The Parables of Jesus | “Lessons From a Con Man” | Luke 16:1-9

By the Rev. Justin Clemente. Preached September 19 at New Creation Church (Anglican). Part of our ongoing series on the Parables of Jesus.

Today, we continue in our series on The Parables of Jesus. We’re looking now at our third parable of Wisdom and Folly: The Parable of the Shrewd Manager. This parable can be found on page 875 of your Pew Bible.


 O Lord, may all who hear this Gospel today receive it, and know themselves to be within it. Through Christ our Lord. Amen.

Nature provides with us ample examples of basic wisdom that humans sometimes lack, spiritually speaking. We see the Ruby-throated Hummingbird who knows how to prepare for and make, in less than a single day, the 500 mile journey across the Gulf of Mexico. We see the squirrel in our yard who, constantly digging, knows how to save up for the long winter ahead. Even fish know what depth of water to stay in during the colder months. But people are often ill-prepared for and foggy-minded when it comes to God’s kingdom.

And in this need, is where our parable meets us this morning. We’re talking about lessons from a con man this morning. That seems like an unlikely topic for a Sunday morning, doesn’t it? But let’s understand this: it is not for his dishonesty and underhandedness that Jesus commends this man, but rather for his shrewdness and cleverness (and this is not the only time Jesus uses a bad example to make a good point – c.f. Luke 18:1-8).

J.C. Ryle wrote, “The diligence of worldly men about the things of time, should put to shame… coldness…about the things of eternity.” (Expository Thoughts on the Gospels) That, in a nutshell, is the point of our story today. The parable involves money, but it is not just about money. It’s about the core of Christianity – God, grace, sin and salvation.

So today, using James Boice’s insightful breakdown (The Parables of Jesus, ch. 12), we’re going to look today at three lessons from the Prudent Steward.

I. He is Commended for His Clear Thinking (vs. 3-7)

“I have decided what to do!” (v. 4)

Having been caught in the misuse of his master’s possessions, he is clear-headed about his situation.

First, when he is brought before the master, what does he do? Does he shift blame? Does he deny the allegations? No. Listen to Ken Bailey here:

“The steward’s silent acceptance of dismissal is stunning. For decades I have both observed and questioned Middle Easterners in positions of authority and have never seen or heard of a case of underling, when dismissed, walking out of the room without pleading to be reinstated. Such behavior is unimaginable. Its theological significance must not be overlooked. From Adam onward, sinners, when confronted by God, never successfully offer excuses for the evil they have done, but like Adam they often try.” (Ken Bailey, Jesus Through Middle Eastern Eyes, pg. 336) This man owned his predicament.

Secondly, what is his whole reasoning and response to the pickle he’s in based on? The merciful character of the Lord of the estate. He stakes his whole plan on the nature of the Master. Let elaborate on that to make sure I get the point across.

When steward knows he going to be fired, he quickly gathers the debtors and begins to write off their debt (and these are massive, life-changing amounts), but the debtors think the Master is the one telling the steward to do this. So this puts the Master in bind. Will he take back the write-offs? Will he take it out on the steward? Or will he stand by what’s been done by steward, and therefore be celebrated by the community as the most merciful Lord there ever was? This is why Jesus commends the dishonest manager. Ken Bailey is again helpful:

“Each debtor makes the suggested changes in his rental agreement and returns to the village to share the…good news with family and friends. As word spreads in the village a festive mood breaks in celebration of the most generous man who ever rented land in the history of the village and in praise of his steward who convinced the master to make huge reductions in their rents.” (Jesus Through Middle Eastern Eyes, pg. 340)

It’s easy to forget that this parable comes on the tail of the Parable of the Prodigal Son. Now that parable is just as much about the merciful father as it is the predicament of the younger son. And there, after having squandered the father’s wealth, it is the character of the father that shines forth when he returns home. It is all about the Prodigal God.

Each Christian is a rebellious scoundrel brought home with no excuse for his actions. And, as such, each Christian brought home proves the character of God. Do you know both of those well this morning? Maybe there is someone here today or watching online who thinks, if I were to come home to God, what would he do with me? Well, here is your answer.

II. He is Commended for His Care for the Future (vs. 4, 9)

“…so that when I am removed from management, people may receive me into their houses.” (v.4)

The con man cared for his future and followed through on it. He made sure that he would be provided for. He insured himself against what was surely coming. The spiritual parallels are obvious. James Boice here asks:

“Have you ever talked to an insurance agent? If you have not, your first conversation can be overwhelming in the sense that you would never have believed the kinds of things you can be (and according to the agent, should be) insured for. Most of us know about life insurance – but there are several kinds of that. There is also disability insurance, health insurance, dental insurance, car insurance (in several categories), home owners’ insurance (fire, theft, casualty), mortgage insurance, and other varieties. Since the insurance companies are still in business and seem to be thriving, many people are presumably insuring themselves against all kinds of calamities – the majority of which will never happen. But they do not care enough about their souls to insure themselves against the one thing that most certainly will happen: they must die, meet God, and give an accounting.” (The Parables of Jesus, pg. 116)

Jesus gives the spiritual parallel to the man’s worldly planning in verse 4 in what Jesus says in verse 9: “I tell you, make friends for yourselves by means of unrighteous wealth, so that when it fails they may receive you into the eternal dwellings.”

See, this parable is not about money per se, but it certainly does have implications for our relationship to it. As Jesus says in verse 13, “No one can serve two masters.” If your care for the future includes knowing that your bank account will one day forsake you whether you want it or not, then oh how that will impact how you use it for God’s eternal kingdom!

(Our kids get it – they have no bank account!)

III. He is Commended for His Quick & Decisive Action (vs. 6, 8)

“Take your bill, and sit down quickly…” (v. 6)

Seeing what needed to be done, the man took action right away and decisively, “For the sons of this [age] are more shrewd in dealing with their own generation than the sons of light.” (v. 8)

Do you want to utterly waste your life? Take the knowledge and revelation you have about who Jesus is, and just sit on it. Do nothing with it. Worship little. Bless no one. Cover your lamp.

You may have seen the news that John Shelby Spong died this week. Here is a man, a Bishop nonetheless, who had no Christian doctrines left to deny. And perhaps one of the saddest parts of his story is this: the secular, agnostic, unbelieving people that he tried to win over will soon forget that he ever lived. He wasted his life denying his own Lord.

On the other hand, do you want to be fruitful in this life? Then decisively, quickly come to the place where you know your merciful Lord, you bank everything (now and the future) on his grace, and you live everyday in sure hope that one day, you will see sure and certain fruit from that.

With that, we come to the end of our time together around this parable, but my hope is that you will take it with you. That you, fathers and mothers especially, will continue to feast on the Word of God. Don’t be afraid to not know the answer. Open up your mouth and keep the conversation going. Let me pray for you as you do.

A Collect for Holy Thought

O God, without whose beauty and goodness our souls are unfed, without whose truth our reason withers: Consecrate our lives to your will, giving us such purity of heart, such depth of faith, and such steadfastness of purpose, that in time we may come to think your own thoughts after you; through Jesus Christ our Savior. Amen.