What does Matthew 11:22 mean?

These words from Jesus likely infuriated the Jewish religious leaders. Tyre and Sidon were pagan cities, famously used in the Old Testament as symbols of those who would suffer the wrath of God (Joel 3:4; Ezekiel 27:1–9; 28:21–23). However, Jesus has just declared that on the day of judgment, the Gentile idol-worshippers of Tyre and Sidon will be judged less harshly than the religious Israelites of Chorazin and Bathsaida.

The difference between these two pairs of cities is that one group saw Jesus perform mighty and powerful acts of healing and casting out demons. The other did not. God not only knows all that is, and all that will be, He also know all possible outcomes for all possible situations. As God, Jesus knew that if the pagans in the Gentile cities had seen Him do those things, they would have fallen to their knees in genuine repentance. By contrast, the two Jewish cities where the miracles took place refused to repent or acknowledge Jesus as the Messiah.

Many Israelites believed that simply being one of God's chosen people would be enough to secure their place in the kingdom of heaven forever (Matthew 3:9). Jesus directly contradicts that idea in this passage. Only those Israelites who repent and acknowledge Him as the Messiah, the Son of God, will avoid judgment (John 3:36).

Jesus also introduces the difficult idea that there will be levels of judgment on judgment day: the moment when Christ returns to fully establish His earthly kingdom. Some judgment for those who did not repent will be more bearable than other judgment. One reason for that difference will be the opportunity to see convincing evidence that Jesus is the Son of God.