High Priest would see Jesus in clouds
Mat 26:63 But Jesus was silent. And the high priest answered and said to Him, “I adjure you by the living God that you tell us if you are the Christ (Messiah), the Son of God.”
Mat 26:64 Jesus said to him, “You have said, moreover I say to you, soon you shall gaze at the Son of Man sitting on the right side of power, and coming upon the clouds of the sky.”
Mat 26:65 Then the high priest tore his clothes, saying, “He has blasphemed! What further requirement have we of witnesses? Behold, now you have heard his blasphemy.
Mat 26:66 What do you think?” They answered and said, “He is guilty of death.”
One of the two High Priests at that time was High Priest Caiaphas (Luke 3:2.) The other was High Priest Annas. Annas' daughter had married Caiaphas so Caiaphas was son-in-law of Annas. The chief priests, scribes and elders of the Judaists (Jews) met at Caiaphas' palace (Math 26:3) and plotted to kill Jesus (Math 26:4) so we know that the trial was never going to be a fair one.
High Priest Caiaphas told the Pharisean Council that it was better for Jesus to die than for the whole of Judaism be destroyed by the Romans (John 11:50) and from that day the Council began plotting to kill Jesus (John 11:53). There we note that Caiaphas' statement was a prophecy of Jesus' death but more importantly indicating that Jesus' death would serve 2 purposes - die for Judeans but also gather together the children of God from all the places where they had been scattered. Thus Jesus would reunify the House of Judah (resident tribes in the land of Israel) and the House of Israel (scattered tribes in the lands around Israel) which had been split since the Assyrian conquest hundreds of hears before.
On the day of the arrest, the soldiers first took Jesus to the High Priest Annas (who was the father-in-law of the High Priest Caiaphas.) Annas (John 18:19) asked Jesus about his disciples and about his teachings. Jesus replied that he always taught openly to Judeans (Jews) wherever they were gathered, such as in the synagogue and temple. Jesus said he had nothing to hide and suggested that Annas ask his audience what he had said. At which point a soldier slapped Jesus for answering Annas like this. Annas had Jesus bound and sent to High Priest Caiaphas (John 18:24.)
The high priests and elders and the whole Jewish Sanhedrin Council were assembled with the High Priest Caiaphas. So the trial was not a public one but a private one among the leaders of Judaism. The only exceptions were two false witnesses who had been called to testify (verse 60.)
From High Priest Caiaphas, Jesus was taken by the chief priests and officers of Judaism (John 19:6) to the Praetorium, to the Roman Governor Pilate's Hall of Judgement (John 18:28) for Pilate to question Jesus. Only the Romans could put someone to death. Pilate wanted to release Jesus but asked the chief priests and officers what should be done and they gave reasons why Jesus should die. Ultimately, Pilate relented and arranged his crucifixion.
Later High Priests Annas and Caiaphas put Peter and John on trial in Jerusalem (Acts 4:6.) But lacking a reason to hold them, let them go forbidding them to speak about Jesus (verse 21.)
Text Comments - Math 26:63-66.
Jesus was silent in the face of the two human false witnesses but when the High Priest charged Jesus on oath before the living God (Yahweh Elohim) to answer if he was the Messiah, Jesus replied. Rather than agreeing he was the Messiah, he stated that the High Priest had stated it so. And since the High Priest had stated it, then it was true.
Jesus didn't let the matter end there. Before he was judged guilty, Jesus needed the High Priest to know that the High Priest was gravely mistaken in his analysis and judgement on Jesus.
Jesus told the High Priest that he himself would see Jesus (the Son of Man) sitting on the right of power (ie of Yahweh Elohim) and coming on the clouds of the sky. This meant that the High Priest would still be alive when Jesus returned on the clouds, proving yet again that Jesus' return happened within their generation and before all the apostles had died. Jesus confirmed this in John's revelation in Rev 1:7 stating “He comes with the clouds and every eye will see Him and those who pierced Him will see Him.” So not only would the High Priest see Jesus come on the clouds but also those others who had arranged for His crucifixion, as well as all the eyes of Judea for it was over Jerusalem that Jesus was to come.
The High Priest tore his clothes, indicating a serious breaking of the teaching of Judaism and confirmed this by stating that Jesus had spoken blasphemy. The blasphemy was stating that as the Messiah, Jesus sat alongside Yahweh Elohim and would be above the High Priest (literally and figuratively.)
The High Priest let the people at the trial decide (ie the Sanhedrin Council) and they chose death for Jesus on the stated grounds.
When Jesus came back around 70AD at the judgement and fall of Jerusalem, the High Priest Caiaphas would have seen Jesus come on the clouds. Caiaphas would have been duly amazed and wretched to realise that he had judged the Messiah Himself and missed knowing personally the very One they had been waiting for so long a time.