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Jefferey Eugenides’ Middlesex raises the issue of transnationalism and transgender through the combination of Greek immigrant narrative and the narrator, Cal, so called ‘hermaphrodite’s’ buildungsroman narrative. Lefty and Desdemona Stephanides, the first generation immigrants fail to be assimilated into American subject. Although Lefty gets a job from Ford company and tries to be a ‘perfect American citizen’, he cannot go into American mainstream society, whereas Desdemona rejects to accept American subjectivity and remains an “eternal exile” to the end. The failure of the first generation reveals the way American national culture operates to separate and exclude inferior or inadequate immigrants. Milton Stephanides, the Second generation represents himself as a “perfect American”, and to fulfill it he adopts the strategy to differentiate himself from African-American and mainland Greek people. His attempt to deny and erase the effect of transnational relationships embedded in his life leads to disruption and fissure in his being. Cal(liope), the third generation has 5-Alpha-Reductase Pseudohermaphrodites caused from the frequent incest tradition. He crosses the border between genders as his grandparents crossed the border between nations. This analogy raises an objection to the absolute of borders to circumscribe subjectivity such as nationalities, genders, ethnicities, etc. Although Cal chooses to perform the straight-man, he still contains the contradictory and discontinuous elements within his self and it makes him unstable and changeable diaspora subjectivity.