This parable is difficult to understand and even more difficult to preach. In no way do I presume to have the answer for you. I will, however, offer some exploratory thoughts on one way I might approach it for preaching.

What I like about this parable is the soliloquy in the center. Notice how, in the parable, the narrative pauses for a moment. We move from action to reflection. The manager finds out he is going to be fired and, before he engages in action, he debates with himself what he should do (v. 3-4).

While most people will be unfamiliar with the business practices of first-century Palestine, I do believe they will be able to identify with this moment. In times of personal crisis, people retreat from action into contemplation. They need to figure out what to do.

What is even more interesting to me is how this soliloquy is familiar. It mirrors the parable Jesus has just told. The younger son, standing out in the field with the pigs, is another figure in crisis mode. Before he takes any action, he debates with himself what he should do (15:17-19).

When Jesus told this parable, he was continuing a conversation. Those who were listening had heard the younger son’s anguish and deliberations. Now they were hearing something similar happen again. So, Jesus offers two moments of personal anguish and self-reflection; the first to the Pharisees (15:1-3) and the second to the disciples (16:1) with the Pharisees listening in (16:14). I believe you could build a sermon around these two soliloquies and the way they fit into their respective parables.

To use contemporary language, I would call these moments “come to Jesus” moments. It is the crisis in life which lays everything bare and causes you to confess. You are honest about yourself, honest about your situation, and try to find some way to make it through. This last aspect of the “come to Jesus” moment is crucial. How do these characters try to make it through?

For both of them, it is a gamble. A gamble on grace.

The younger son, like the manager, has squandered riches (see the parallel between 15:13 and 16:1). In his case, his squandering brought about his poverty and, during a famine, no one offered to take him in. Left out in the field with the pigs, he tries to figure out what he can do and he gambles on the graciousness of his father. He will come to him, confess his sin, and asked to be treated like a hired servant, no longer a son. He gambles on the graciousness of his father.

In the case of the manager, his squandering has led to his being fired. He has not come to the realization of his error on his own (like the younger son). Instead, it has been thrust upon him. His squandering has come to the ears of the rich man and he is out. He, too, however, gambles on grace. He reduces the debts the clients owe the rich man trusting that the clients, for such grace, will offer him support when he is out of work.

In both cases, these men gamble on grace and, in both cases, these men are taken off-guard. The grace they encounter is greater than the grace they imagined.

The father does not even listen to the younger son’s confession. He takes him back, not as a servant but as a son and throws him a feast. The manager finds the welcome he sought, but not from the people he expected. We are never told what the clients say of the manager, but we are told the rich man was impressed by the manager’s shrewdness and commends him for it.

What does this have to say to us, today?

First, it encourages us in daily repentance. When you think about it, “come to Jesus” moments are not that frequent in life. A divorce, a death, bottoming out because of alcohol or drug abuse, these could be “come to Jesus” moments. But they are not something that happens everyday. And because they do not happen everyday, many people just go with the flow and become accustomed to their sin.

Some, like the younger son, wait till their sin catches up with them. Others, like the manager, wait until they are found out. Many just hope it will never happen. But Christians are different. We live in daily repentance rather than apart from it. We “come to Jesus” every day, recognizing our lives would be lost if left to ourselves.

Second, it reveals that to gamble on grace is actually not the answer. Both of these men have schemes and both of them are useless. For the younger son, he does not even get to finish his sentence. His father is already running out to welcome him home. For the manager, his scheme succeeds but not in the way he imagined. He does not receive other people’s mercy, instead he receives commendation from the rich man.

Third, because these schemes are ultimately useless, the parables suggest grace is already there. Abundant. Overflowing. In Jesus.

Think about it. If anyone could be accused of squandering riches, it would be Jesus. The Pharisees have seen Him squander the blessings of God on tax collectors and sinners. He did it then. He does it now, for you and me. Even when He was crucified, He was praying for those who crucified Him.

I think of the powerful scene in Luke when Jesus is crucified. The soldiers are gambling for His cloak, while Jesus is crying out for their pardon (23:34). Gambling on grace is not the answer. God’s gracious cloak comes to us, without our gambling. It comes as a gift. Instead of a “come to Jesus” moment, we are blessed today and every day by Jesus coming to us with grace beyond our imagination.

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Additional Resources:

Concordia Theology-Various helps from Concordia Seminary in St. Louis, MO to assist you in preaching

Luke 16:1-15.

Text Week-A treasury of resources from various traditions to help you preach Luke 16:1-15.

Lectionary Podcast-Dr. David Scaer of Concordia Theological Seminary in Ft. Wayne, IN walks us through Luke 16:1-15.