“A second detail recorded by both Matthew and Mark is that Jesus was crucified between two other criminals, one on His right and one on His left. The same fact is recorded by Luke though with slightly different wording. All three accounts stress the word ‘with’; they were crucified along with Jesus.
The Scripture referred to is Isaiah 53:12, and this verse is certainly quoted by Jesus Himself just before He goes to Gethsemane: ‘It is written, ‘And he was numbered with the transgressors’; and I tell you that this must be fulfilled in Me. Yes, what is written about Me is reaching its fulfillment’ (Luke 22:37).
There is no doubt about the authenticity of this passage, nor about the authenticity of the original words of Isaiah, and we must take them with complete seriousness. The truth they point to, Jesus’ solidarity with sinners, did not begin at the cross; it had been a fact throughout His life.
He had made Himself notorious as the friend of tax collectors and sinners and repeatedly allowed Himself to be compromised by associating with people of dubious reputation. But here at the cross the solidarity climaxes.
He is not merely among His two co-accused. He is together with them; and He is together with them specifically in their character as transgressors and criminals.
The full force of this is brought out in the original wording of Isaiah: He was numbered with the transgressors ‘for he bore the sins of many.’ It is not a matter of mere association or even, ultimately, of mere solidarity, as if He were just taking the position of a sinless one forced to endure the company of sinners.
He identifies completely. He lets Himself be reckoned as a sinner, and dealt with as a sinner; and not only by men, but by God. He has come to redeem sinners, but the way He will redeem them is by taking their sins as His own and becoming accursed in their place (Gal. 3:13).
By hanging Him in the middle, wrote Calvin, ‘they gave Him first place as though He were the thieves’ leader.’ Luther, ever more graphic, put it even more strongly: ‘He bore the person of a sinner and of a thief– and not of one but of all sinners and thieves… And all the prophets saw this, that Christ was to become the greatest thief, murderer, adulterer, robber, desecrator, blasphemer, etc., that has ever been anywhere in the world.’
Here, on the cross, He not only bears, but is (2 Cor. 5:21) the sin of the world; and so here, in solemn divine equity, the sword falls.”
–Donald Macleod, Christ Crucified: Understanding the Atonement (Downers Grove, IL: InterVarsity Press, 2014), 38-39.