This paper delves into the gender trouble of John’s Jesus in comparison with the gender trouble of Philo’s Sophia. The paper argues that Philo employs a strategy to masculinize Sophia and eliminate her femininity, whereas John uses a strategy to stress Jesus’ masculinity as Logos and conceal his femininity as Sophia. On the one hand, Philo represses Sophia’s feminine traits by representing her as a father of virtues (De Fuga et Inventione 51-52). Nevertheless, Philo is well aware of a conflict of gender in Greek grammar between Logos as masculine and Sophia as feminine. In Philo’s view, Sophia as the daughter of God and the father of virtues interchangeably plays a female role in relationship with God and a male role in relationship to humanity. Thus, Philo portrays Sophia as alternating between male and female roles rather than as bisexual. On the other hand, the writings of Philo shed invaluable insight into the en-gendering of John’s Jesus in a Hellenistic Jewish context. In this light, Jesus, the enfleshed Logos, can be seen as Sophia on a hidden level. Due to the gender problem to consider Jesus as both the masculine Logos and the feminine Sophia simultaneously, John’s Gospel seeks to erase Jesus’ femininity and stress his masculinity by dropping the Greek feminine term Sophia and stressing the Greek masculine term Logos. However, Jesus crosses gender boundaries by taking on feminine imagery relating to delivery throughout the Gospel. The birthing image (John 16:21) can apply to Jesus’ symbolic act of giving birth to God’ children in the crucifixion narrative (John 19:34). Thus, Jesus, as a male character, crosses over the lines of gender that divide femininity from masculinity by performing the feminine role of childbirth.