What does Matthew 27:35 mean?

Victims were almost always crucified naked. Jesus is almost always depicted wearing some minimal clothing in artwork. However, the balance of history and Roman practice suggests He was stripped nude as part of the shame and humiliation of crucifixion. The number of items being dispersed is given as five, in John 19:23–24. This would correspond to an entire outfit, including the undergarment. This, the tunic, seems to have been the subject of the gamble. Rather than tear the cloth, the soldiers each take an item and the last object is assigned by a game of chance.

It's believed that executioners at a crucifixion could take the victim's remaining clothing or personal effects as a bonus payment. The Roman soldiers perfectly and unknowingly fulfilled the prophecy found in Psalm 22:18: "they divide my garments among them, and for my clothing they cast lots." Luke records Jesus praying for forgiveness for these men (Luke 23:34).