On the outbreak of the Second World War he produced several racist and anti-semitic posters that targeted the allies. This included one poster that referred to African-American soldiers in the United States Army. As Mark Bryant has pointed out in his book, World War II in Cartoons (1989): "In Gino Boccasile's famous Italian poster depicting the cultural barbarism of the American troops, the black American sergeant, his features transformed nearly into a gorilla's face, grasps Greek art treasures, ludicrously under priced with animal savagery."
Anthony Rhodes has argued: "Their propaganda about barbarian mercenaries in the British army was supplemented when the United States came into the war by Boccasile's famous poster of an American black G.I. carrying off the marble statue of the Venus de Milo with a $2 price ticket attached to its neck. The Americans would plunder and destroy the cultural treasures of the more civilized continent."
Later that year Boccasile was arrested and imprisoned. He was later tried for crimes committed during the war. Although he was acquitted, he had trouble getting work as an illustrator. However, he eventually set up his own agency in Milan.