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The first national income tax was enacted in the Civil War. The Internal Revenue Commissioner at the time didn't much care for it, according to this letter linked by the Tax Policy Blog:
I regard the tax as the one of all others most obnoxious to the genius of our people, being inquisitorial in its nature, and dragging into public view an exposition of the most private pecuniary affairs of the citizen.
The author of this letter had, like so many members of the Grant administration, served in the civil war. Alfred Pleasonton led Union forces in the largest cavalry battle ever, at Brandy Station at the start of the Gettysburg campaign. He also led Union forces in the largest civil war battle near Iowa's borders, the Battle of Westport near Kansas City (not to be confused with the Battle of Westport re-enacted annually by Cyclone fans during the Big 12 basketball tournament).
The letter didn't help General Pleasonton's civilian governmental career:
As a civilian, he worked as U.S. Collector of Internal Revenue and as Commissioner of Revenue, but he was asked to resign from the Internal Revenue Service after he lobbied Congress for the repeal of the income tax and quarreled with his superiors at the Treasury Department. Refusing to resign, he was dismissed.
By this time he should have known better than to talk back to U.S. Grant...
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