What case invalidated an earlier effort by Congress to enact a federal income tax?

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Pollock v. Farmers Loan & Trust Co. (1895) invalidated an earlier effort by Congress to enact a federal income tax, ruling that taxes on income from property were direct taxes and had to be apportioned among the states according to population, which effectively made a federal income tax unworkable under the existing constitutional framework.

What Case Invalidated an Earlier Effort by Congress to Enact