In my neighborhood, there are almost thirty Jewish synagogues. These congregations include Reformed, Orthodox, and Hasidic Judaism. And, of course, our city is full of secular Jews who have long left any traditional form of their faith. So, on any given Sunday, there is a possibility of having a small handful of folks who identify themselves with any of the above Jewish traditions present in our church service.
Just as having divorced individuals present will affect the way you preach a sermon on marriage, having Jews in your service will affect the way you preach the gospel. In fact, it's likely to make it more biblical.
First of all, like those offended by Paul or Peter's preaching, you will likely see people offended when you use their Scriptures to show that Jesus is the Messiah and true King of Israel.
I don't know how you get around that, but the Apostles seemed to expect it, so we should probably expect it as well. After all, the gospel is offensive. However, the Apostles give us examples that keep us from being more offensive than the gospel and help us make explicit what is the offense of the gospel.
So, here are several points to help us in preaching to Jews the gospel from the Old Testament:
Know the Old Testament Well
There is no substitute for knowing the Old Testament. There are no shortcuts here either. In order to understand how the Apostles in the New Testament preached and how we should preach today, we must know the Old Testament. We need to know not only the stories but also how they organically relate to each other. What is the storyline of the Old Testament? What are the themes that run throughout the storyline (for example, Son of God, covenant, God's presence, land, and so on)? Once you begin to see these things more clearly, you'll also see the many unresolved tensions in the Old Testament that are just begging to be resolved in Jesus Christ.
Follow Closely and Learn from the Apostles' Examples in Acts
Luke's account of the early Apostolic ministry is hugely important. It's the only substantial account of Apostolic sermons in which Christ is explicitly preached from the Old Testament. Here are three examples:
Peter, after Pentecost, argued that David must have been talking about someone greater than himself when he said in Psalm 16:10, "You will not . . . let your holy one see corruption" (see Acts 2:25–40).
Stephen, in front of the Sanhedrin, argued that throughout the history of Israel, the people had followed the pattern of rejecting God when He condescended toward, spoke to, and even dwelt with them. Their rejection of His Son was no different (Acts 7:1–53).
Paul, in Antioch, showed that not only was Jesus an offspring of David, but His resurrection fulfilled all the hopes of David's kingly line promised by God (Acts 13:16–41).
These men weren't using fanciful hermeneutical magic tricks to make Jesus appear wherever they wanted, but they showed that Jesus fulfilled the hopes and relieved the tensions of the Old Testament, which is the next point.
Show How Jesus Fulfills the Hopes and Relieves the Tensions of the Old Testament
The gospel of Jesus Christ fulfills every hope and relieves every tension in the Old Testament: the hope of the forgiveness of sins and the tensions of an inadequate priesthood; the hope of rest and the tensions of a people never at peace with their enemies; the promise of God dwelling with His people and the tension of a temple-less people.
For example, remember God's promise to David that he would always have a son on the throne. God said to David in 2 Samuel 7:14: "I will be a father to him, and he shall be to me a son."
As D. A. Carson has put it, either David would have one son on the throne, who would have another son on the throne, and on and on and on, forever and ever, amen; or, he would have one special Son, who would remain on the throne forever.
If we look at this line of David, we sadly see that his descendants rebelled against God, following other nations and trusting in their false idols. (This was even true of Solomon, the son to whom David first passed on the kingship.) Soon after, the nations collapsed in on Israel, taking them off into slavery and exile, and no king sat on the throne. The promises of God looked to be all but broken. If you read the end of the Old Testament, you can almost hear the laboring cry: "We need a son."
Of course, the good news is that in Luke 3:22, we find one of whom God says, "You are my beloved Son; with you I am well pleased." Actually, God says the same thing about anyone who submits to His reign and enters into His kingdom.
Though offensive, for Jews—and for all of us—that's the best news in the world.