A devoted disciple of Yeshua will give you “the shirt off his back” and he will always “go the extra mile” for you. Both sayings appear in the context of Yeshua’s sermon about entering the kingdom of heaven. Those seeking to enter the kingdom are willing to go beyond the minimum required of them.
Yeshua taught His disciples to go beyond the letter of the law in showing deference for others, even setting aside their own legal rights and prerogatives for the sake of the kingdom. He said, “If anyone wants to sue you and take your shirt, let him have your coat also” (Matthew 5:40).
In a Roman court of law, a creditor could literally demand the shirt off of a debtor’s back. Rather than resist the litigation, Yeshua advised His disciple to go further and give the creditor his cloak as well. The Torah forbids creditors from seizing a man’s cloak in a Torah court (Exodus 22:27, Deuteronomy 24:13). Yeshua advised his disciples to demonstrate their good faith by voluntarily setting aside their rights. Likewise, the Talmud says, “The Holy One, blessed be He, loves the one who does not insist on his full rights” (b.Pesachim 113b). The disciple who leaves justice in the hands of the Almighty will not be disappointed.
Yeshua told His disciples, “Whoever forces you to go one mile, go with him two” (Matthew 5:41). A disciple of Yeshua does more than is required of him. Under the tyranny of Roman occupation, Roman soldiers could force a man without Roman citizenship to carry a load for them. Few things could have been more hateful for the Jewish people than to be forced to serve the Romans like pack animals. Yeshua instructed His disciples to disarm their opponents by going an extra mile.
One ancient writer concurred with the Master’s advice in dealing with Roman impressments:
If there is a requisition and a soldier seizes your donkey, let it go. Do not resist or complain; otherwise you will be beaten first, and lose your donkey besides. (Epictetus, Dissertationes 4.1.79)
This policy for dealing with Roman requisitions and seizures sounds similar to the way that the apostles transmited Yeshua’s teaching to the Gentile disciples:
If someone forces you to go one mile, go with him two. If someone takes away what is yours, do not demand it back, for you are not even able to get it back. (Didache 1:4)
In this current age the disciple can expect to experience injustices at the hands of others, but he should not let the loss of material things perturb him, for he lives not for this current world and its things, but rather for the kingdom that is coming.