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Adolf Hitler punched
Adolf Hitler is the authoritative dictator of Germany and the leader of the Nazis in the TMNT comic book series, who is well-known for his actions in the Holocaust and World War II. 

History

Hitler's brain was still functionional decades after World War II and powered a time machine. Obtaining a robot body, Hitler travels back to World War II to find his past self. The Hitler from the future was destroyed by the Turtles while the Past Hitler tries to get the brain only to be punched by Raphael.

Hitler points a gun at the Turtles just as they were about to leave. Leonardo convinces Hitler that he is in Hell and they are demons that have come for his brains. They told the dictator that they already have his soul. Hitler shoots himself in the head so the Turtles can't recover his brain. 

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Comics
Shredder | Foot Clan | Karai | Baxter Stockman | Purple Dragons | Adolf Hitler | Leatherhead | Triceratons | Shredder Clones | Tokka & Rahzar | Alopex

1987 TV series
Shredder (1987) | Bebop & Rocksteady (1987) | Baxter Stockman (1987) | Krang (1987) | Rat King (1987) | Lord Dregg (1987) | Antrax (1987) | Barney Stockman | Don Turtelli | General Tragg | Groundchuck & Dirtbag | Alpha One | Krangazoids

Movies
TMNT 1 & 2: Shredder (1990) | Tatsu (1990) | Tokka & Rahzar (1990)
TMNT 3: Walker | Lord Norinaga
TMNT (2007): Stone Generals (Aguila, Gato & Mono) | Karai (2007)
TMNT (2014): Shredder (2014) | Eric Sacks | Karai (2014) | Baxter Stockman (2014)
Out of the Shadows: Krang (2016) | Bebop and Rocksteady (2016)

2003 TV series
Utrom Shredder (Tengu Shredder, Cyber Shredder) | Karai (2003) | Baxter Stockman (2003) | Tokka and Rahzar (2003) | Rat King (2003) | Drako | Ultimate Ninja | Hun | Sh'Okanabo | Dark Turtles | Viral | Commander Mozar | General Blanque | Lonae | Abigail Finn | Parker | Zanramon | Dragon Face | Yukio Mashimi | Weasel | Master Sliver | Savanti Romero | Agent Bishop | Triple Threat | Nanobot | Mephos

2012 TV series
Shredder (2012) | Karai (2012) | Rat King (2012) | Tatsu (2012) | Bebop (2012) | Rocksteady (2012) | Baxter Stockman (2012) | Antrax (2012) | Foot Gunner Ninja | Lord Dregg (2012) | Spider Bytez (2012) | Savanti Romero (2012) | Kraang Prime | Kraang Subprime | The Kraang | Kavaxas | Tiger Claw | Slash | Fishface | Rahzar | Newtralizer | Armaggon | Za-Naron | Justin | Pizza Face | Chrome Dome | Snakeweed | Dream Beavers | Speed Demon | Chimera | Koga Takuza | Spy-Roach