In Delgadillo v. Carmichael, the U.S Supreme Court ruled in favor of an immigrant who had been ordered to be deported due to a criminal conviction. The case revolved around Ignacio Delgadillo, a Mexican national and legal resident of the United States since 1919. During World War II, he was convicted for a minor offense and served time on a ship outside U.S territorial waters as part of his punishment. After his release from prison, immigration authorities sought to deport him under an old law that allowed deportation for immigrants "leaving" the country after committing crimes involving moral turpitude. The court held that serving time on a ship outside U.S territory did not constitute "leaving" the country within meaning of this law because it would lead to absurd results if interpreted literally - such as considering someone leaving US when they were involuntarily taken out by government order or force majeure events like storms etc., which is against common sense understanding of term 'leave'. Therefore, Delgadillo could not be deported based on this provision.

In the dissenting opinion for Delgadillo v. Carmichael, Justice Frankfurter argued that the majority's interpretation of "entry" in immigration law was overly broad and inconsistent with past precedent. He contended that a brief departure from U.S territory due to wartime service should not be considered an "entry," as it would unfairly penalize lawful residents who had served their adopted country during war time. He also pointed out that this interpretation could lead to absurd results, such as treating a resident alien who briefly left U.S soil on a fishing trip as if he were making an initial entry into the country. Furthermore, he criticized the majority for failing to consider legislative intent or policy considerations in its decision-making process.