Verse 2: As a border city, Jericho had a customs station. As one of Palestine’s wealthiest cities, in Judea’s most fertile region, Jericho would provide particularly lucrative tax business. It had a massive sunken garden, a Herodian palace (especially for winter use, given the inviting climate) and other wealthy domiciles. As a “chief” tax gatherer, Zaccheus would hire lower tax collectors and would contract for sales and customs taxes. But while Zaccheus could thus have acquired wealth without cheating, he apparently cheated anyway (19:8).
3: Many men in this era were about five feet tall, so Zaccheus would be shorter than this. People often paid more attention to tall people (though Zaccheus by virtue of his office commanded attention).
4: Unlike the Judean hill country, Jericho had a pleasant climate throughout the year. It was known especially for its palm trees (hence one of its traditional titles, Deut 34:3; 2 Chron 28:15) but also had many other trees, including sycamores. The kind of “sycamore” mentioned here resembles a fig tree and was easy to climb; it differs from the North American sycamore and European and Asian sycamore maple.Although houses in OT Jericho were closely packed, NT Jericho hosted spacious villas and parks, so a tree was handier than a rooftop.
5: Regardless of one’s status, one did not normally invite oneself to another’s home. Also unusual is Jesus’ willingness to accept table fellowship, which normally created a bond of friendship. Pharisees would not trust the table of a tax gatherer, because anyone unreligious enough to collect taxes certainly could not be trusted to tithe foodstuffs.
Jewish people recognized that one who could call the name of a person they had not met was a prophet. Because the journey to Jerusalem from Jericho was about 17 miles uphill (nearly a day’s journey), Jesus may have preferred to let his disciples rest in a place with sufficient accommodations before continuing their journey.
8: Zaccheus’ promise to make restitution treats his exploitation as theft (Ex 22:1-4). Pharisees, who tended to be lenient on legal punishments, required four- or fivefold restitution only for stolen oxen or sheep that were slaughtered or sold, and only if this was verified by witnesses. Zaccheus goes beyond this. Moreover, Judaism traditionally thought of restitution to receive forgiveness, but here it responds to grace instead of invites it.
Zaccheus could not imprison someone on his own authority, but he could make false reports to produce that outcome; his office would thus have given him power to intimidate and secure his demands, if he wished to do so.
9: Jewish people believed that God had made a covenant with Abraham’s descendants, so that most were destined for life except those who broke God’s covenant.
10: In Ezek 34:6, 11, when the leaders of God’s people failed to care for the sheep, God himself sought out the lost sheep.
(Adapted from Dr. Keener’s personal research. Used with permission from InterVarsity Press, which published similar research by Dr. Keener in The IVP Bible Background Commentary: New Testament. Buy the book here.)