In our previous passage Jesus was already condemning "this generation" for acting like fickle children, but now he pushes the envelope further by pronouncing a frightening judgment upon the Israelite cities of Chorazin, Bethsaida and Capernaum. They did not believe the many miracles he had performed among them, and now there is nothing left to reveal except the wrath that their unbelief deserves.
Nothing is scarier than hearing Jesus pronounce woe upon people. Jesus is our only hope anywhere, ever. Outside of him there's nothing, no escape, no plan, no recourse, no alternative except to head straight for your doom. He is the trapdoor out of the fiery furnace, the eject button out of the nosediving plane. If Jesus condemns you, it's like hearing a life raft condemn you to a drowning.
The ancient cities of Tyre and Sidon were great centers of trade. According to Isaiah 23:3-9 Tyre was a city known for its wealth, beauty and honor, the way you'd think of a London or Paris today. Ezekiel 26-28 recounts God's judgment upon Tyre, humbling her great pride and defiling her splendor through the invasion of Nebuchadnezzar with his Babylonian army. By comparison the cities of Chorazin and Bethsaida were little podunk towns, villages really. They weren't wealthy and extravagant. They weren't great metropolises that were "playing the harlot with all kingdoms of the earth" as Isaiah said of Tyre. Yet because these cities rejected the Messiah who appeared to them in the flesh, performing signs and miracles in their midst, their sin would be judged more harshly than even the pagan decadence of Tyre and Sidon.
Capernaum receives the worst condemnation because Jesus says it will be judged more harshly than Sodom. I don’t know if Sodom's sins were objectively worse than Tyre’s and Sidon's, but certainly the mention of Sodom would have a greater emotional impact on the average Jew. To say you are worse than Sodom, now them's fightin' words. It's something someone would say along with an insult about your mother. Except here Jesus is not trying to pick a fight, he's deadly serious. The people of Capernaum evidently prided themselves on their piety. They thought they would be “exalted to heaven” when in fact they would “descend to Hades.” Jesus is just trying to get through to them about the reality of their situation.
I’ve puzzled over Jesus’ statement that if Tyre, Sidon and Sodom had seen these same miracles that he’d performed in Chorazin, Bethsaida and Capernaum, they would have repented and saved themselves from judgment. The question is, if such repentance were possible for these cities, why didn’t God give them that chance? It’s hard to say what kind of repentance Jesus is talking about here, but I imagine a repentance similar to Ninevah’s when Jonah preached to them. Ninevah saved itself from destruction for a time, but when it later returned to its wicked ways God’s judgment came swiftly (Nahum 1:14). The rule is that your judgment is harsher when you sin against greater revelation. Is it possible, then, that even though cities like Tyre, Sidon and Sodom could have repented with exposure to greater revelation, yet God chose to spare them the greater judgment that would have awaited them had they gone back like Ninevah did to their old ways? Jesus says that Judgment Day would be “more tolerable” for these cities since they didn’t sin against revelation the way Chorazin, Bethsaida and Capernaum did. It’s strange to think that Judgment Day could be tolerable for anyone, or that God might be sparing certain sinners a worse fate by withholding his revelation from them, but now we’re treading into mysteries beyond our understanding.