In Matthew 19:2-4, Jesus responds to another request for a sign to conform his messianic claims with a simple yet enigmatic statement: “You cannot interpret the signs of the times.” This phrase is used (and abused) as a reference to detecting signs in contemporary history or culture that point to the nearness of the return of Christ. But that is not the meaning in Matthew 16. The signs which confirm Jesus’s claim to be the Messiah are clear (both in his teaching and his miracles), but the present generation doesn’t understand them.
The problem is the Pharisees cannot interpret the signs of the times. “Times” (καιρός) refers to a favorable time for something to happen, the right moment. In secular Greek, the word refers to a time when you might “meet with favorable luck” (BrillDAG). But in a Jewish apocalyptic context, the word refers to the time God has appointed for the coming of the Messiah and the final judgment before the restoration of the kingdom to Israel. “Jesus is referring to ‘the (last) times (set by God)’ which demand personal decision.” (Davies and Allison, Matthew, 2:582).
These signs ought to be as obvious as knowing what the weather will be like by observing sunrise or sunset. A common way to anticipate weather is “red sky at morning, sailor take warning; red sky at night, sailor’s delight.” (Leon Morris has “shepherd’s delight.” Maybe that is the Australian version of the saying?) Anyone can look at the sky and make a decent guess about what the weather is going to be like: “you don’t need a weatherman to know which way the wind blows.”
A wicked and adulterous generation looks for a sign, so Jesus says he will only give them the sign of Jonah (16:4). “This generation” refers to the people who are hearing the teaching of Jesus and witnessing the signs he has done. But they are “an evil and adulterous generation.”
An evil and adulterous generation is a fair description of Israel in the wilderness, “testing the Lord.” Not long after testing the Lord, Exodus 17, they worship the golden calf at Sinai (Exodus 32). If Israel is entering into a covenant relationship with the Lord at Sinai, then worshiping a golden calf as Yahweh while Moses is on the mountain is a spiritual adultery (on the wedding night no less!)
But the phrase “evil and adulterous generation” is also a fair description of the later kingdom of Judah under Ahaz, who swore loyalty to the Assyrians rather than to the Lord and even sacrificed his own son to a foreign god (2 Kings 16:3-4). Although Hezekiah was a good king, Judah falls quickly back into idolatry under his son Manasseh’s reign. Both Ahaz and Hezekiah are given signs to authenticate Isaiah’s predictions about the near future.
Jesus once again states the only sign this adulterous generation will get is the sign of Jonah (cf. Matt 12:40-41). As in Matthew 12:40-41, the ultimate convincing sign from heaven is the resurrection of Jesus. Is there any anticipation of Peter’s confession here? Only Matthew 16:17 calls him Simon Bar-Jonah. Most commentators do not see any foreshadowing in 16:4, Davies and Allison for example, state “there is no significant link with the bar Jonah of 16:17” (Matthew, 2:583).
In Mark 8:12, Jesus is frustrated at the lack of faith and the continued harassment from the Pharisees. Commenting on Mark 8:12, Robert Gundry says the groan may be gathering up of Jesus’ spirit before making a heavy pronouncement (Mark, 404). There are several verses which demonstrate God’s frustration with Israel in the wilderness (Ps 95:10 (LXX 94:10); Deut 32:5). In any case, Matthew omits Jesus’s (rather human) frustration with the Pharisees.
Would the Pharisees or Sadducees believe Jesus was the Messiah even if he did a miracle from heaven in response to their demand? It is unlikely the Sadducees would ever think Jesus was the Messiah since they did not think there was a Messiah coming. Jesus did not conform to the Pharisee’s expectations of what the Messiah was going to do when he did arrive. In other words, he did not act like a proper Pharisee so he cannot be the Messiah.
What are the signs of the times? Jesus’s clear demonstration of his messianic mission, even if that mission does not conform to other views in the Second Temple period. In the next section of Matthew, Jesus asks his disciples who they think he is. Will Jesus’s own disciples be like the “evil and adulterous generation” and misunderstand the signs of the times?