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“I have spoken these things to you to avoid your being caused to stumble* Suffering and persecution causes some Christians to doubt God, and even to rebel against Him, and Jesus does not want that to happen to them. —they will excommunicate you; indeed, a time is coming when anyone who kills you will think he is offering God service! Like Saul of Tarsus—he thought he was serving God by persecuting the Christians (see Acts 23:1). And they will do these things because they have not known either the Father or me. Now I have told you these things so that when the time comes you may remember that I told you about them; I did not tell you these things from the beginning because I was with you. While Jesus was with them they enjoyed His protection.
What the Enabler will do
“Now then, I am going away to Him who sent me, yet none of you asks me, ‘Where are you going?’ But because I have said these things to you, sorrow has filled your heart. Nevertheless I am telling you the truth: it is to your advantage that I go away, because if I do not go away the Enabler will not come to you, but if I do go I will send Him to you.§ Jesus could only be physically present in one place at a time. The Holy Spirit can be in all believers all around the world all the time—clearly to our advantage.
“Now when He comes he will convict the world about sin and about righteousness and about judgment: first about sin, because they do not believe into me;* Since to believe into Jesus is the only cure for sin, to reject Him is the ultimate sin—you lock yourself into the consequences = spiritual death. 10 then about righteousness, because I am going away to my Father and you will no longer see me; The resurrection was the proof that the Father accepted the sacrifice of the Lamb (Romans 4:25, he “was raised because of our justification”)—having committed no sin of His own, Jesus could pay for ours. If He had committed sin on His own, He could not return to the Father. 11 then about judgment, because the ruler of this world has been judged. If the big boss has been judged, then no one under him will escape.
12 “I still have many things to say to you but you cannot bear it now.§ We have no record that He told them those things during the 40 days before His Ascension, so it may have been left for the Spirit to do (verse 13)—although probably a lot happened during those days that is not recorded. 13 However, when He, the Spirit of the Truth, has come, He will guide you into all the truth; for He will not speak on His own, but He will speak whatever He hears.* Whenever the Son spoke, it was really the Father speaking (John 12:50); the same is true of the Holy Spirit. The Trinity works together. He will also communicate to you the things that are coming. 14 He will glorify me because He will take of what is mine and communicate it to you. 15 All that the Father has is mine; Wow! that is why I said that He takes from what is mine and will communicate it to you.
Sorrow to joy
16 “In just a little you will not see me, and in another little you will see me, because I am going to the Father.” Perhaps 0.5% of the Greek manuscripts, of objectively inferior quality, omit “because I am going to the Father” (as in NIV, NASB, LB, TEV, etc.). 17 Then some of His disciples said among themselves: “What is this that He is telling us, ‘In just a little you will not see me, and in another little you will see me,’ and because ‘I am going to the Father’?” 18 So they said: “What is this ‘little’ that He mentions? We do not know what He is talking about.”§ With hindsight it appears that the first ‘little’ referred to the less than 24 hours before His burial, when He would be hidden from view. The second ‘little’ would refer to the forty days between resurrection and ascension, during which they did indeed see Him.
19 Well Jesus knew that they were wanting to question Him and said to them: “Are you inquiring among yourselves about what I said, ‘In just a little you will not see me, and in another little you will see me’? 20 Most assuredly I say to you that you will weep and lament, but the world will rejoice; you will become grieved,* This refers to the first ‘little’—upon His death they will really be grieved. but your grief will be turned into joy. This refers to the second ‘little’—upon His resurrection there will be joy. 21 When a woman gives birth she has pain, because her time has come; but when the child is born she no longer remembers the anguish, for joy that a human being has been born into the world. 22 So in your turn you are now experiencing grief, but I will see you again and your heart will rejoice, and no one will take your joy from you. 23 In that day Perhaps the ‘day’ here is different from the one in 14:20; and yet, even after seeing the risen Lord, they still got discouraged. By the sea shore Peter still asked Him a question, so maybe the ‘day’ is the same as in 14:20. It was the coming of the Holy Spirit that gave them joy that could not be stolen. you will not question me about anything.
“Most assuredly I say to you that whatever you ask the Father in my name He will give you. 24 Until now you have not asked anything in my name. Ask and you will receive, so that your joy may be made full.
Figures of speech
25 “I have told you these things using figures of speech, but a time is coming when I will no longer talk to you with figures of speech; rather I will tell you plainly about the Father. 26 In that day you will ask in my name; I do not say to you that I will request the Father on your behalf, 27 because the Father Himself is fond of you,§ The verb is φιλεω, not αγαπαω. in that you have become fond of me and have believed that I came forth from God. 28 I did come forth from the Father and have come into the world. I am leaving the world again* Jehovah the Son had visited this world many times during the OT period. During the 33+ years of incarnation He changed His abode (John 1:14). and am going to the Father.”
29 His disciples say to Him: “Hey, now you are speaking plainly and using no figure of speech! 30  Now we know that you know everything and don't need anyone to question you. They seem to be implying that before He was confused and needed help; their questions made Him think things through, or some such thing. But now He finally got it sorted out! (If it were not so pitiful it would be humorous.) By this we believe that you came forth from God.” I frankly don't understand the disciples' reasoning here. How about all His miracles, etc. etc.?
“Take heart!”
31 Jesus answered them: “Do you believe now, really? 32 Listen, an hour is coming, actually it has already arrived, that you will be scattered, each to his own, and you will leave me alone.§ It happened that very night. Yet I am not alone, because the Father is with me. 33 I have spoken these things to you so that in me you may have peace. In the world you have oppression;* Just so. Any system dominated by Satan will be oppressive, for everybody, but his special malice will be directed at those who serve Christ. but take heart, I have conquered the world!” Yes, amen! I take it that the ‘world’ here refers to the world system controlled by Satan. Jesus did indeed conquer it. He lived within that system for 33 years without ever succumbing to it, without ever being tainted by it. Since He conquered the world, we can too! So let's take heart!

*16:1 Suffering and persecution causes some Christians to doubt God, and even to rebel against Him, and Jesus does not want that to happen to them.

16:2 Like Saul of Tarsus—he thought he was serving God by persecuting the Christians (see Acts 23:1).

16:4 While Jesus was with them they enjoyed His protection.

§16:7 Jesus could only be physically present in one place at a time. The Holy Spirit can be in all believers all around the world all the time—clearly to our advantage.

*16:9 Since to believe into Jesus is the only cure for sin, to reject Him is the ultimate sin—you lock yourself into the consequences = spiritual death.

16:10 The resurrection was the proof that the Father accepted the sacrifice of the Lamb (Romans 4:25, he “was raised because of our justification”)—having committed no sin of His own, Jesus could pay for ours. If He had committed sin on His own, He could not return to the Father.

16:11 If the big boss has been judged, then no one under him will escape.

§16:12 We have no record that He told them those things during the 40 days before His Ascension, so it may have been left for the Spirit to do (verse 13)—although probably a lot happened during those days that is not recorded.

*16:13 Whenever the Son spoke, it was really the Father speaking (John 12:50); the same is true of the Holy Spirit. The Trinity works together.

16:15 Wow!

16:16 Perhaps 0.5% of the Greek manuscripts, of objectively inferior quality, omit “because I am going to the Father” (as in NIV, NASB, LB, TEV, etc.).

§16:18 With hindsight it appears that the first ‘little’ referred to the less than 24 hours before His burial, when He would be hidden from view. The second ‘little’ would refer to the forty days between resurrection and ascension, during which they did indeed see Him.

*16:20 This refers to the first ‘little’—upon His death they will really be grieved.

16:20 This refers to the second ‘little’—upon His resurrection there will be joy.

16:23 Perhaps the ‘day’ here is different from the one in 14:20; and yet, even after seeing the risen Lord, they still got discouraged. By the sea shore Peter still asked Him a question, so maybe the ‘day’ is the same as in 14:20. It was the coming of the Holy Spirit that gave them joy that could not be stolen.

§16:27 The verb is φιλεω, not αγαπαω.

*16:28 Jehovah the Son had visited this world many times during the OT period. During the 33+ years of incarnation He changed His abode (John 1:14).

16:30 They seem to be implying that before He was confused and needed help; their questions made Him think things through, or some such thing. But now He finally got it sorted out! (If it were not so pitiful it would be humorous.)

16:30 I frankly don't understand the disciples' reasoning here. How about all His miracles, etc. etc.?

§16:32 It happened that very night.

*16:33 Just so. Any system dominated by Satan will be oppressive, for everybody, but his special malice will be directed at those who serve Christ.

16:33 Yes, amen! I take it that the ‘world’ here refers to the world system controlled by Satan. Jesus did indeed conquer it. He lived within that system for 33 years without ever succumbing to it, without ever being tainted by it. Since He conquered the world, we can too! So let's take heart!