Setting and Overview
Matthew 22:34-40 represents the last of the Jesus responding to the challenges in the temple courts, but before he moves on to the pronouncement of woes in chapter 23, Jesus has a question himself for the Pharisees. While his question may seem independent of the challenges brought to him, they are actually closely related. The objections that had been raised to Jesus’ teachings were ultimately not about his teaching itself but rather a rejection of him. Jesus recognizes this and gets to the core of the issue: who are they expecting the Messiah to be?

Exposition
By introducing this interchange with “while the Pharisees were assembled,” Matthew connects Jesus’ question with the preceding interactions. He first asks them a rhetorical question: what do they think about the Christ? The question is too broad to answer well, but it does get them thinking, and then sets up the more specific one: whose son is he? Jesus is not asking who they expect to the immediate father of the Messiah, but rather who the significant figure is from whom he will descend. The Pharisees would have had little hesitancy in answering that question as they were very familiar with the scriptures that identified the Messiah as coming in the line of David (II Samuel 7, Isaiah 9:7, Jeremiah 23:5-6, Ezekiel 34:23-24.) So far they are correct, but their understanding doesn’t go far enough, and they have failed to consider the implication of those passages on Psalm 110.
Jesus then picks up there and asks the follow-up question of why David calls the Messiah his lord in Psalm 110:1. Jesus’ question confirms that David is the speaker of Psalm 110, which the Pharisees would have recognized as well. If David was not the speaker in that Psalm, then the speaker identifying the Davidic king as his superior would not be significant, but for someone to confess that of their descendant would be unthinkable to Jewish people. Jesus then rephrases his question to ask it from the other direction, since David does call him Lord, how could he be David’s descendant. This paradox leaves the Pharisees stumped and Jesus offers no answer at the time, nor does he explicitly claim here that he is the Messiah. That will come soon after (Matthew 26:59-66) but because of the consequences of such a proclamation in light of his greater revelation of who the Messiah truly is, Jesus waits for the right time.

Examination and Application
The Pharisees’ shortcoming in understanding the Messiah was far from a mere technicality. In failing to understand who the scriptures proclaimed him to be, they missed the direction of the Davidic kingship and what it meant for the kingdom to come. They saw the Messiah as following along in the pattern of David, but Jesus points out that David is just a shadow pointing to the greater Messiah to come, and likewise, his kingdom would be far greater as well. That is an error that is easy for us to repeat, if we look to the past as our greatest hope. Instead, God’s promises are for something far greater than we have ever known, and we can be thankful for his faithfulness.