The New Testament and the Roman Empire intersect during the first century. As Romans expanded their control, Jews were forced to adhere with two different sets of law. Beside the Torah, the first five books of the Old Testament, non-Roman citizens needed to comply with Roman law or else face punishment.
If anyone forces you to go one mile, go with them two miles, Matthew 5:41.
One law required a Jew to carry a Roman’s belongings or possessions for a Roman mile if asked to do so. A Roman mile is one thousands paces, equivalent to 1,000 yards, or 660 yards shorter than a modern day mile. During the Sermon on the Mount, Jesus encourages his audience to do more than a Roman mile, going above and beyond what a Roman citizen asks you to do.
Give to the one who asks you, and do not turn away from the one who wants to borrow from you, Matthew 5:42.
Jesus didn’t ask his followers to do anything without first modeling it within his own life. Several New Testament passages refer to Jesus as a servant of God, laying down his life for others. Jesus understood that preaching and theology doesn’t convince non-believers to enter into a personal relationship with God. Rather, lives are transformed when the love of God is displayed daily through a spirit of servant-hood. Therefore, if you want to leave a lasting legacy on earth, emulate the Roman mile by giving of yourself to those who ask, need or appear to require some sort of help. This is what Jesus means by going the extra mile.
by Jay Mankus