Matthew 11:1  “…He departed from there to teach and to preach in their cities”
After instructing the twelve on their mission and sending them out by twos.  Commentaries vary on the meaning of their cities.  Could be the cities around Galilee or perhaps the ones that the disciples went through.  My Bible teacher said that during this time, Jesus followed behind the disciples doing follow-up preaching and teaching.  Perhaps it was similar to the idea of John the Baptist except that this was bringing the message to the people where they lived.

2  “…John had heard in prison about the works of Christ…Are You the Coming One…”
Seems odd coming from John given his announcement at Christ’s baptism.  But we must remember John was in prison so his thinking wouldn’t be completely clear.  Plus, we know he knew he was the forerunner of the Messiah, but that doesn’t mean he fully understood what Jesus was going to do.  He may have thought like others that Christ would set up His kingdom on earth then.  Now he hears that Jesus is just going around preaching and healing, not challenging the government entities.  And I’m sure John probably felt like he had been let down.  He was supposed to be the forerunner of the Messiah, but now he’s in prison.  Wasn’t the end he was expecting.

4-6  “…Go and tell John…blessed is he who is not offended because of Me”
Has always seemed a bit harsh to me, but I’m sure Jesus knew exactly what John was feeling and dealing with.  Plus we can’t see the attitude with which He said this, just the words which may seem more harsh than they were.  What Jesus described was what the prophets told would happen when the Messiah came, so He’s giving evidence.  And then He says the last part to say in essence I am the Messiah, don’t be upset if I don’t do things the way you think I should.  I think there is also the idea of trust Me, all is going according to God’s plan.

10  “…this is he of whom it is written…”
Jesus’s affirmation that John was indeed the forerunner.  If John was the forerunner, then this is further evidence that Jesus was the Messiah.

11  “…there has not risen one greater than John…he who is least in the kingdom of heaven is greater than he”
Seems a contradiction.  Obviously looking at two measurements.  Commentaries are vague.  Perhaps He is saying that by men’s standards, John is the greatest.  He knew what he was there to do, and he did it, even if he didn’t fully understand the meaning or the importance.  But anyone who believes on Christ and enters the kingdom, will come to know Christ fully.  They will understand who Christ is and what He came to do.  Perhaps He is referring to understanding salvation.  John and the other prophets had more information on the Messiah, but one who has met and accepted Him as savior will know and understand more.

12  “…the kingdom of heaven suffers violence…”
Odd section to understand.  But commentaries seem to be in agreement.  And the context makes sense.  He’s speaking directly about how the crowds have reacted to John’s message and His own about the arrival of the kingdom of God, how they’ve rushed forward to receive the news.  But this whole section is about John and the message.  The law and the prophets foretold of the Messiah.  John arrived to say that the time of the Messiah had come.  No more waiting for the Messiah, He is here.  If you’re interested in John and who he was, you realize that him being on the scene proves that the Messiah has arrived.

13  “…he is Elijah who is to come”
I’ve always had a fascination with the two witnesses mentioned in Revelation 11.  Many have said that one of them had to be Elijah since Malachi said Elijah would return before the day of the Lord.  Yet, here we see that Jesus said John had fulfilled that prophecy of Elijah.  It wasn’t Elijah himself, but someone coming in the spirit of Elijah.  I think that will be the idea in the future with the two witnesses.  The Bible doesn’t record that God ever used someone again that was prophesied, but that He raised up someone in the same spirit.  I’m sure the two witnesses will be just like Moses and Elijah, whoever they actually happen to be.

16  “…to what shall I liken this generation…”
Jesus displays their hypocrisy.  Didn’t want to hear the truth of the gospel so they found fault with John.  Yet when Jesus came preaching the same gospel and doing things opposite from John, they criticized Him as well.  Their reasons for not accepting the message didn’t hold up.

23  “…who are exalted to heaven…”
Examples of what He was just speaking about.  Capernaum had been given the privilege of seeing so much of the Messiah, like they had been exalted to Heaven.  Yet they wouldn’t repent.

27  “…Nor does anyone know the Father except the Son, and the one to whom the Son wills to reveal Him”
Know fully and completely.  The only way to God is through Christ.  He will later expound on this.  I am the way, the truth, and the life.  No one comes to the Father except by Me.  But He gives us hope in that He says He wills to reveal Him.  We can know the Father because Jesus shows Him to us by a relationship with Him.

I hope you enjoy reading and studying His word.  May it accomplish what He desires.  Please feel free to comment or post questions.  Thanks for reading!

Scripture taken from the New King James Version®. Copyright © 1982 by Thomas Nelson. Used by permission. All rights reserved.