Of John the Baptist Jesus makes a strange declaration: Truly, I say to you, among those born of women there has arisen no one greater than John the Baptist. Yet the one who is least in the 
kingdom of heaven is greater than he (Mt. 11:11). This seems like a contradiction. Since everyone from Eve onward is born of women—and this includes everyone in God’s kingdom—then how is it that the least ones in the kingdom are greater than the greatest, John, who is the greatest one born of women? How can someone be greater than the greatest?
It is apparent that when He speaks of those born of women Jesus is speaking theologically, referencing those born with original sin. Similar language is found in the Old Testament. Psalm 51 states, Behold, I was brought forth [born] in iniquity and in sin did my mother conceive me. Job also declared, Man who is born of a woman is few of days and full of trouble (Job 14). Again consider Job 15:14, What is man, that he can be pure? Or he who is born of a woman, that he can be righteous? And again Job 25:4: How can he who is born of woman be pure? Notice the refrain, born of woman. In John 3 Jesus explains, That which is born of the flesh is flesh. Here Jesus simply reiterates what passages such as those quoted above are saying: To be born of women (of the flesh) is to be born in sin. St. Paul echoes: Those who are in the flesh cannot please God (Rom. 8). This can be paraphrased, Those born of women cannot please God, or Those standing in original sin cannot please God. Thus all born of women, including John the Baptist, are born corrupt with sin. Of course there was one exception: Jesus, conceived by the Holy Spirit, born exempt from original sin—is the exception. Yet Jesus explains that besides Him others born of women are—in His kingdom—greater than the greatest one born of women (John).
Simply summarized, in the Kingdom of God there is a new birth! In the great Baptism chapter (John 3), Jesus does not leave us with the words born of the flesh, for to this fleshly original-sin statement He adds,…that which is born of the Spirit is Spirit. United with Christ’s death and resurrection by faith, these citizens of the Kingdom of God are born again, born from above, born of the Spirit. This new birth is also set forth by Christ’s Holy Apostles: He saved us by the washing of new birth (Titus 3); You have been born again, not of perishable seed but of imperishable seed (1 Peter 2).
John the Baptist was indeed the greatest born of women; he stands as the greatest one born possessing the curse of original sin. But now those in the kingdom of God, even those who are the least—like babies—are born again to be greater than John because their new birth transcends their mother-birth into original sin.
How can this happen? How can we, or any sinner be greater than John? Indeed John and all other Old Testament believers were justified as they believed in the coming Christ. Yet the Christ must come and accomplish salvation. John and the entire Old Testament direct us to Jesus, the One born outside of original sin. The Father then made him who knew no sin to be sin for us that we might become the righteousness of God in Him (2 Cor. 5). Jesus bore our sin—including original sin—in his body on the tree. This is how we, or any Christian can be greater than John—by being united to the crucified and risen Jesus. Via faith-establishing Baptism we are united with the sinless One, the One who paid for our every sin. Only Jesus is greater than John, but because we are found to be in Christ Jesus in Holy Baptism, we too are greater than John.