This passage occurs in the Narrative Lectionary Year 4 Lenten Cycle, most recently, March 30, 2015.
Summary: Pilate's character in the Gospel of John is complex. It seems that John wants to drive home the point that not even Pilate is in control of the situation, but only Jesus. Pilate's interview haunts us with the question: What is truth? The answer is obviously Jesus, but what does that mean? And yes, our answer should be slightly offensive. It got Jesus killed; it should at least get us in a little trouble.
μαρτυρεω ("testify", literally martyr, vs 18:37) This word means to give a witness, like in court. Jesus takes his place as the first Christian martyr, one who will be killed for the truth. So many Christians died giving their witness that the word's meaning changed.
βασιλευς ("king", vs. 18:33,37) BDAG define this as "One who rules as possessor of the highest office in a political realm." Already this shows Pilate considers the whole trial as a sham. Could Pilate really execute the king of the Jews? Obviously not.
κοσμος ("world", literally cosmos, vs 18:37) Just a reminder: God loves the world, but the world doesn't love back:
Throughout the Gospel of John, the world doesn't like God. It doesn't
understand God (1:10); it doesn't give like God (14:27) ; in fact, it hates God
(7:7). Yet God loves it still.
αληθεια ("truth", vs 18:37,38) BDAG writes, "truth is a favorite word of the Johannine literature" and play a major role in it.
John 17:17 God's word is truth
John 14:6 Jesus is the truth
John 16:13 Spirit leads to truth
John 8:32 Truth sets on free
Βαραββας ("Barabbas", vs. 40) This word literally means "Son of the Father." Quite an irony that "Son of the father" is chosen and its not Jesus! This also picks up on the irony that the Jewish leaders are concerned about ritual purity as they hand Jesus over to death (18:28)
ληστης ("thief", vs. 40) The word means robber. But Josephus, a Jewish historian writing during this time, always uses this word to mean social bandit/revolutionary, it clearly can mean this too. If you totally cannot focus on your sermon, you can read about what Josephus says about Jesus here: