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Comic: Young Allies #1
Year: Summer 1941
Back in 1941, Marvel gave Captain America's homeboy Bucky Barnes a squad of his own: the Young Allies. They were essentially his sidekicks, but one of them was a heinous racial stereotype brought directly to ink. While his given name was Washington Carver Jones, the character was sadly known as Whitewash Jones, which is not only odd but racist as hell.
Whitewash, while part of the crew, was apparently only good at "de watermelon" and could "make a harmonica talk." He looked like the worst minstrel show rendition of a black person and was a bumbling idiot to boot. He'd say shit like "gosteses" instead of "ghosts," and was drawn to look more like a monkey than an actual human being. At least he was fighting the Nazis?
Years later, Marvel retconned the whole damn comic book, saying that the series was sensationalized propaganda that even went as far as depicting Bucky's squad as 12-year-old kids as opposed to the grown men they really were during that era. Kudos to them for that, but what in the actual fuck?!