It isn't too uncommon to hear in our circles that some preaching on OT passages falls short, because it contains nothing that a Jew might not agree with.
Here's the way Trevin Wax put it. He says a Christian preacher should ask himself: "As I preach from the Old Testament, is there anything in my sermon that a faithful Jew could not affirm?" Trevin then adds this comment:
The intent clearly is the laudable aim of being true to passages such as Luke 24:27 and 44, among others. Insofar as Trevin's point is that a Christian sermon should not be mistakable for mere travelogue, history lecture, or moral pep-talk, I'd unreservedly agree.
However, the question as phrased was, "Is there anything in my sermon that a faithful Jew could not affirm?"
To that, my own response is, "Goodness, I hope not!"
Trevin said faithful Jew. I take that to mean believing Jew. That being the case, why would I want to break faith with a faithful Jew? Why would I want to imply to a believing Jew that the God's words to Him were not perspicuous, were coy, or perhaps were even borderline deceptive?
Was this Jesus' approach? Hardly. To pick just one very telling interchange, hear our Lord's words to his opponents:
You search the Scriptures because you think that in them you have eternal life; and it is they that bear witness about me, 40 yet you refuse to come to me that you may have life. 41 I do not receive glory from people. 42 But I know that you do not have the love of God within you. 43 I have come in my Father’s name, and you do not receive me. If another comes in his own name, you will receive him. 44 How can you believe, when you receive glory from one another and do not seek the glory that comes from the only God? 45 Do not think that I will accuse you to the Father. There is one who accuses you: Moses, on whom you have set your hope. 46 For if you believed Moses, you would believe me; for he wrote of me. 47 But if you do not believe his writings, how will you believe my words?” (John 5:39–47)A faithful, believing Jew, Jesus says, would have been led by Moses' writings to faith in Him. In fact, He said that Moses himself would accuse anyone who did not follow that progression. How could Moses accuse his readers for not finding a meaning in the text that was not, in fact, in the text? How could he accuse them for not understanding what he himself would never have understood? (This argument is made, and this hermeneutic developed, more fully by Michael Rydelnik. See also the specific application to Proverbs in Appendix Four of God's Wisdom in Proverbs.)
If Moses' writings did not actually point to Christ, the Lawgiver must instead rise and say "You know, I can't really blame you for not seeing Christ from what I wrote. I didn't see Him, myself!" But this is not what Christ claims, is it?
In my preaching Christ from OT Scriptures, I must be true to the OT Scriptures. I will be able to point to fulfillments which the original authors and readers could not know (because they had not yet happened). But those fulfillments will be in line with the words of the text — or, as we've often said in response to postmodernism, the text is plastic, the text no longer is the control, the text itself has no authority, and the author is dead.
Which, I'd argue, no Christian should want to affirm.
This question can lead (and, in many cases as we all know, has led) to reading in meaning not resident in the text, as well as minimizing the content of the text. The challenge — and it is a challenge — is to remain true to the text as given, in context, and show in what ways it points forward to Christ.
Perhaps what Trevin meant was, "Is there anything in my sermon that an apostate Jew could not affirm?"
That would make for a more useful question to ask myself.