What does John 11:50 mean?

Once again, Caiaphas insults the understanding of his audience. That audience happens to be composed of fellow leaders and scholars (John 11:47–49). It's statements such as this which give Caiaphas his extraordinarily poor reputation in popular fiction and drama. He's often imagined as the stereotypical Pharisee—ironic, since he was a Sadducee, and didn't hold to rigid Pharisaical interpretations of the Jewish Scriptures. He was appointed to his position by the Romans, though it's possible that the Jewish people informally considered others, such as Annas (Acts 4:6; John 18:13), to be their "real" spiritual leader.

The Scribes and Pharisees are concerned that Jesus' teachings are heresy. They are worried that Jesus will lead the people away from what they feel is the best approach to God's laws and His Word. Of course, they are also—probably more so—concerned about the threat of Jesus undermining their authority and reputations (John 11:48). That stubbornness persists even in the face of Jesus' great miracles, most recently the resurrection of Lazarus (John 11:43–44).

The Sadducees, including Caiaphas, are far more worried about Jesus' political impact. In then-recent history, Jewish unrest was met with the full might of Roman military strength. In a sense, these men are correct to worry that Rome's anger might result in the total annihilation of their culture. They ignore the fact that Jesus is not taking on political power (Acts 6:15; John 6:25–27), and will play up His risk as a rebel to Rome in order to have Him killed (John 11:53). His later triumphal entry (John 12:12–19) proves their fears partly correct: had Jesus wanted it, the people were ready to follow Him.

Caiaphas' worries and statement are both prophetic. Jesus' death is, in fact, meant as an alternative to the death of sinners (2 Corinthians 5:21; 1 Peter 3:18). His single sacrifice prevents countless souls from being separated from God for eternity (John 11:52).

Sadly, concerns about Rome crushing Israel will also to come to pass. The sacking of Jerusalem in AD 70, including the destruction of the temple (Hebrews 8:13), will come as a result of Jewish leaders pushing their people to antagonize Rome.