We might interpret Luke’s words: who Jesus was (Luke 19:3) to mean Zacchaeus simply couldn’t pick Jesus out from the crowd, because of all the people in from of him. Zacchaeus was a small man, and his visibility was negligible due to all the people who lined the roadway that Jesus used from Jericho to Jerusalem.
Folks tend to see what they want to see. Some will even deny what they know to be true, in order to maintain what they want to see. Certainly, many folks would have considered Zacchaeus to be an evil, wicked person for joining with the Romans to tax the people, but the people would have been taxed whether or not Zacchaeus acted as a Roman agent. What would Jesus think of him? How would Jesus see Zacchaeus? Perhaps these were questions Zacchaeus thought about when he found out Jesus was passing by.
Had Zacchaeus met Jesus’ before? It is difficult to understand how he might recognize Jesus over the heads of the crowd, if he hadn’t met him before this time (cf. Matthew 26:48). It is almost certain that Zacchaeus, being a chief tax collector, would have heard about Jesus’ relationship with other publicans or tax collectors (Luke 15:1). It is possible that Zacchaeus had already met Jesus. He may have been one of the guests at the great feast Matthew (Levi) made in Jesus’ honor (Luke 5:29). Perhaps Zacchaeus wanted to see for himself, if Jesus would accept even him, whom the people hated so much. It is also possible that Zacchaeus wanted not only to see Jesus, but deeply desired for Jesus to see him. He may have thought it inappropriate to actually ask Jesus to be a guest in his home (cf. Luke 7:6-7), but given Jesus’ reputation of receiving tax collectors (Luke 15:1), he may have secretly hoped Jesus would initiate the idea, himself (Luke 19:5).
If Zacchaeus couldn’t see Jesus, how might this fit into Matthew’s account of two blind people healed just outside of Jericho (cf. Matthew 20:29-30)? This is an interesting idea, and, comparing the two accounts, it is possible for Matthew’s second blind man to be Luke’s Zacchaeus wanting to see Jesus but unable to do so. Moreover, if the above is true about Zacchaeus’ desire to know if Jesus would accept him, that desire to see Jesus could only be healed by Jesus, himself. Of course, we cannot say that this understanding is accurate, but it is also an interesting point that cannot be expelled with certainty.
In order to see Jesus, Zacchaeus ran ahead of the crowd that lined the street and climbed a sycamore tree (Luke 19:4). The sycamore tree, which Zacchaeus climbed was nothing like the American sycamore. This tree had a short trunk with large limbs running out in every direction. It was a sycamore-fig tree and very easy to climb (cf. 1Kings 10:27; Isaiah 9:10; Amos 7:14). I see in Zacchaeus a similar heart to that of the father in the Parable of the Prodigal Son who ‘ran’ to meet his son (Luke 15:20). Neither did Zacchaeus care how his unorthodox behavior (running, climbing a tree) looked to others. Not only might he have wanted to make sure he wouldn’t miss Jesus, but, possibly, he also wanted to be certain Jesus wouldn’t miss seeing him in such a place as a tree.
It probably would have been difficult for Jesus not to see Zacchaeus standing or sitting in a tree on the roadside just outside Jericho. Neither would it have been difficult for Jesus to imagine why Zacchaeus was there. He wanted to see how Jesus would react, so Jesus reacted as he had always done for folks seeking his acceptance. By saying he wished to dine with Zacchaeus and lodge overnight in his home meant that Jesus didn’t consider Zacchaeus unclean, as the Pharisees and Sadducees had taught.