Let’s rephrase the question:
“If Jesus were really counter-cultural, why didn’t he choose any Gentiles to be his apostles?” or “Why didn’t he choose any slaves as apostles?” Jews thanked God that they were not born a Gentile, an untrained person (or a slave), or a woman, so wouldn’t Jesus have been really counter-cultural if he had Gentiles and Jews, untrained and trained (or slave and free), and women and men among his twelve disciples? Paul refers to the equality of all believers (Gal. 3:28), and recognized the ministry leadership of Titus, a Gentile; Onesimus, a slave; and Phoebe, a female. Were Paul and Jesus’ other disciples more counter-cultural than the Lord they followed? I think not. Perhaps we need to understand further the significance of the twelve for Jesus.
Twelve Jewish men symbolized the patriarchs of the twelve tribes of Israel (Luke 22:30). Jesus’ own call to ministry was focused on reaching Israel (Matt. 10:5–6; 15:24; John 1:11; Rom. 15:8–9), because the earlier covenant was made with Israel (see Gen. 35:10-12; 1 Kings 18:31). The twelve were a witness to Israel, representing God’s first covenant with them and reminding them of God’s promises that were about to be fulfilled through Jesus.
The twelve do not, however, signify that only men can be leaders in the church. Nowhere does Jesus ever state that only men may serve as leaders in the church, nor does he teach that it is by maintaining traditional male-female roles that we will advance God’s reign. Jesus’ teachings do not focus on the apostles’ ethnicity or sex as a model for Christian leadership. Otherwise no Gentile church could have its own leaders but would have to depend on Jewish males to lead each congregation. Also note that after Matthias replaced Judas, the twelve were not replaced once any of them died after Pentecost (such as James, son of Zebedee, Acts 12:2). Jewish male apostles are not synonymous with all leadership, and nowhere does the New Testament teach that other categories of leaders (like overseers, 1 Tim. 3:1) should be clearly limited to apostles.
Building on this Old Testament symbolic base of the twelve, Jesus began expanding the numbers for the new covenant. The new covenant was begun by the apostolic witness of women and men. An apostle is someone sent with orders, an eyewitness of the resurrected Jesus. Jesus commissioned the twelve to “be with him” and he sent them “to preach” and “to have authority to drive out demons” (Mark 3:14–15). To “be with” Jesus, therefore, preceded the sending. After the resurrection, “apostles” were comprised of many who had “been with” Jesus and were now also witnesses to the resurrection (Acts 1:21–22; 4:33), including the women at the tomb (Matt. 28:1, 7; Mark 16:1, 6–7; Luke 24:5–10) and the more than 500 brothers and sisters (1 Cor 15:6). In the post-resurrection, post-Pentecost new covenant community, apostles are no longer limited to twelve, but are multi-numbered because Jesus’ ministry has refocused from the Jewish people, the twelve tribes, and the old covenant, to the Gentiles, the nations, and the many tribes. At Pentecost, the Holy Spirit became a permanent indweller of every believer, thus equipping every believer — both male and female — to be priest or intercessor between humans and God (1 Peter 2:9).
Moreover, we have examples of female apostles in the New Testament. Jesus sent out Mary Magdalene, saying to her: “Go to my brothers and sisters and say to them, I am ascending to my Father and your Father” (John 20:17). He broke convention by choosing women as the first witnesses for the greatest event of all times, the resurrection, even though women were not considered as valid witnesses in court. He established that faith — not ethnicity, class, or gender — is the key determiner of service and leadership in the new covenant community.
Additionally, one woman, Junia, is even called an “apostle”: Paul describes “Andronicus and Junia, my compatriots and my fellow prisoners, who are well known (episemos) among the apostles, they also came before me in Christ” (Rom. 16:7). Episemos is literally “having a mark.” Andronicus and Junia “stood out” or were “important,” “marked out,” among the apostles. They were believers, witnesses of Jesus’ resurrection, who stood firm despite persecution and imprisonment in the message they were given about the Messiah.
For further study, see Aída’s chapter (7) in Discovering Biblical Equality: Complementarity without Hierarchy, as well as chapter two in her book Beyond the Curse: Women Called to Ministry. Both are available at cbebookstore.org.