Although it can seem paradoxical today that the federal government redistributes from “blue” states where majorities are tolerant of federal taxation to “red” states where they are hostile, the rhetoric was more straightforward in the politics surrounding the adoption of the Sixteenth Amendment a century ago. In fact, Southerners and Westerners demanded the adoption of the federal income tax for the obvious reason that it would benefit their constituents. By exempting income taxation from the apportionment rule that the Constitution specifies for “direct taxes,” the Sixteenth Amendment allowed Congress to tax in proportion to the distribution of income rather than the distribution of population. Because of the lopsided geographical distribution of income at the time, this procedure generated lopsided contributions from the high-income states of the Northeast, particularly New York. Yet some Southerners also thought the income tax was potentially dangerous because it would strengthen the federal government, with results that could potentially threaten their oppression of African Americans (disfranchisement, segregation, and rampant lynching). White Southerners worried about the safety of white supremacy in their debates with each other about whether to ratify the Sixteenth Amendment. In the end, however, they ratified enthusiastically, not only because they knew that their states would benefit, but also because they believed, correctly, that Northerners had lost interest in attempting to protect the rights of African Americans. Thus, this milestone in the history of taxation exemplified the irony of the Progressive Era.