He suffered Himself to be ranked with sinners and, yet, offered Himself to be an intercessor for sinners (verse 12).
(1) It was a great aggravation of His sufferings that He was “numbered with transgressors,” that He was not only condemned as a malefactor, but executed in company with two notorious malefactors, and He in the midst, as if He had been the worst of the three, in which circumstance of His suffering, the evangelist tells us, this prophecy was fulfilled (Mark 15.27-28). Nay, the vilest malefactor of all, Barabbas, who was a traitor, a thief, and a murderer, was put in election with Him for the favor of the people, and carried it, for they would not have Jesus released, but Barabbas. In His whole life, He was numbered among the transgressors, for He was called and accounted a Sabbath-breaker, a drunkard, and a friend to publicans and sinners.
(2) It was a great commendation of His sufferings, and redounded very much to His honor that, in His sufferings, He “made intercession for the transgressors,” for those who reviled and crucified Him, for He prayed, “Father, forgive them,” thereby showing, not only that He forgave them, but that He was now doing that upon which their forgiveness, and the forgiveness of all other transgressors, were to be founded. That prayer was the language of His [death], crying, not for vengeance, but for mercy and, therein, it speaks better things than that of Abel, even for those who, with wicked hands, shed it. – Matthew Henry (1662-1714), commenting on Isaiah 53.10-12.