As a kid I played a game called Secret Weapons of the Luftwaffe, a flight sim by LucasArts designed by the guy who would later do X-Wing and TIE Fighter (I guess the latter was also bad because you fought with the space fascists). You could fly all kinds of Nazi planes that never saw action in real life like jet fighters, and it wasn't until much later whenI realized that glorifying cool Nazi superweapons was bad, actually.
Same with Panzer General, which was a fun lite strategy game otherwise, but you literally played as Nazi Germany. I can't believe that actually wasn't considered a big deal at the time.