When you read the gospels, it is obvious that crowds of people followed Jesus. For most of His ministry, He was extremely popular. But Jesus wasn't interested in being the most popular man in the world. He wanted people to follow Him, which meant, they had to repent of their sins and righteousness. As He performed miracle after miracle before them, the plan was that these miracles would show them how much He cared for them, but also that God was present before them. The miracles were meant to authenticate the message He was preaching. He wanted them to repent of their sins and follow Him.
After about a year of performing hundreds, probably even thousands, of miracles (we do not have them all recorded in the NT), Jesus responds to the indifference of the crowds. Because of their lack of repentance, Jesus pronounces woes of condemnation upon three particular cities in Northern Israel. Even with the incredible amounts of revelation they experienced, they did not change their mind about who Jesus was and they were not willing to give up their sin and righteousness to follow Him.
Jesus takes these three cities and compares them to three pagan cities. Jesus tells Chorazin, Bethsaida, and Capernaum that if the miracles they had witnessed had been performed in Tyre, Sidon, and Sodom, those cities would have repented. Sodom would still be in existence at that day (see Gen. 19). Why? Because they would not have viewed Jesus as a side show to gawk over, but they would have repented of their sins and followed Him. And then Jesus drops the bomb on them when He says that it would be more bearable for Tyre and Sidon on the Day of Judgment than for Chorazin and Bethsaida. He says that it would be more tolerable on the Day of Judgment for the land of Sodom than for Capernaum. This teaches us several important lessons concerning those who are unrepentant towards Jesus.
First, there will be a judgment. We never witness Jesus saying "if there is a judgment", but He is definitively saying that there will be one. It is appointed for men to die and then comes a judgment (Heb. 9:27).
Second, Jesus is a capable judge. He is capable because He has the knowledge to execute judgment. He knows all things actually that happen. But He also knows all things possible to happen. He knows that if those miracles would have been performed, those pagan cities would have repented (this is not Jesus using hyperbole to make a point). This is called "Contingent Knowledge."
Third, there are degrees of judgment. We are never told that those pagan cities would not be judged, just that their judgment would be more tolerable than those that had such an extensive display of revelation before them. Every indication is that Jesus means those that have more revelation will be held to a higher standard of response to Jesus. The implications for a "Christian" nation like America is devastating. We are in trouble, not because Jesus was not present in our country, but because He has been and we didn't repent.
Fourth, we only avoid judgment through repentance. There is a way to avoid the judgment that Jesus is talking about and that is to change our mind concerning Jesus and follow Him. We believe in Him (faith) and turn from our sin (repentance) and the work of Jesus is applied to our account.
Fifth, more revelation does not guarantee your repentance. I hear people say this all the time: "If only I could see some sort of miracle to prove to me that it is real, then I would repent and follow Jesus." This account of Jesus' words should scare that thought out of us. The more visual demonstrations of power didn't convince them to repent of their view of Jesus and it probably wouldn't you either.
If you want to listen to the sermon or read my notes, you can find it HERE (audio usually posted by Tuesday night).