What is the best place to start when witnessing to a Jewish person today?
The best place to start is Isaiah 53. It is a prophetic chapter concerning the work of the cross, written so that after the fact people could go back to it. For Jewish people today, it shows from their Old Testament that God had the cross in mind all along.
Les teaches that the whole chapter of Isaiah 53 is a prophetic statement concerning the work of the cross. He qualifies that Isaiah likely did not picture the crucifixion as he wrote, and Old Testament believers did not see the cross out in the future. But God had Isaiah write it so that after the fact we could go back to it. Especially for the benefit of the Jew, even today, the best place to start is Isaiah 53 and show him that out of his Old Testament, God had the work of the cross in mind all the time. Verse 4 says, "Surely he hath borne our griefs and carried our sorrows, yet we did esteem him stricken, smitten of God and afflicted when he was crucified."
Surely he hath borne our griefs, and carried our sorrows: yet we did esteem him stricken, smitten of God, and afflicted.