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My criteria is how a decision affects the control of the individual by the State. In that regard Dred Scott has to stand out as the greatest miscarriage of justice in American history.

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.

The Dred Scott case shot down an attempt to undermine slavery in the territories, and Tawney's opinion included some racist thinking, but it didn't create slavery which had been supported by the legal system for 200 years by then. If anything it helped bring on the Civil War and therefore the end of slavery.

If Roe v. Wade was libertarian, so was Dred Scott--at least for the slaveholders. The Dred Scott decision did not trample on the rights of the states as Roe and Kelo did.