Summary: Why did Jesus take His disciples to Caesarea Philippi? Why go to a pagan, idolatrous city to ask His disciples the most important question of His ministry?
OPEN: I read once the story of a young black man in the ghettos. He was fortunate in that he had both of his parents, and they struggled to make ends meet. But for his birthday that year they had scraped together enough money to pay for a brand new bicycle. A few days later someone stole it. Enraged, the boy went looking for the thief and in the process of his search he encountered a policeman. The policeman asked him what he was going to do if he caught the boy who stole it and the boy said that he didn’t know.
It was obvious to the cop that if this boy ever did find the person who stole his bike, he might not only lose the bike but be beaten terribly in any fight that ensued, so he asked the boy if he would like to go the gym with him. The boy agreed and they went together to a nearby sports center where the policeman began teaching the boy how to box.
That boy was named Cassius Clay. Later he changed his name to Mohammed Ali and became one of the greatest fighters to ever enter the ring. But while Mohammed Ali was similar to many of the fighters of that time – he worked out just like they did, he boxed, and sparred and ran for miles in preparation for every fight – he had one distinguishing difference that gave him the edge whenever he put on his gloves.
Ali said, "To this day I never found my bike, but every time I got in the ring, I’d look across at my opponent and say to myself, that’s the guy who stole my bike!"
APPLY: What Ali was saying was this: He was prepared long before he stepped into the ring. He (like other prize fighters) had always prepared for the fight physically for weeks ahead of time, but what gave him his cutting edge was this: he had prepared himself mentally long before he stepped into the ring.
His disciples knew they were being training for something. Jesus had been working with them for over two years by having them follow Him wherever He went. For months, these disciples had listened Jesus as He taught. They had watched as He healed people, and fed the crowds. They had trembled as He walked upon the water and stilled the storm on the sea.
Physically, they had begun to get into shape. But, they needed something else. They needed an edge. They needed to be trained in how to think.
What we read about in Matthew 16 (quickview)  was a critical part of that part of their training. For this session Jesus takes them out of the familiar world of Galilee and Judea and into an unsettling world just across the border - into pagan territory.
He takes them to the capital of the Roman province in Judea, the seat of the governors or procurators that ruled their land, and the headquarters of the Roman troops.
Caesarea Philippi was the heart of the kind of pagan worship God had always condemned.
As Jesus stood there, He was surrounded by numerous idols and pagan that populated the region (14 temples to Baal, one to Caesar and a nearby cave was rumored to have been the birth place of the Greek God of Nature: Pan)