[What is] the Meaning of “Transgressors” in Luke 22:37?
Suppose we get to the title question in a moment. First, let us consider the two short queries at the end of the OP:
1.: Does the fulfillment of the prophecy lie in the fact that someone would use the sword to protect Jesus and thus be a “transgressor”?
Answer: Certainly not.
2. Did Jesus mean for His disciples to carry swords moving forward?
Answer: Almost, but let us be careful about what this means.
Shortly before Jesus was to surrender Himself to the authorities, He made the following pronouncement to the disciples as already noted in the OP:
Luke 22:35-38 NAS: “And He said to them, ‘When I sent you out without money belt and bag and sandals, you did not lack anything, did you?’ They said, ‘No, nothing.’ And He said to them, ‘But now, whoever has a money belt is to take it along, likewise also a bag, and whoever has no sword is to sell his coat and buy one. For I tell you that this which is written must be fulfilled in Me, “AND HE WAS NUMBERED WITH TRANSGRESSORS”; for that which refers to Me has its fulfillment.’ They said, ‘Lord, look, here are two swords.’ And He said to them, ‘It is enough.’”
Commentators have expressed various opinions over this rather cryptic exchange. However, these words by Christ are not to be understood literally, that He would have his disciples immediately furnish themselves with swords for battle. It’s absurd to believe that two small swords would be enough for the defense of eleven or more men.
Rather, His meaning appears to be that wherever the disciples had previously enjoyed a friendly welcome, where a door was opened to them for preaching the Gospel of Christ, they would soon face many adversaries from this point forward. Christ was about to be “numbered with transgressors” and his followers would eventually be branded with that same label.
While on this specific subject, suppose we address the primary question with dispatch. This stems from the prophecy regarding the Messiah hundreds of years earlier by Isaiah the prophet. As pointed out by other contributors:
Isaiah 53:12: "Therefore, I will allot Him a portion with the great, And He will divide the booty with the strong; Because He poured out Himself to death, And was numbered with the transgressors; Yet He Himself bore the sin of many, And interceded for the transgressors."
It should be plain enough that Christ would, at the very least, be numbered among two guilty men or "transgressors", during His Crucifixion. On the other hand, the final clause "And interceded for the transgressors" is a reference to Christ taking the penalty for all sinful men and women upon Himself. The first and second references to "transgressor" have different applications, but they are not intended to characterize the disciples and apostles of Christ.
Again, as for the disciples buying swords, resistance would emanate even from the highest domains as, for example, the Caesars (beginning with Nero), and the disciples would encounter great oppression and violence, soon after Christ’s crucifixion.
This would become so intense that they would appear to stand in need of swords to defend themselves; they must therefore seek refuge from the persecutions to come.
The phrase is expressive of the danger they would be exposed to, and of their need for protection. Theirs would represent a terribly forlorn, destitute, and afflicted condition. Indeed, they were about to witness some of this distress beginning with Christ himself as He would soon be led away to death by torture.
Verse 38 of the above passages appears to represent another instance in which the disciples were oblivious to the deeper meanings conveyed so often by Christ:
Luke 22:38: “They said, ‘Lord, look, here are two swords.’ And He said to them, ‘It is enough’” (Lk. 22:38).
Jesus was surely focused on the horrific ordeal that lay immediately before Him. Observing that they missed His point entirely, He puts the matter to rest by simply adding “It is enough,” perhaps the ancient equivalent of the modern expression, “Oh, well, whatever.”
This last comment by the Lord was simply an affirmation that the disciples misunderstood His application to their dismal future without Him. They would require every ounce of strength and determination merely for self-preservation.