After reading Matthew 27:38 and Matthew 27:57-6, I believe that, for convenience, the Roman soldiers likely planned to bury Jesus’ body with the two criminals that were crucified at the same time. Instead, Joseph of Arimathea came along and asked for Jesus’ body and buried Jesus in Joseph’s own tomb. This helps us understand Isaiah 53:9 in that it says Jesus “was assigned a grave with the wicked,” meaning he would be buried with criminals. It also says he was “with the rich in his death,” referring to Joseph of Arimathea, a rich man, taking care of Jesus’ body.
We can reconciles the seeming contradiction of Jesus being "assigned a grave" and that he will "prolong his days" through our knowledge that, even though Jesus died and was “assigned a grave,” He then rose from the dead, defeating death forever, which allowed him to “prolong his days” as He sits at the right hand of the Father forever.
We can reconciles the seeming contradiction of Jesus being "assigned a grave" and that he will "prolong his days" through our knowledge that, even though Jesus died and was “assigned a grave,” He then rose from the dead, defeating death forever, which allowed him to “prolong his days” as He sits at the right hand of the Father forever.