When the rich man claims to have kept all the commandments, Jesus shocks everyone by telling the young man he needs to sell all his possessions and give them to the poor (19:21-22).
If the rich man wants to be perfect, he must sell everything. He is to sell all his possessions, not just some of them. Jesus does not tell him to sell one valuable piece of property and give that money away.
Jesus and his disciples live a life of voluntary poverty. The twelve have left everything to follow Jesus. If you really want to be part of the kingdom of heaven, you need to radically follow Jesus! This demand may anticipate the call for early Christ-followers in Jerusalem to sell property to support the community. The demand is like the Community Rule at Qumran. If one was to live with the community at Qumran, they had to sell possessions and deposit that money with the leaders to support community. Davies and Allison also cite the “self-imposed poverty of Hanina ben Dosa (b. Ta’an. 24b–5a)” (Matthew, 3:46).
Did Jesus really want the man to give away all his possessions? Is this a test? In any case, the man “went away in sorrow” since he was very wealthy. Since the question was more or less “how much should I give in order to guarantee entry into the Kingdom?” Jesus responds by demanding everything!
In Second Temple Judaism, alms are called “deeds of living kindness” and considered equivalent to serving in the Temple:
m.Pirqe Abot 1:2 Simeon the Righteous was one of the last survivors of the great assembly. He would say: “On three things does the world stand: On the Torah, and on the Temple service, and on deeds of loving kindness.”
In any case, the man walks away upset. The word λυπέω can refer to physical pain, but also annoyance, irritation, or offense. In the previous parable, the other servants were upset the unmerciful servant was thrashing another servant who owed him some money, there the word may have had the nuance of offended or even grieved. In the next unit, Jesus tells a parable about workers in a field who are all paid the same wage regardless of how long they worked (20:1-16).
Jesus does not demand other rich followers sell everything. In Luke 19:1-8 Zacchaeus gave away some of his wealth. Lazarus appears to be a wealthy follower of Jesus, but there is no evidence Jesus told him to sell everything (John 12:1-3).
Is this demand to sell everything an anticipation of the early Jerusalem church? In Acts 4:32-5:11, the early Jerusalem community sells property while they wait for Jesus to return to establish the kingdom. In fact, it is quite dangerous to sell property and keep some back for yourself! It is true Jesus’s followers continued to live a life of voluntary poverty, but the money they shared supported the community. Jesus tells the rich man to give his money to be given to the poor, not to Jesus’s community fund. The demand to give the cash to a poor person rather than to the church to distribute is radical!
Imagine a church that told its congregation to help the poor directly. Go into poor neighborhoods and give food and clothing directly to the poor! In a modern church context, there might be some resistance (Because we want a tax receipt? I want my name on the donor’s list? A nice plaque on the wall?) There are good reasons in a modern context to give money to non-profit organizations who distribute food and other needs to a particular community.
The radical idea in Jesus’s demand here is that the rich give it all away without any concern for the benefit they might receive for their donations.