Matthew 16 Commentary

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Charts from Jensen's Survey of the NT - used by permission
Another Chart from Swindoll

BY MATTHEW (shaded area)

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Source: Ryrie Study Bible

Matthew 16:1  The Pharisees and Sadducees came up, and testing Jesus, they asked Him to show them a sign from heaven

  • Pharisees: Mt 5:20 9:11 12:14 15:1 22:15,34 23:2 27:62 
  • Sadducees: Mt 16:6,11 3:7,8 22:23 Mk 12:18 Lu 20:27 Ac 4:1 5:17 23:6-8 
  • tempting: Mt 19:3 22:18,35 Mk 10:2 12:15 Lu 10:25 11:16,53,54 20:23  Joh 8:6 
  • a sign: Mt 12:38,39 Mk 8:11-13 Lu 11:16,29,30 12:54-56 Joh 6:30,31 1Co 1:22 

Related Passages:

John 2:18+  The Jews then said to Him, “What sign do You show us as your authority for doing these things?”

Matthew 12:38-42+ Then some of the scribes and Pharisees said to Him, “Teacher, we want to see a sign from You.” 39 But He answered and said to them, “An evil and adulterous generation craves for a sign; and yet no sign will be given to it but the sign of Jonah the prophet; 40 for just as JONAH WAS THREE DAYS AND THREE NIGHTS IN THE BELLY OF THE SEA MONSTER, so will the Son of Man be three days and three nights in the heart of the earth. 41 “The men of Nineveh will stand up with this generation at the judgment, and will condemn it because they repented at the preaching of Jonah; and behold, something greater than Jonah is here. 42“ The Queen of the South will rise up with this generation at the judgment and will condemn it, because she came from the ends of the earth to hear the wisdom of Solomon; and behold, something greater than Solomon is here. 

Luke 11:16+  Others, to test Him, were demanding of Him a sign from heaven.

John 4:48+ So Jesus said to him, “Unless you people see signs and wonders, you simply will not believe.”

1 Corinthians 1:22   For indeed Jews ask for signs and Greeks search for wisdom;

The "Pharisees (pharisaios) and Sadducees (saddoukaios) came up - This "despicable duo" is significant because these two groups were normally hostile to one another and yet here they see Jesus as their common "enemy" and thus become "friends" (see note on "enemy of my enemy").  This is the first time these natural enemies had joined forces to attack Jesus. 

Broadus Here, as in Matthew 3:7, there is but one article (literally, the Pharisees and Sadducees), presenting the Sadducees as accompanying the Pharisees....The Sadducees appear only three times in the Gospel history; (1) witnessing the baptism of John, Matthew 8:7, (2) tempting Jesus here, (3) tempting him, not at the same time with the Pharisees, but separately, in Matthew 22:23. (Mark 12:18 Luke 20:27) They are also spoken of by Jesus in Matthew 16:6,11 f., and are mentioned nowhere else in the Gospels.  Only a few weeks before, and not more than a few miles away, Jesus had severely censured the Pharisees as hypocrites and violators of God's word (Matthew 15:6,7) and had spoken of them as blind guides of the people, unworthy of notice. Yet the dissembled hostility here indicated was not first awakened by that censure, for they had already accused him of being in league with Beelzebub. (Matthew 12:24) Some critics think it incredible that Sadducees should have come with Pharisees. But they were temporarily united by common hostility to Jesus. Comp. Herod and Pilate, Luke 23:12, and Psalm 2:2. (Commentary on the Gospel of Matthew.)

And testing Jesus - Matthew states the clear purpose of these serpents seeking a sign! It was to test (present tense - continually) Jesus. Their heart was evil and their motives were corrupt for they were not seeking a sign so that they might believe in Him. Like father, like son. These evil men were like their father Satan (Jn 8:44) as Matthew had described when "Jesus was led up by the Spirit into the wilderness to be tempted (peirazo) by the devil." (Mt 4:1+) The devil tested Jesus in an attempt to get Him to sin. 

Broadus on testing Jesus -  (cf. on Mt 4:1,7), with the hope that he will not stand the test, will not be able to show the sign; comp. Matthew 19:3, Mt 22:18,35. The Scribes and Pharisees had asked a sign from him in Matthew 12:38, and were refused. Now the Pharisees and Sadducees make a similar demand specifically for a 'sign from heaven' (so also Mark 8:11), and get (Matthew 16:4) exactly the same refusal as before. (Matthew 12:39) They might be thinking of such signs as when Moses gave bread from heaven, (Ps 78:23-25.; John 6:30-33) Joshua made the sun and moon stand still (Josh 10:12,13), Samuel brought thunder and rain in time of harvest (1 Sa 12:17, 18), Elijah repeatedly called down fire from heaven (2 Kings 1:10-12), and at Isaiah' s word the shadow went back on the dial (Isaiah 38:8); comp. Joel 2:30ff. Origen conjectures that they regarded signs on earth as wrought in Beelzebul. (Matthew 12:24) Probably some Jews really expected celestial signs of Messiah's approach; but the present request was made from bad motives. Jesus promised "great signs from heaven" in connection with his second coming, (Matthew 24:29,30.; Luke 21:11,25; cp. Rev. 15:1) and predicted that the false Christs would show great signs. (Matthew 24:24) (Commentary on the Gospel of Matthew) 

Testing (3985)(peirazo from peira = test from peíro = pierce to test durability of things) is a morally neutral word simply meaning “to test”. Whether the test is for a good (as it proved to be in Heb 11:17) or evil depends on the intent of the one giving the test and also on the response of the one tested. (See related words dokimazo;  peirasmos

Mark alluded to the testing by the religious leaders "Then they sent some of the Pharisees and Herodians to Him in order to trap Him in a statement. They came and said to Him, “Teacher, we know that You are truthful and defer to no one; for You are not partial to any, but teach the way of God in truth. Is it lawful to pay a poll-tax to Caesar, or not? “Shall we pay or shall we not pay?” But He, knowing their hypocrisy, said to them, “Why are you testing Me? Bring Me a denarius to look at.” (Mark 12:13-15+)

They asked Him to show them a sign from heaven - He had performed many "signs" on earth that only stiffened their unbelief. Even if He performed a miracle from heaven they would not believe in Him! The fascinating thing is that Jesus Himself was the ultimate sign for He was God Who had come from Heaven and they were blinded to that incredible truth!  As Luke had recorded at Jesus' birth "Simeon blessed them and said to Mary His mother, “Behold, this Child is appointed for the fall and rise of many in Israel, and for a sign to be opposed" (Lk 2:34+)

MacArthur explains "Popular Jewish superstition held that demons could perform earthly miracles but that only God could perform heavenly ones. From heaven indicates the desire to see a miraculous sign in the sky. The Pharisees and Sadducees demanded a miracle they thought was beyond Jesus, hoping to prove that His power, and therefore His message, were not divine. He would be publicly discredited, and they would be vindicated...As Abraham said of the brothers in the story of the rich man and Lazarus, "If they do not listen to Moses and the Prophets, neither will they be persuaded if someone rises from the dead" (Luke 16:31). Like Pharaoh before Moses, the more they saw God's power demonstrated, the more they hardened their hearts against Him (Ex. 7-11). Heavenly signs would come in the future (Matt. 24:29-30; Luke 21:11, 25; Acts 2:19; Rev. 15:1), but they would signal the very end. (MacArthur New Testament Commentary – Matthew)

The religious leaders were like Voltaire who said "Even if a miracle should be wrought in the open marketplace before a thousand sober witnesses, I would rather mistrust my senses than admit a miracle." 

Sign (4592)(semeion akin to semaino = to give a sign; sema = a sign) is a distinguishing mark or symbol that carries a special meaning or like a simple sign points to something else. In Scripture when semeion used of God's miraculous works (that which is contrary to the usual course of nature) it points to spiritual truth. A sign directs attention away from its unusual nature to the meaning and the significance it points to. It speaks of outward compelling proof of divine authority.  Twice in Matthew Jesus answered the Jews request for signs declaring "An evil and adulterous generation craves for a sign; and yet no sign will be given to it but the sign of Jonah the prophet." (Mt 12:39, Mt 16:4) He was referring of course to His resurrection as the sign of Jonah. In the uses of semeion by His disciples in Matthew 24, Mark 13 and Luke 21 there of course was no rebuke for they were not asking out of a heart of unbelief but of belief. Ancient peoples often viewed signs in the sky, such as lightning or eclipses, as omens of terrible things to come (Mt. 16:3).

Wiersbe says that a sign is "Something that points beyond itself to something greater. It was not enough for people to believe in Jesus' works; they had to believe in Him and in the Father who sent Him (John 5:14-24). This explains why Jesus often added a sermon to the miracle and in that sermon interpreted the sign. In John 5, the healing of the paralytic on the Sabbath opened the way for a message on His deity, "the Lord of the Sabbath." The feeding of the 5,000 (John 6) led naturally into a sermon on the Bread of Life." (BEC)

Trench on sign - "It is involved and declared in the very word that the prime object and end of the miracle is to lead us to something out of and beyond itself: that, so to speak, it is a kind of finger-post of God, pointing for us to this: valuable, not so much for what it is, as for what it indicates of the grace and power of the doer, or of his immediate connection with a higher spiritual world"

Related Resource:

Matthew 16:2  But He replied to them, "When it is evening, you say, 'It will be fair weather, for the sky is red.'

  • When: Lu 12:54-56 

But He replied to them, "When it is evening, you say, 'It will be fair weather, for the sky is red.' - This recalls a common saying ""Red sky at night is the shepherd's delight; Red sky in the morning is the shepherd's warning,"

Believer's Study Bible - Rebuke comes to the Pharisees and Sadducees for their ability to examine the meteorological evidence and predict the weather, while failing to read the evident signs of the hour and comprehend the unfolding of God's plan and program.

MacArthur Those sayings correspond to the age-old mariner's ditty, "Red sky at night, sailor's delight. Red sky in the morning, sailor's warning." From many years of observation men learned that a red sky in the evening is usually followed by good weather, whereas a red sky in the morning is often followed by a storm. The religious leaders who confronted Jesus accepted the reliability of that folk meteorology without question. (MNTC-Mt)

Matthew 16:3 "And in the morning, 'There will be a storm today, for the sky is red and threatening.' Do you know how to discern the appearance of the sky, but cannot discern the signs of the times?

  • O ye: Mt 7:5 15:7 22:18 23:13 Lu 11:44 13:15 
  • the signs: Mt 4:23 11:5 1Ch 12:32 

And in the morning, 'There will be a storm today, for the sky is red and threatening.' - As noted above, this was an common saying of the day.

Do you know how to discern the appearance of the sky - The religious leaders knew these weather "signs" 

MacArthur - Their method of predicting the weather by looking to the color of the sky was primitive and crude. Yet, ironically, they were better meteorologists than theologians. They could recognize a coming storm from something as subtle as a ruddy morning hue, but they failed to recognize the coming of the Messiah in spite of the abundant evidence that was right in front of them. (MNTC- Mark)

but cannot discern the signs of the times? This alludes to the various indications the the Messianic age was at hand, including the fulfilment of Messianic prophecies, as well as the miracles wrought by Jesus and his followers, for such miracles were considered to be a sign of the Messianic Age (see Isaiah 35:5-6)..These spiritually blind religious leaders could make a weather forecast but could not make a "Messiah forecast!" Sadly they knew more about the weather than they did about the God Who caused the weather! Blind guides Jesus called them! Their "prophetic wrist watches" were broken and they had no clue that the signs of the times clearly showed it was the time fo the Messiah! Are not these ancient religious leaders still in our midst, men like Stephen Hawking who was brilliant and wrote a book by the pretentious title "A Brief History of Time." Indeed, our modern world has many who can predict various things but fall short of understanding God's plan for the ages which is consummated in His Son Jesus Christ! 

MacArthur adds "They were better weathermen than biblical scholars (cf. Luke 12:54-56). They were "blind guides of the blind" (Matt. 15:14). In Matthew 23, Jesus labeled them blind guides (Mt 23:16, 24) and blind fools (Mt 23:17)." (Ibid)

MacArthur commenting on Jesus words on signs in Mt 24:3, 6, 7, 11, 12 wrote "signs that Jesus will return abound in our day. No period of history has experienced more wars or been so preoccupied with the prospect of war as our own. With unprecedented surpluses of food in some parts of the world, other parts still experience devastating famines. Cults and false religions of every sort are proliferating even in countries that have been nominally Christian for hundreds of years. The spirit of lawlessness and self-will is rampant....All of those signs that mark the end times are characteristic of our day. There can be no doubt that we live near the end of the age, and the concern of believers should be for what the Bible says rather than for what men say and for what God is doing rather than for what men are doing. (Ibid)

THOUGHT - Do you see the manifold signs around us today (I am writing in September, 2020)? Are you preparing to meet your God (Amos 4:12)? Do you know the Son of God by grace through faith so that you will not need to shrink back in shame at His coming? Are you looking for the Blessed Hope, so you are motivated to live for Him? (Titus 2:13+) John writes that "everyone who has this hope fixed on Him purifies himself, just as He is pure." (1 Jn 3:3+) His return is Imminent so let us each, enabled by His Spirit, diligently seek to Redeem the Time for the days are evil (Eph 5:16+). Now is the time to "store up for yourselves treasures in heaven, where neither moth nor rust destroys, and where thieves do not break in or steal (Mt 6:20+)

Matthew 16:4  "An evil and adulterous generation seeks after a sign; and a sign will not be given it, except the sign of Jonah." And He left them and went away.

  • evil: Mt 12:39,40 Mk 8:12,38 Ac 2:40 
  • except: Jon 1:17 Lu 11:29,30 
  • And he: Mt 15:14 Ge 6:3 Ho 4:17 9:12 Mk 5:17,18 Ac 18:6 


An evil and adulterous generation seeks after a sign - In the parallel account in Mark 8:11 we read that "The Pharisees came out and began to argue with Him, seeking from Him a sign from heaven, to test Him." Here Jesus "defines" these men seeking after a sign as "evil" and "adulterous." Jesus used this phrase evil and adulterous generation to describe the Pharisees in Mt 12:39 in their initial request for a sign. This description recalls the words of  Deuteronomy 32:5, 20.

5 “They have acted corruptly toward Him, They are not His children, because of their defect; But are a perverse and crooked generation. 
20 “Then He said, ‘I will hide My face from them, I will see what their end shall be; For they are a perverse generation, Sons in whom is no faithfulness. 

Evil (wicked, bad) (4190)(poneros from poneo = work or toil, cf  poneria) means evil, malignant character, pernicious and denotes a determined, aggressive, and fervent evil that actively opposes what is good. Poneros is not just bad in character (like kakos - see below), but bad in effect (injurious), evil in active opposition to good.  Poneros used to describe Satan (ho poneros = "Evil one"), the god of this age, who is corrupting man and dragging him to destruction. This denotes someone who is not content in being corrupt themselves. They seek to corrupt others and draw them into the same destruction!

Adulterous (3428)(moichalis related to moichos = "married and impure", literally adulterer, "unlawful" lover, 1Co 6:9, He 13:4, Lk 18:11; Lxx = Job 24:15, Pr 6:32) pertains to being unfaithful to one to whom one should remain faithful and here is used literally of a wife who does not remain faithful to her husband. Figuratively moichalis is used to describe one who is unfaithful (in Lxx of His "wife" Israel [cp this idea in the OT [but these passages do not use moichalis] Je 2:2, Je 3:14, Je 3:14KJV, Je 3:14NIV, Je 31:32, Isa 54:5, Hos 2:16YLT] Ezek 16:38, 23:45) toward God even as an adulteress is unfaithful toward her husband (Mt 12:39, 16:4, Mk 8:38 - observe how Jesus links adulterous with evil and sinful and the serious consequences for this state of unfaithfulness!)

MacArthur explains the concept of "adulterous generation" - The scribes and Pharisees (Mt 12:24, 38) represented the nation of Israel, which had wandered far from God’s Word and fellowship and which had become enmeshed in the superficial, self-righteous, and legalistic religion those leaders epitomized. The unbelieving Jews were not only physically and mentally but spiritually adulterous because they had breached the vows of their unique covenant relationship with God, a relationship the Old Testament frequently speaks of in terms of marriage (see Ps. 73:27; Isa. 50:1; Jer. 3:6–10; 13:27; Hos. 9:1). Their idolatry, immorality, unbiblical traditions, and hardness of heart marked them as an evil people. During the Babylonian captivity Jews had forsaken formal idolatry, in the sense of worshiping physical objects carved from wood, stone, or metal. But in its place they erected idols of man-made tradition in which they trusted and put their hope. They had abandoned the Canaanite gods for ones of their own making and in doing so were just as much in rebellion against the true God as when they offered sacrifices to Baal or Molech. A Jew who faithfully served God under the covenant given to Moses would accept His Son when He came, because anyone rightly related to the Father could not fail to recognize the Son-just as did the godly Simeon and Anna (Luke 2:25–38), John the Baptist (Matt. 3:14), and the twelve disciples, except Judas (Carl Bloch's famous painting of Judas retiring from the Last Supper)(Mt 4:20–22; Mark 3:13; Luke 5:27–28; John 1:41, 49). Because they knew the Father, they knew the Son and did not need a sign to verify His identity. (MacArthur NT Commentary)

And a sign will not be given it, except the sign of Jonah (cf Mt 12:39, 40+) - So they would receive a "sign" and it would be His last sign to them, for it was the greatest sign, His resurrection from the dead, the sign that must be believed in order to enter the Kingdom of God, which these foolish men futilely sought by works and not by faith! "Sadly, even that (SIGN) would be knowingly rejected by the religious leaders, who bribed the Roman soldiers, instructing them to spread lies about what actually took place at the tomb (cf. Matt. 28:11–15)." (MacArthur)

Let be be understood,
unless one is abandoned to God,
he will be abandoned by God!

And He left them and went away - The word left is kataleipo meant He left them behind using a verb which also carried the idea of forsaking or abandoning (2 Pet. 2:15). See the diagram in Mt 16:13 which depicts this time as a critical transition in the ministry of our Lord, for from here to the Cross, opposition would increase and He would spend most of His time preparing His disciples for their mission once He was gone.

Left  (2641)(kataleipo from kata = intensifies or strengthens the meaning of leipo + leipo = to leave behind, forsake, to be wanting or deficient) literally means to leave behind or leave remaining (of a person or place - Mt 4:13, 16:4, 21:17, Heb 11:27). Kataleipo is often used to indicate abandoning a heritage, giving up riches, and leaving one's native land. Figuratively kataleipo was used to mean "neglect" (Acts 6:2+). Kataleipo conveys a strong sense of to abandon or forsake (as forsaking true Christianity 2Pe 2:15). To cause something to be left over and so to remain in existence (Ro 11:4-note, Heb 4:1-note = a promise remains). To leave without help (Lk 10:40). In the passive to remain behind (1Th 3:1-note, John 8:9). To leave alone in the sense of disregard as describing those who sail past a place without stopping (Acts 21:3) Kataleipo can mean to cease an activity (eg, give up a vice) but there are no uses with this sense in Scripture.

Matthew 16:5  And the disciples came to the other side of the sea, but they had forgotten to bring any bread.

  • Mt 15:39 Mk 8:13,14 

And the disciples came to the other side of the sea, but they had forgotten to bring any bread - Matthew 

Matthew 16:6  And Jesus said to them, "Watch out and beware of the leaven of the Pharisees and Sadducees."

  • Take: Lu 12:15 
  • the leaven: Mt 16:12 Ex 12:15-19 Lev 2:11 Mk 8:15 Lu 12:1 1Co 5:6-8 Ga 5:9 2Ti 2:16,17 
  • the Pharisees: Mt 16:1 

And Jesus said to them, "Watch out and beware of the leaven of the Pharisees and Sadducees."

Matthew 16:7  They began to discuss this among themselves, saying, "He said that because we did not bring any bread."

  • they: Mk 8:16-18 9:10 Lu 9:46 
  • It is: Mt 15:16-18 Ac 10:14 

They began to discuss this among themselves, saying, "He said that because we did not bring any bread."

Matthew 16:8  But Jesus, aware of this, said, "You men of little faith, why do you discuss among yourselves that you have no bread?

  • when: Joh 2:24,25 16:30 Heb 4:13 Rev 2:23 
  • O ye: Mt 6:30 8:26 14:31 Mk 16:14 

But Jesus, aware of this, said, "You men of little faith, why do you discuss among yourselves that you have no bread?

Arguing over the fact that they had no bread and showing their lack of faith to remember how He had multiplied loaves and fish before. 

Matthew 16:9  "Do you not yet understand or remember the five loaves of the five thousand, and how many baskets full you picked up?

  • ye not: Mt 15:16,17 Mk 7:18 Lu 24:25-27 Rev 3:19 
  • the five loaves: Mt 14:17-21 Mk 6:38-44 Lu 9:13-17 Joh 6:9-13 

"Do you not yet understand or remember the five loaves of the five thousand, and how many baskets full you picked up?

Matthew 16:10  "Or the seven loaves of the four thousand, and how many large baskets full you picked up?

  • Mt 15:34,38 Mk 8:5-9,17-21 

Or the seven loaves of the four thousand, and how many large baskets full you picked up?

Matthew 16:11  "How is it that you do not understand that I did not speak to you concerning bread? But beware of the leaven of the Pharisees and Sadducees."

  • Mk 4:40 8:21 Lu 12:56 Joh 8:43 

How is it that you do not understand that I did not speak to you concerning bread? But beware of the leaven of the Pharisees and Sadducees."

Matthew 16:12  Then they understood that He did not say to beware of the leaven of bread, but of the teaching of the Pharisees and Sadducees.

  • but: Mt 15:4-9 23:13-28 Ac 23:8 

Then they understood that He did not say to beware of the leaven of bread, but of the teaching of the Pharisees and Sadducees

Matthew 16:13  Now when Jesus came into the district of Caesarea Philippi, He was asking His disciples, "Who do people say that the Son of Man is?"

  • came: Mt 15:21 Ac 10:38 

Strategic Location of Who Am I?

Now when Jesus came into the district of Caesarea Philippi, He was asking His disciples, "Who do people say that the Son of Man is?"

Matthew 16:14  And they said, "Some say John the Baptist; and others, Elijah; but still others, Jeremiah, or one of the prophets."

  • John: Mt 14:2 Mk 8:28 
  • Elias: Mal 4:5 Mk 6:15 Lu 9:18,19 Joh 7:12,40,41 9:17 

And they said, "Some say John the Baptist; and others, Elijah; but still others, Jeremiah, or one of the prophets

Matthew 16:15  He said to them, "But who do you say that I am?"

  • But (KJV): Mt 13:11 Mk 8:29 Lu 9:20 


He said to them, "But who do you say that I am?

This passage represents the climax of Jesus’ teaching ministry. It was, in effect, the apostles’ final examination, consisting of but one question, the ultimate question that every human being must face: Who is Jesus Christ? A person’s answer is of the most monumental importance, because on it hinges his eternal destiny It is a question that no one can escape or avoid. Every soul, as it were, will be pinned against the wall of eternity and forced to answer that question.
    For some two and a half years Jesus had been moving to this moment-teaching and reteaching, affirming and reaffirming, demonstrating and redemonstrat-ing, building and rebuilding the truth of who He was in order to establish it completely and securely in the minds and hearts of the Twelve.
    During the previous several months the Lord had largely shunned the crowds and the Jewish leaders. His few encounters with them were brief and terse. The misguided multitudes wanted to make Him their political deliverer from the military bondage of Rome and the capricious ambitions of Herod. The scribes, Pharisees, and Sadducees were, for the most part, thoroughly convinced He was a threat to their religious system and were determined to be rid of Him, if necessary by taking His life.
    As He spent more and more time alone with the Twelve, Jesus went more often into Gentile territory and stayed longer. He withdrew to the fringes of Palestine in order to be free of the misguided and fickle adulation of the multitudes and the growing hostility of the Jewish religious leaders.
The Setting

Matthew 16:16  Simon Peter answered, "You are the Christ, the Son of the living God."

  • Thou: Mt 14:33 26:63 27:54 Ps 2:7 Mk 14:61  Joh 1:49 6:69 11:27 20:31 Ac 8:37 9:20 Ro 1:4 Heb 1:2-5 1Jn 4:15 5:5,20 
  • the living: De 5:26 Ps 42:2 Da 6:26 Ac 14:15 1Th 1:9 

THOU ART THE CHRIST: Christ is the Greek equivalent of the Hebrew Messiah, God’s predicted and long-awaited deliverer of Israel, the supreme “Anointed One,” the coming High Priest, King, Prophet, and Savior. Without hesitation Peter declared Jesus to be the Messiah, whereas the multitudes of Jews believed Him to be only the Messiah’s precursor.
    On first meeting Jesus, Andrew had excitedly proclaimed Him to be the Messiah, and Nathaniel had called Him “the Son of God … the King of Israel” (Jn1:41, 49). The disciples knew that John the Baptist had borne witness that Jesus “is the Son of God” (Jn1:34), and the longer they stayed with Him, the more evidence they had of His divine nature, power, and authority.
    Like their fellow Jews, however, they had been taught to expect a conquering and reigning Messiah who would deliver God’s people from their enemies and establish forever His righteous kingdom on earth. And when Jesus refused to use His miraculous power for His own benefit or to oppose the Roman oppressors, the disciples wondered if they were right about Jesus’ identity His humility, meekness, and subservience were in total contrast to their preconceived views of the Messiah. That the Messiah would be ridiculed with impunity, not to mention persecuted and executed, was inconceivable. When Jesus spoke of His going away and coming back, Thomas doubtlessly echoed the consternation of all the disciples when he said, “Lord, we do not know where You are going, how do we know the way?” (John 14:5).

THE LIVING GOD (See XR's Ps42:2): OT name for Jehovah (Dt5:26; Jos3:10; 1Sa17:26, 36; 2Ki19:4, 16; Ps42:2;  84:2; Da6:26; Ho1:10) contrast the dead, dumb idols (Je10:8;  18:15; 1Co12:2).
    The Son of Man (v. 13) was also the Son of … God, the Creator of the universe and all that is in it. He was the true and real God, not a mythological figment such as Pan or a mortal “deity” such as caesar-both of whom had shrines in Caesarea Philippi. The disciples’ Lord was Son of the living God.
    As evidenced by numerous things the Twelve later said and did, they did not at this time have a full comprehension of the Trinity or even of the full nature and work of Christ. But they knew Jesus was truly the Christ and that He was truly divine, the Son of the living God. Son reflects the idea of oneness in essence, because a son is one in nature with his father. So Jesus Christ was one in nature with God the Father (cf. Jn5:17,18; 10:30–33).

Henry Morris - Peter's great confession apparently was given as spokesman for all the disciples since Jesus had asked them the question (Matthew 16:15). They understood that Jesus was both the promised Messiah ("the Christ") and also the only begotten Son of God. They had learned this first from John the Baptist (see John's testimony as recorded in John 1:15-18), but this had been further confirmed by their personal knowledge of Christ and by the inward witness of the Holy Spirit.

Believer's Study Bible - Peter means by his answer that Jesus is the One who would fulfill the messianic hope of the O.T. He does not completely understand the nature of Jesus' messiahship, but the truth is beginning to dawn, as Matthew makes clear by the expression "the Son of the living God." This is Peter's astonishing insight. To avow that Jesus was the Messiah was not startling. But to affirm that Jesus, the Messiah, was the Son of God -- deity in human flesh -- was an insight of momentous illumination (v. 17).

Matthew 16:17  And Jesus said to him, "Blessed are you, Simon Barjona, because flesh and blood did not reveal this to you, but My Father who is in heaven.

  • Blessed: Mt 5:3-11 13:16,17 Lu 10:23,24 22:32 1Pe 1:3-5 5:1 
  • Simon: Joh 1:42 21:15-17 
  • for: Ga 1:11,12,16 
  • but: Mt 11:25-27 Isa 54:13 Lu 10:21,22  Joh 6:45 17:6-8 1Co 2:9-12 Ga 1:16 Eph 1:17,18 2:8 3:5,18,19 Col 1:26,27 1Jn 4:15 5:20 

Blessed are you, because he had received this insight through divine revelation and not through human influences. 

God the Father removed the veil on Jesus' true identity, exposing to open view what was before hidden. He made manifest and revealed the Holy One Who was previously unknown to the apostles.

Matthew 16:18  "I also say to you that you are Peter, and upon this rock I will build My church; and the gates of Hades will not overpower it.

  • thou: Mt 10:2  Joh 1:42 Ga 2:9 
  • upon: Isa 28:16 1Co 3:10,11 Eph 2:19-22 Rev 21:14 
  • I will: Zec 6:12,13 1Co 3:9 Heb 3:3,4 
  • my: Mt 18:17 Ac 2:47 8:1 Eph 3:10 5:25-27,32 Col 1:18 1Ti 3:5,15 
  • and the: Ge 22:17 2Sa 18:4 Job 38:17 Ps 9:13 69:12 107:18 127:5 Pr 24:7 Isa 28:6 38:10 1Co 15:55 *marg:
  • shall not: Ps 125:1,2 Isa 54:17 Joh 10:27-30 Ro 8:33-39 Heb 12:28 Rev 11:15 21:1-4 

YOU ARE PETER( (Jn1:42): petros = small stone in contrast to the word that speaks more of a foundation stone, massive boulder, etc = ROCK = petra = great rock mass solid and immovable. So Jesus’ words here are best interpreted as a simple play on words in that a boulder-like truth came from the mouth of one who was called a small stone! 

AND UPON THIS ROCK (cf Ex17:6 Lxx = "petra", 1Co10:4) I WILL BUILT MY CHURCH: So is Jesus saying He will build His church upon Peter (Petros) or upon "this rock" (Petra = large boulder)? goto 1Pe2:4-8 (& before the Jewish hiearchy in Ac4:5,v6,11,12) where Peter himself explains upon Whom the church will be built. There we see Peter himself explains that Jesus is the Corner Stone, not Peter! Peter says that Jesus is the foundation. There is a sense in which the apostles played a foundational role in the building of the church (Ep2:20), but the role of primacy is reserved for Christ alone, not assigned to Peter.
    Matthew is the only gospel where "CHURCH" is found (see Mt18:17). Christ called it “My church,” emphasizing that He alone is its Architect, Builder, Owner, and Lord. The Gr. word for church = “called out ones.” While God had since the beginning of redemptive history been gathering the redeemed by grace, the unique church He promised to build began at Pentecost with the coming of the Holy Spirit, by Whom the Lord baptized believers into His body—which is the church (see Ac2:1-4; 1Co12:12,13).

AND THE GATES OF HADES SHALL NOT OVERPOWER IT: hades = that which is out of sight-- hades is down (Mt11:23), and it is a prison to which He holds the keys (Rev1:18).  “The gates of hades” symbolize of death. So Jesus is saying that DEATH could never PREVAIL or OVERPOWER believers because we are "living stones" built upon the foundation stone, the chief Corner Stone. (1Pe2:5) Hades is the place of punishment for the spirits of dead unbelievers. The point of entry for such is death. This, then, is a Jewish phrase referring to death. Even death, the ultimate weapon of Satan (cf. Heb2:14, 15), has no power to stop the church. The blood of martyrs, in fact, has sped the growth of the church in size and spiritual power. By His death and resurrection, Jesus Christ conquered death, & so gave victory over death to any who have built their future upon the Rock.     
    “Gates” represent, in the Bible, authority and power. The city gate was to a Jew what city hall is to people in the Western world. Important business was transacted at the city gate (Dt16:18; 17:8; Ru4:11). Hades is the place of punishment for the spirits of dead unbelievers. The point of entry for such is death. This, then, is a Jewish phrase referring to death. Even death, the ultimate weapon of Satan (cf. Heb2:14, 15), has no power to stop the church. The blood of martyrs, in fact, has sped the growth of the church in size and spiritual power.
    Jews would understand hades’ gates to refer to physical death. Jesus was thus telling the disciples His death would not prevent His work of building the church. Later (Mt16:21) He spoke of His imminent death. He was therefore anticipating His death and His victory over death through the Resurrection.


Recognizing God’s Institutions: Beginning @ Ge2:18
The Origin of the Church—
    The church was a mystery (that is, hidden, not revealed) in the OT. It was first prophesied in these words spoken to Peter, “on this rock I will build My church.” In this prophecy there is a play on the word “rock” which also happens to be Peter’s name. Jesus said, “you are Peter” (masculine, petros) and “on this rock [feminine, petra] I will build My church.” But when did the church actually begin? Again, many suggestions are offered for varying reasons. The simplest view is to understand the NT church as beginning on the Day of Pentecost in response to Peter’s Pentecostal sermon when “that day about three thousand souls were added to them [that is, the apostles]” (Ac2:41). This group for the first time is called “the church” in Ac2:47, and God added to their number daily those who were saved.

Now go to—Ep3:21: The Purpose of the Church.

Matthew 16:19  "I will give you the keys of the kingdom of heaven; and whatever you bind on earth shall have been bound in heaven, and whatever you loose on earth shall have been loosed in heaven."

  • give: Ac 2:14-42 10:34-43 15:7 
  • the keys: Isa 22:22 Rev 1:18 3:7 9:1 20:1-3 
  • and whatsoever: Mt 18:18 Joh 20:23 1Co 5:4,5 2Co 2:10 1Th 4:8 Rev 11:6 

Though v18 is difficult, v19 has been even more fiercely debated. However, nothing in either verse suggests the possibility that Peter was given authority to forgive men of their sins. See Wuest expanded translation below to help get the sense of this difficult passage.

I WILL GIVE YOU THE KEYS OF THE KINGDOM OF HEAVEN: These represent authority, and here Christ gives Peter (and by extension all other believers) authority to declare what was bound or loosed in heaven. This echoed the promise of Jn20:23, where Christ gave the disciples authority to forgive or retain the sins of people. All this must be understood in the context of Mt18:15-17, where Christ laid out specific instructions for dealing with sin in the church (see Mt18:15). The sum of it all means that any duly constituted body of believers, acting in accord with God’s Word, has the authority to declare if someone is forgiven or unforgiven. The church’s authority is not to determine these things, but to declare the judgment of heaven based on the principles of the Word. When they make such judgments on the basis of God’s Word, they can be sure heaven is in accord. In other words, whatever they “bind” or “loose” on earth is already “bound” or “loosed” in heaven. When the church says the unrepentant person is bound in sin, the church is saying what God says about that person. When the church acknowledges that a repentant person has been loosed from that sin, God agrees.

AND WHATEVER YOU SHALL BIND ON EARTH SHALL BE BOUND IN HEAVEN: "bind" = rabbinic term =  forbid or prohibit. Rabbis of the school of Hillel “loosed” many things that the school of Schammai “bound.” So these "keys of the Kingdom" either "prohibit" or they "permit". Prohibit or permit "what"? Entrance into the KINGDOM OF HEAVEN. The KEYS then are the MESSAGE that either UNLOCKS or SHUTS UP HEAVEN. So what you do with the truth of Jesus determines whether you will or will not gain entry into the Kingdom of Heaven. And this is exactly what Peter did in Ac2:38-40 in a sense taking the keys of the Kingdom (Mt16:19) and "opening" the "kingdom of heaven. We see the opposite in Ac4:11,12 where Peter is in essence "locking" heaven to anyone who does not believe that Jesus Christ is the only name by which a man is saved and through which he gains entrance into the Kingdom of Heaven. 
    Cp Rev1:18 where we see that Jesus has the "keys of death and of Hades". Jesus is the One who shuts up Hades or opens Hades. No one can enter in except thru His key because He holds the key. Who is given the KEYS in Mt18 
    shall be bound and shall be loosed translate future perfect passives and are more accurately rendered “will have been bound” and “will have been loosed.” Note the future perfect indicative = a state of completion.
    The Wuest expanded translation of Mt16-18,19: "And answering, Jesus said to him, Spiritually prosperous are you, Simon Barjona, because flesh and blood did not reveal this to you but my Father who is in heaven. Moreover, as for myself, I also am saying to you, You are Rock [petros, masculine in gender, a detached but large fragment of rock], and upon this massive rock [petra, feminine in gender, feminine demonstrative pronoun cannot go back to masculine petros; petra, a rocky peak, a massive rock] I will build my Church. And the councils of the unseen world shall not overpower it. I shall give to you the keys of the kingdom of heaven; and whatever you bind on earth [forbid to be done], shall have been already bound [forbidden to be done] in heaven; and whatever you loose on earth [permit to be done], shall have already been loosed in heaven [permitted to be done]."

AND WHATEVER YOU SHALL LOOSE ON EARTH SHALL BE LOOSED IN HEAVEN: "loose" = rabbinic terms = permit or allow.  (for "luo" see note under "annul" Mt5:19)
    "Keys" were the symbol of knowledge or the fruit of the scribal or teaching office (cf. Lu11:52 in which "key" refers to knowledge). 
    Peter and those with him are given the "keys of the kingdom" i.e., the gospel of Christ. The use of those keys will build the church. Peter did precisely this at Pentecost (Ac2:14), at Samaria (Ac8:14), and for Cornelius the Gentile (Ac10). The expressions "shall be bound in heaven" and "shall be loosed in heaven" are examples in Greek of the periphrastic future perfect passive construction and should, therefore, be translated "will have been bound already" and "will have been loosed already" in heaven. In other words, Peter's pronouncement of "binding" or "loosing" is dependent upon what heaven has already willed, rather than earth's giving direction to heaven.

Matthew 16:20  Then He warned the disciples that they should tell no one that He was the Christ.

  • charged: Mt 8:4 17:9 Mk 8:30 9:9 Lu 9:21,36 
  • Jesus: Joh 1:41,45 20:31 Ac 2:36 1Jn 2:22 5:1 

Henry Morris - tell no man.  The gospel records give no indication that the disciples ever acknowledged Jesus was the Christ prior to this confession of Peter's, although they almost certainly realized it. By this stage of His public ministry, He evidently planned to concentrate on teaching and training His disciples for their own future ministry.

Believer's Study Bible - Why should Jesus forestall the disciples from openly identifying Him as the Messiah? (1) Already there had been more than sufficient publicity. Additional fanfare would only increase opposition on the one hand, and give encouragement to those who still desired Him to act as a political Messiah on the other. (2) The latter days of His ministry were designed to be less public and more private for the instruction of the disciples. The time would come later for the messiahship of Jesus to be publicly proclaimed.

Ryrie - tell no one because the leaders had rejected Him and He did not want to foster revolution against Rome. 

Matthew 16:21  From that time Jesus began to show His disciples that He must go to Jerusalem, and suffer many things from the elders and chief priests and scribes, and be killed, and be raised up on the third day.

  • began: Mt 17:22,23 20:17-19,28 26:2 Mk 8:31 9:31,32 10:32-34 Lu 9:22,31,44,45 18:31-34 24:6,7,26,27,46 1Co 15:3,4 
  • chief priests: Mt 26:47 27:12 1Ch 24:1-19 Ne 12:7 
  • and be: Mt 27:63  Joh 2:19-21 Ac 2:23-32 

Henry Morris - From that time forth.  Once the disciples had formally recognized Him as the Messiah, the Lord began to prepare them for His real mission--and theirs. In spite of Jesus' teachings however, His death and resurrection caught them by surprise. Somehow they still felt He would lead them in establishing the messianic kingdom without this very uncomfortable interruption

This is Matthew's first prediction of the Passion (see also 17:22; 20:18). Notice the number of specific details in this prediction. 

Matthew Henry - Christ reveals his mind to his people gradually. From that time, when the apostles had made the full confession of Christ, that he was the Son of God, he began to show them of his sufferings. He spake this to set right the mistakes of his disciples about the outward pomp and power of his kingdom. Those that follow Christ, must not expect great or high things in this world. Peter would have Christ to dread suffering as much as he did; but we mistake, if we measure Christ's love and patience by our own. We do not read of any thing said or done by any of his disciples, at any time, that Christ resented so much as this. Whoever takes us from that which is good, and would make us fear to do too much for God, speaks Satan's language. Whatever appears to be a temptation to sin, must be resisted with abhorrence, and not be parleyed with. Those that decline suffering for Christ, savour more of the things of man than of the things of God. 

Matthew 16:22  Peter took Him aside and began to rebuke Him, saying, "God forbid it, Lord! This shall never happen to You."

NET  Matthew 16:22 So Peter took him aside and began to rebuke him: "God forbid, Lord! This must not happen to you!"

NLT  Matthew 16:22 But Peter took him aside and began to reprimand him for saying such things. "Heaven forbid, Lord," he said. "This will never happen to you!"

ESV  Matthew 16:22 And Peter took him aside and began to rebuke him, saying, "Far be it from you, Lord! This shall never happen to you."

NIV  Matthew 16:22 Peter took him aside and began to rebuke him. "Never, Lord!" he said. "This shall never happen to you!"

GNT  Matthew 16:22 καὶ προσλαβόμενος αὐτὸν ὁ Πέτρος ἤρξατο ἐπιτιμᾶν αὐτῷ λέγων, Ἵλεώς σοι, κύριε· οὐ μὴ ἔσται σοι τοῦτο.

KJV  Matthew 16:22 Then Peter took him, and began to rebuke him, saying, Be it far from thee, Lord: this shall not be unto thee.

YLT  Matthew 16:22 And having taken him aside, Peter began to rebuke him, saying, 'Be kind to thyself, sir; this shall not be to thee;'

ASV  Matthew 16:22 And Peter took him, and began to rebuke him, saying, Be it far from thee, Lord: this shall never be unto thee.

CSB  Matthew 16:22 Then Peter took Him aside and began to rebuke Him, "Oh no, Lord! This will never happen to You!"

  • began: Mt 16:16,17 26:51-53 Mk 8:32  Joh 13:6-8 
  • Be it far from thee: Gr. Pity thyself, 1Ki 22:13 Ac 21:11-13 

Henry Morris - rebuke him.  It is surprising that Peter could make such a remarkable (even Spirit-inspired) confession of Jesus as both Messiah and Son of God, then almost immediately deny Christ's word! Jesus recognized that this was really Satan speaking through Peter (Matthew 16:23)--not in the sense of satanic possession, but rather satanic persuasion. The natural man almost instinctively recoils from the idea of the atoning death and resurrection of Christ, and Satan bitterly resists it.

Matthew 16:23  But He turned and said to Peter, "Get behind Me, Satan! You are a stumbling block to Me; for you are not setting your mind on God's interests, but man's."

  • Get: Mt 4:10 Ge 3:1-6,17 Mk 8:33 Lu 4:8 2Co 11:14,15 
  • Satan: 2Sa 19:22 1Ch 21:1 Zec 3:1,2  Joh 6:70 
  • thou art: Mt 18:7 Isa 8:14 Ro 14:13,21 
  • thou savourest: Mk 8:33 Ro 8:5-8 1Co 2:14,15 Php 3:19 Col 3:2 

Believer's Study Bible - This verse attests that Jesus' death was God's affair, for Jesus rebuked Peter for not understanding God's matters. Satan's purpose would be served if Jesus' death were deterred. This interpretation is supported by 20:28 (cf. Mark 10:45), for in His death the mission of the Suffering Son of Man is realized. 16:28 No expectation of the final return of Christ is involved in these words of Jesus. Historically, three major views have been maintained by biblical scholars: (1) Jesus is speaking of His triumphal entry into Jerusalem a few days hence; (2) the reference is to the resurrection of Christ and His victory over death; or (3) because of the position this verse occupies in the text of Matthew, the reference is to the Lord's transfiguration, which follows immediately in Matthew's Gospel. Proximity of story favors the latter view, which is verified by the description given by Simon Peter in 2 Pet. 1:16 of the "coming" (parousia, Gk.) of the Lord in power.

Ryrie - Satan. Peter is sharply rebuked for aligning himself with Satan's plan to deter Jesus from fulfilling His mission. The harshness of the rebuke stems from Christ's fierce realism about the principal purpose of His coming to earth, which was to die. a stumbling block or "rock of offence" (Rom. 9:33). Perhaps a further play on the word "rock" in verse 18. 

Matthew 16:24  Then Jesus said to His disciples, "If anyone wishes to come after Me, he must deny himself, and take up his cross and follow Me.

  • If: Mt 10:38 Mk 8:34 10:21 Lu 9:23-27 14:27 Ac 14:22 Col 1:24 1Th 3:3 2Ti 3:12 Heb 11:24-26 
  • and take: Mt 27:32 Mk 15:21 Lu 23:26 Joh 19:17 1Pe 4:1,2 

MacArthur writes: This passage sets forth the heart of Christian discipleship and it strikes a death blow to the self-centered false gospels that are so popular in contemporary Christianity. It leaves no room for the gospel of getting, in which God is considered a type of utilitarian genie who jumps to provide a believer’s every whim. It closes the door to the gospel of health and wealth, which asserts that if a believer is not healthy and prosperous he has simply not exercised his divine rights or else does not have enough faith to claim his blessings. It undermines the gospel of self-esteem, self-love, and high self-image, which appeals to man’s natural narcissism and prostitutes the spirit of humble brokenness and repentance that marks the gospel of the cross.

Matthew 16:25  "For whoever wishes to save his life will lose it; but whoever loses his life for My sake will find it.

  • Mt 10:39 Es 4:14,16 Mk 8:35 Lu 17:33  Joh 12:25 Ac 20:23,24 Rev 12:11 

SHALL LOSE IT: This paradox is emphasized by the Lord Jesus often> Mt16:25; Mk8:35; Lu9:24;17:33; Jn 12:25). The same truth is also stressed by Paul (Ro12:1,v2; 2Co5:14,15; 6:9,10; Gal2:20; Phil2:5-11; 2Ti2:11,12). Dying to self and living unto God is the very essence of a truly happy and fulfilling life in this world and that to come.
    The Lord is saying that whoever lives only to save his earthly, physical life, his ease and comfort and acceptance by the world, will lose his opportunity for eternal life. But whoever is willing to give up his earthly, worldly life and to suffer and die, if necessary, for Christ’s sake, will find eternal life. Every person has a choice. He can “go for it” now and lose it forever; or he can forsake it now and gain it forever.

FOR MY SAKE: (Mk8:35 adds "& the gospel's")

Jesus presented to the disciples two approaches to life:  

  1. deny yourself            live for yourself
  2. take up your cross        ignore the cross
  3. follow Christ            follow the world
  4. lose your life for His sake    save your life for your own sake
  5. forsake the world        gain the world
  6. keep your soul        lose your soul
  7. share His reward and glory    lose His reward and glory

Matthew 16:26  "For what will it profit a man if he gains the whole world and forfeits his soul? Or what will a man give in exchange for his soul?

  • what is: Mt 5:29 Job 2:4 Mk 8:36 Lu 9:25 
  • gain: Mt 4:8,9 Job 27:8 Lu 12:20 16:25 
  • or: Ps 49:7,8 Mk 8:37 

Henry Morris - gain the whole world.  This is a remarkable profit and loss statement! The Greek word for "soul" is psuche, from which we have our English word "psychology," meaning "study of the soul." Although it can also mean "life," depending on context, the emphasis and comparison here seems clearly to refer to one's eternal soul.

Matthew 16:27  "For the Son of Man is going to come in the glory of His Father with His angels, and WILL THEN REPAY EVERY MAN ACCORDING TO HIS DEEDS.

the Son: Mt 24:30 25:31 26:64 Mk 8:38 14:62 Lu 9:26 21:27 22:69 
with: Mt 13:41,49 Da 7:10 Zec 14:5 2Th 1:7-10 Jude 1:14 
and then: Mt 10:41,42 Job 34:11 Ps 62:12 Pr 24:12 Isa 3:10,11 Jer 17:10 Jer 32:19 Eze 7:27 Ro 2:6 1Co 8:8 2Co 5:10 Eph 6:8 1Pe 1:17 Rev 2:23 22:12-15 

THEN RECOMPENSE: Cp Ps 62:12, Rev 22:12, 2Co5:9,10, 2Pe 1:11 (this verse could refer to something different bc it specifically refers to "entrance"???), Ro 2:6, Je17:10 


This scene could be in part that described by Ezekiel as yet future. At the end of the Tribulation God will regather Israel to the land of promise for the Millennium (cf. Ezek 36:14-38; 37:21-23). But first the Israelites will be required to stand before the Lord for judgment. Those who have placed their trust in Him will be allowed to enter the land and participate in His kingdom (cf. John 3:3). Those who are rebels will be judged for their sin and banished to everlasting punishment (Mt 24:31,40,41). ?? Mt 13:39,43. When does this refer to? Not sure but if it is at the end of the age it seems like it could be judgment of Jews. Mt 16:27 is also interesting.
    Although the Old Testament contains more than 1,500 prophecies of the coming of the Messiah, it was not revealed clearly to the saints of that era that His coming would be in two separate stages, thousands of years apart. The first stage would be characterized by suffering and sacrifice for sin, and the second by conquest and splendor. The central focus of the NT is on Christ’s first coming, but the 2nd Coming is mentioned directly or indirectly once in every 25v or ~ 320x!
    The OT references to a suffering Messiah and Redeemer were frequently rationalized away by Jewish interpreters or spiritualized to the point of insignificance. In the minds of most Jews in Jesus’ day, the Messiah was to come but once, as the conquering King of the earth.
Therefore as Jesus moved closer to His time of suffering & death, Jesus continued to prepare His disciples for what they all but refused to believe: that He, the divine Son of Man and the Messiah, rather than conquering His enemies and establishing His eternal kingdom on earth at that time, would first have to die at the hands of those enemies.
    Mt16:27-17:6 contains one of the great highlights of the Lord’s ministry on earth. It looks ahead to His coming that second and last time, the time of His return in exaltation and glory, when all His enemies will indeed be placed under His feet and He will establish the long-hoped-for eternal kingdom. 
    As He introduces this teaching (16:27-28), Jesus gives a promise, a warning, and then a repeat of this promise = For the Son of Man is going to come in the glory of His Father with His angels (16:27)
    Jesus referred to Himself as the Son of Man more than by any other designation, reflecting His humanness and His incarnation & His full identification with mankind as One of their own. 
    In his vision of the four beasts, Daniel looked across the entire history of mankind and saw its awesome climax [Da7:9], a scene of God, “the Ancient of Days,” sitting on His throne of judgment & after the beast (antichrist) is destroyed Daniel sees “One like a Son of Man,” [Da7:11-14].
    It was about that time of fateful judgment that Jesus was here speaking to the disciples, who desperately needed a word of encouragement. Recently they had heard much of pain but little of gain, much of suffering but little of glory, much of the cross but little of the crown. Jesus therefore assured them that He was indeed the Son of Man whom Daniel saw come in the glory of His Father with His thousands upon thousands and myriads upon myriads of holy angels to receive the kingdom and execute judgment.
    Here was Jesus’ first specific revelation to His disciples of His second coming. After just telling them that He was God in human flesh, that He was the promised Messiah, that He would build a kingdom that nothing could hinder or destroy-but that He first had to be rejected, killed, and rise from the dead-He now informed them that He will one day return in great glory and righteous judgment to establish His throne.
    In Scripture, the word glory is often used to represent the totality of God’s nature, character, and attributes. When He came to earth as a man, Jesus’ deity was veiled (cf. Php2:6-8), and there was nothing in His human appearance to mark Him as being different from other men (cf. Isa53:2). That very fact made it difficult for many Jews to acknowledge Him as the Messiah, whose divine power and glory they thought would be immediately manifest. But that was not God’s plan.
When Moses asked God, “I pray Thee, show me Thy glory!” the Lord replied, “I Myself will make all My goodness pass before you, and will proclaim the name of the Lord before you; and I will be gracious to whom I will be gracious, and will show compassion on whom I will show compassion” (Ex. 33:18-19). To witness God’s attributes is to have a glimpse of His glory, all that the fullness of His name implies.
    During the Olivet discourse, only a few days before His arrest and crucifixion, Jesus spoke again of His coming. “But immediately after the tribulation of those days the sun will be darkened,” He said, “and the moon will not give its light, and the stars will fall from the sky, and the powers of the heavens will be shaken, and then the sign of the Son of Man will appear in the sky, and then all the tribes of the earth will mourn, and they will see the Son of Man coming on the clouds of the sky with power and great glory. And He will send forth His angels with a great trumpet and they will gather together His elect from the four winds, from one end of the sky to the other” (Matt. 24:29-31). He will then come in blazing, unveiled glory, and the entire earth will be filled with that glory, just as in Isaiah’s vision (Isa. 6:3; cf. Ps. 72:19).
    The message that the Messiah would come in glory was not new. It was perhaps the messianic truth with which the Jews of that day were most familiar. Jesus now affirmed and gave a more complete perspective to that truth, a truth His disciples thought was being contradicted and frustrated both by His rejection by the Jewish leaders and by His own failure to assert His divine power and glory.

In Son of Man to Thee I Cry, an old and out-of-print hymn by an unknown author, we find these lovely truths:

He who wept above the grave,
He who stilled the raging wave,
Meek to suffer, strong to save,
He shah come in glory!

He who sorrow’s pathway trod,
He that every good bestowed-
Son of Man and Son of God-
He shall come in glory.

He who bled with scourging sore,
Thorns and scarlet meekly wore,
He who every sorrow bore-
He shall come in glory.

Monarch of the smitten cheek,
Scorn of Jew and scorn of Greek,
Priest and King, divinely meek-
He shall come in glory.

He who died to set us free,
He who lives and loves e’en me,
He who comes whom I shall see, Jesus only-only He-
He shall reign in glory!

    For those who know and love the Lord Jesus Christ, His return in glory is a comforting and thrilling promise that fills them with great hope and anticipation. Like the saints under the heavenly altar (Rev. 6:9-10), they wonder how long the Lord will allow the world to go its sinful way before intervening in sovereign power and bringing righteousness, equity, and justice to the world. They wonder with the psalmist, “How long, O God, will the adversary revile, and the enemy spurn Thy name?” (Ps. 74:10; cf. 35:17). In response to Jesus’ promise, “Yes, I am coming quickly,” they pray with John, “Amen. Come, Lord Jesus” (Rev. 22:20).
    At this point in Jesus’ ministry the disciples especially needed a word of hope from their Lord. He had just told them of His impending suffering and death and of the demanding conditions of true discipleship, of taking up one’s own cross and of giving up one’s own life in order to save it (Matt. 16:21-25). Perhaps for the first time it was becoming clear to them that the way of Christ is the way of self-denial, sacrifice, rejection, persecution, and quite possibly martyrdom. It was beginning to dawn on them that the way of Christ is the way of willing obedience at any price. It is saying no to ease, comfort, money, and pleasure and of saying yes to pain, struggle, persecution, and spiritual warfare for His sake. 

Matthew 16:28  "Truly I say to you, there are some of those who are standing here who will not taste death until they see the Son of Man coming in His kingdom."

  • There: Mk 9:1 Lu 9:27 
  • taste: Lu 2:26 Joh 8:52 Heb 2:9 
  • see: This appears to refer to the mediatorial kingdom which our Lord was about to set up, by the destruction of the Jewish nation and polity, and the diffusion of the gospel throughout the world. Mt 10:23 24:3,27-31,42 26:64 Mk 13:26 Lu 18:8 21:27,28 

Ryrie on they see the Son of Man coming in His kingdom - This was fulfilled when the disciples witnessed the Transfiguration (Mt 17:1-8), which was, in miniature, a preview of the kingdom, with the Lord appearing in a state of glory (Dan. 7:9-14). 

Henry Morris - not taste of death.  The disciples were to see Him "coming," not actually reigning, in His kingdom. This clearly referred to the remarkable vision which three of His disciples were about to see on the Mount of Transfiguration.

Morris - coming in his kingdom.  Peter confirms that they saw the "coming" of our Lord Jesus Christ, and were "eyewitnesses of his majesty...when we were with him in the holy mount" (2 Peter 1:16-18).