Why did Jesus keep some in the dark by using parables?

Lord Jesus did that only what Father the God told to do.John 5:19. Lord Jesus wants the people to have understand on truth through ONLY the revelation of Father instead faith coming from miracle.

Faith should be coming from Father's revelation. 2 Corinthians 5:6, John 14:9.

Lord Jesus was well aware of His Father's will and did it accordingly. John 5.19. Father will is that people must understand the truth ONLY through His Spiritual revelation in their heart instead of understand the truth through great miracles or talking plainly. John 6:44,65. To understand the truth we must have grace of Father within us john 6:37 otherwise noone come to Lord Jesus or understand the truth. Luke 24:45, Matthew 16:17 The truth is Jesus Christ.

Thanks to Mojo, Bye and Narnian.

Even though the answers by both Narnian and Mojo, completely and accurately answer your question. I felt it necessary to add some more elaboration to what they said.

We must take into account the fact that we now understand that the Messiah referred to Jesus Christ as the son of God. Before Jesus death and resurrection, the Jewish nation was expecting a military type leader who would oust the Roman government and Israel would again become the great nation that it had been under both David and Solomon. A large portion of the Jewish population still expects that military leader who will make Israel a great nation as it once was.

let's take into consideration some of the things which Jesus said and compare that to the expectations of the Jewish people at the time.

Matthew 5:17 and 18 KJV Think not that I am come to destroy the law, or the prophets: I am not come to destroy, but to fulfil. For verily I say unto you, Till heaven and earth pass, one jot or one tittle shall in no wise pass from the law, till all be fulfilled.

And Jesus said this right after he had finished giving the sermon on the Mount. Today we know and understand what this meant because we know that Jesus died on the cross and rose on the third day. However, the people listening to this sermon on the Mount did not have this knowledge so how do you expect that they might have received what Jesus said?

Remember that Jesus told his disciples, that the common people were not given to understand what he was saying but that they were. Consider this verse:

Matthew 16:17 KJV And Jesus answered and said unto him, Blessed art thou, Simon Barjona: for flesh and blood hath not revealed it unto thee, but my Father which is in heaven.

We now have the New Testament with which to help us understand the Old Testament but it was not so for the people of Jesus day. All they had was essentially the Pentateuch, (or the writings of Moses) and the prophets. Today we understand Daniel chapter 7 because of our knowledge of Jesus Christ and because of the explanations in the book of Revelation, how hard would it be to understand Daniel chapter 7 if we did not have those to go by.

Psalm 78 is cross-referenced by Matthew 13:35 (in my study Bible).

My people, hear my teaching; listen to the words of my mouth.

2 I will open my mouth with a parable; I will utter hidden things, things from of old—

3 things we have heard and known, things our ancestors have told us.

4 We will not hide them from their descendants; we will tell the next generation the praiseworthy deeds of the Lord, his power, and the wonders he has done.

5 He decreed statutes for Jacob and established the law in Israel, which he commanded our ancestors to teach their children,

6 so the next generation would know them, even the children yet to be born, and they in turn would tell their children.

7 Then they would put their trust in God and would not forget his deeds but would keep his commands.

8 They would not be like their ancestors— a stubborn and rebellious generation, whose hearts were not loyal to God, whose spirits were not faithful to him.

Note the ironic inversion. The people to whom the Psalmist is addressing his poem were supposed to teach their children God's ways using parables to make the sense clear, so that their children would not be proud and rebellious like their ancestors. They failed. Jesus is now teaching adults who act like rebellious children, whose own parents failed to teach them correctly, using parables that they cannot understand.

In doing this, Jesus is obeying what is prophesied in Scripture. It said to teach children using parables, and so he did. What the people found difficult to swallow was that Jesus was reinterpreting all the Old Testament as being one big parable - the entire sacrificial system was merely a parable about the coming Messiah who would be the lamb slain for their sins. Not only did parables have hidden meanings that they could not follow, but the certainties of how to interpret their history and laws were being called into question.

In the end, Jesus must use parables, because nothing about God can be understood without some sort of analogy, he is not like us.

I perceive a few reasons why Christ taught in parables:

1. As someone elsewhere said, the people didn't understand that the primary mission of the Messiah was to "save people from their sins." They had been taught by the scribes and Pharisees that when the Messiah would come, He would not only deliver them from all their enemies but would also set up a physical kingdom on earth. No truer were the words of Christ than when He rebuked the teachers of the law for "shutting up heaven" and "taking away the keys (of knowledge)" so that the people would be blind as they were towards the Messiah.

2. Since the people were already blinded by the labyrinth of false teaching, Christ had to get them to ask questions about God's kingdom (which is one of the signs of a heart that loves learning and wants to understand the things of God.) That's why Christ's teachings are so important; they weren't just nice stories but were tools in aiding people and helping them think about God's kingdom. However, in teaching from the parables, Christ also demonstrated what His own mission was and how it would work out in the long term.

3. The religious leaders didn't like that way of teaching because it got people to question where their authority came from which is why they tried so many different times to discredit Jesus and make him look bad to everyone. What the people didn't understand was that Christ's mission was TWO-FOLD; to save them from their sins and THEN at His SECOND COMING set up His physical kingdom on earth. The scribes and pharisees however loved their money and their material gain more than the things of God so they started teaching the people that when the Messiah would come, He would usher in a brand new political and religious kingdom not unlike Solomon's or King David's

On a side note, it is very interesting to note that God had warned the children of Israel about taking a king when they had demanded one from Prophet Samuel.

Wisdom is for the Humble

Psalm 138:6 (NASB)
For though the LORD is exalted, Yet He regards the lowly, But the haughty He knows from afar.

Proverbs 3:34 (NASB)
Though He scoffs at the scoffers, Yet He gives grace to the afflicted.
(quoted in James 4:6 and 1 Peter 5:5)

Matthew 11:24-30 (NASB)
At that time Jesus said, "I praise You, Father, Lord of heaven and earth, that You have hidden these things from the wise and intelligent and have revealed them to infants."

God does not seem to be especially disposed to the intelligent (any more than he is to the athletic, beautiful, charismatic, etc.), and so we often see a theme in the Bible that wisdom is not something to be attained without first humbling ourselves before God who gives wisdom. It seems a reasonable implication that wisdom is not something that can be wholly attained by study or genius apart from the desire to understand.

Since God desires for people willing to choose to seek him, he frequently gives understanding only after obedience. It is only when we demonstrate (to ourselves, primarily) with our actions that we trust him that we begin to understand.

A similar example of God doing this is found in Isaiah 6.

Isaiah 6:9-10 (NASB)
He said, "Go, and tell this people : 'Keep on listening, but do not perceive ; Keep on looking, but do not understand.' "Render the hearts of this people insensitive, Their ears dull, And their eyes dim, Otherwise they might see with their eyes, Hear with their ears, Understand with their hearts, And return and be healed."

Believing is Seeing

Why hide understanding from people? In the US (and probably elsewhere), we have a proverb: "Seeing is believing." In God's eyes, it appears that the illogical converse is more true: "Believing is seeing."