Matthew chapter 11

Jesus talking about John.
Verses 1-18 have John the Baptist doubting that Jesus is really the Messiah and Jesus' response to him. At this stage John is in prison and sent his disciples to ask Jesus "Are you the one who was to come, or should we expect someone else?" Back in the desert, John had preached that the Jesus was the Messiah and that He would would baptize in the Spirit and fire, casting the wicked into a furnace of fire. John doubted because he expected, like most Jews, a different kind of Messiah. Jesus was not the political or military power that was expected and John's questions arose when he heard of Jesus' deeds, which were not those of a conqueroring warrior, but those of a humble servant. Thus when John asks if he and his disciples should look for someone else, this Greek expression is in an emphatic position and the specific term emphasizes "another of a different kind". John's expectations about the Messiah's future role were right; Jesus would baptize in fire, judging the world with justice and freeing the captives. But John did not understand that Jesus had another mission to complete before the coming judgment, the mission of the atonement of sin.
Jesus then endorses John in front of the crowds listening to Him teach, in spite of John's doubts. "I tell you [he is] more than a prophet...I tell you the truth: Among those born of women there has not risen anyone greater than John the Baptist; yet he who is least in the kingdom of heaven is greater than he." When Jesus announces this, he is exalting the disciples, not minimizing John, JEsus already established that John was "more than a prophet"; he uses John for the comparison precisely because he is so significant in God's plan.

Tyre, Sidon and Sodom.
Jesus rebukes the cities of Korazin, Bethsaida and Capernaum because the people there did not repent when he travelled through them teaching and performing miracles. Jesus says that if Tyre, Sidon or even Sodom had seen such miracles even they would have repented from their wickedness. Jesus goes on to say that "it will be more bearable for Tyre and Sidon on the day of judgment than for you...it will be more bearable for Sodom on the day of judgment than for you." We know from Genesis19:1-29 that God utterly destroyed Sodom for its wickedness but what about Trye and Sidon? The Jews knew that the people of Sidon and Tyre were wicked and practiced idolitary and worshiped false gods. Jezebel, a princess from Tyre who became a consort of King Ahab and introduced to Israel, the worship of her gods.

Tyre and Sidon 101:
Tyre and Sidon were both cities founded by the Phonecians. The Phonecians were sea going merchants who had founded many powerful cities all around the Mediteranian, the most powerful of which was Carthage in northern Africa. The Phonecians lived in the promised land of Canan before the Israelites were given it by God and the people of the region called themselves the Canaani or Kenaani, the name Phoenicia became common thanks to the Greeks who called them the Phoiniki in reference to a particular Purple dye produced from secretions from the Spiny Dye-Murex, a marine snail. Sidon was older than Tyre and Tyre was actually a city founded by the people of Sidon, Isaiah refers to Tyre as the "Virgin Daughter of Sidon".
Isaiah 23 is prophecy about Tyre and its destruction. "For Tyre is destroyed and left without house or harbor." This was not accomplished until Alexander the Great and his army marched in 332 BC. Alexander was giving the peopleles he conquored 2 options
1. Assimilate into his empire.
2. Be destroyed utterly.
Tyre chose option 2. Tyre consisted of two distinct parts, a rocky fortress on the shore, called "Old Tyre", and the city, built on a small, fortified rocky island about 800 metres or half-a-mile from the shore. The people fled to their island for protection, but in responce to their 'defiance' Alexander's army spent 7 months tearing down "Old Tyre" and throwing all the rubble and materials into the ocean to build a great causeway (hence Tyre is destroyed and left without house or harbor) out to the island fortress which he breached in a matter of days. All the people were then killed or sold into slavery and disperced, the prophesey of Tyre had been fulfilled. Tyre was later rebuilt and a Church was founded there soon after the death of Stephen and the apostle Paul spent some time there as well. So the Jews would have known about the judgment Tyre faced as well, but what about Sidon?
Sidon received its name from the first-born son of Canaan, the grandson of Noah. Genesis 9:18-29 has a curse put on the decendants of Canan by Noah to ever be the lowliest of slaves to his brothers. Hence the history of Sidon has been to never be an independant state for too long. Sidon has had many conquerors: Philistines; Assyrians; Babylonians; Egyptians; Greeks and finally Romans in the years before Jesus. On December 4, 1110 Sidon was sacked in the First Crusade. During the Crusades it was sacked several times: it was finally destroyed by the Saracens in 1249. It became the centre of the Lordship of Sidon, an important seigneury in the Kingdom of Jerusalem. In 1260 it was again destroyed by the Mongols. The remains of the original walls are still visible.
After Sidon came under Ottoman Turkish rule in the seventeenth century, it regained a great deal of its earlier commercial importance. The Egyptians, assisted by England and France, captured and held the city in the nineteenth century. During WWI, the British took Sidon; after the war it became part of the French Protectorate, (a state protected and/or dominated by a foreign power) in the Eastern Mediterranean.
So even if we miss the references, the Jews listening to Jesus would not have. Tyre and Sidon were two cities in Canan whos people were destroyed and/or made slaves. By men instead of God, but still as part of God's judgment according to an Old Testament prophesey and a curse.

In effect, when Jesus says to the unrepentant cities "it will be more bearable for Tyre and Sidon on the day of judgment than for you...it will be more bearable for Sodom on the day of judgment than for you." He is really saying "Being unrepentant before the Day of Judgment is goibng to be far worse than being Destroyed by fire from heaven, put to the sword or sold into slavery."
Rest for the weary. (Matthew 11:25-30)
Just as Israel was wrongly secure in its status before God as above the Gentiles, so the wise and powerful failed to recognize that God favored the children, the meek. Jesus does not call the mighty or wise to follow him, but the humble laden with heavy burdens, the weary, like Israel in exile, who hope in God alone. They will find Jesus' yoke light because he is a Master who will care for them. Jesus' yoke is not lighter because he demands less, but because he bears more of the load with us. In contrast to unconcerned religious teachers who prided themselves on their own position, Jesus was going to lay down his life for the sheep.