What does Luke 23:32 mean?

As Jesus walks to Golgotha to be crucified, two other men carry their crossbeams on the same march. They are lawbreakers—"malefactors" in the King James Version—who have committed serious crimes. Matthew 27:38 and Mark 15:27 say "robbers," which refers to something like a bandit or a plunderer. Luke uses a word also found in 2 Timothy 2:9, where Paul says he is bound as a criminal. Considering the sentence of crucifixion for these two men, it seems they were rebelling against Rome in some way.

Jesus being crucified with these men is a fulfilment of prophecy. The night before He told His disciples, "And let the one who has no sword sell his cloak and buy one. For I tell you that this Scripture must be fulfilled in me: 'And he was numbered with the transgressors.' For what is written about me has its fulfillment" (Luke 22:36–37). The prophecy is about the Suffering Servant:

"Therefore I will divide him a portion with the many,
and he shall divide the spoil with the strong,
because he poured out his soul to death
and was numbered with the transgressors;
yet he bore the sin of many,
and makes intercession for the transgressors" (Isaiah 53:12).

That single verse is a treasure trove of prophecy. As it relates to Luke's account, the last line is most poignant. Jesus does make intercession. One thief declares that Jesus is innocent, his words contradicting the crowd that denies Jesus is Christ. Then he asks Jesus, "Jesus, remember me when you come into your kingdom." Jesus says, "Truly, I say to you, today you will be with me in paradise" (Luke 23:39–43). As Jesus holds the wrath of God, He assures the thief of his reconciliation with God.

Many extra-biblical writings claim details about the lives of these two thieves. The Bible, itself, says little about them.