may be suspect, but it was in a way a libertarian decision.
Kelo allows the State to take whatever it wants, at any time. The fact that they have to pay compensation is of little value since it's not a real transaction in the sense a private deal is.