Viewed carefully, the parable in Luke 16 gives no indication that the rich man’s stable of contractors (‘debtors’, χρεωφειλετῶν) had been struggling in their operations. We only know that they had not yet paid. We have no indication whatsoever that these ‘debtors’ were unable to pay. Quite to the contrary, it is the steward who suggests fraud. Surely, if these on-site managers had wound up much below expectations, they’d not have self-reported such high levels of profit ‘in kind’.
The rich man's problem was that his steward did not know what each contractor owed. Naturally, therefore, neither did the rich man. That's the whole point of the situation, when the parable opens. It wasn't the rich man's job to keep up with which ones of his holdings were doing how well at all times. That’s why rich people have stewards. The top level managers are expected to manage the operational managers. But this steward was reportedly derelict in that duty. On examination, the steward’s alleged crimes of neglect were proved true when he could not summarize on-the-spot the details of those accounts he'd been given to oversee.
The steward hadn't yet been dishonest. He'd just been very lazy.
Much worse, by far, this steward had been horribly anti-social.
There was still plenty of good revenue to be had, but the on-site mangers most directly responsible for generating that revenue had been severely neglected. These good, faithful contractors were supposed to depend on this particular steward as their link to their landlord and patron, but the steward had been so absent for so long that he wasn't even aware of their bottom lines.
Such on-site managers could not have been comfortable hearing nothing for so long from the rich man whose property they'd been working. It may have even been one of these managers who first brought the poor steward's conduct to his master's attention. Yet, even still, these contractors were pleased enough with the way things had been going to self-report sizable debts. Remember, the landlord didn't know what they owed. The steward didn't know what they owed. But the on-site managers reported it happily.
Now the other shoe drops. These contractors must also have reported their own kickbacks to the client/landowner. After all, who else could have told him? Like the rich man paid heed to his wealthy friends first, these 'debtors' knew who was buying their bread in the long run. They were pleased enough to report their debts honestly, so they must have been prepared to pay as much happily. Therefore, it seems they did what the steward told them, sent as much as the steward had told them, and then also sent word to the rich owner about the details of their new deals.
This new report - surprisingly – is what finally pleases the master. The puzzle is – why?
To answer that, we need only sum up what we’ve already observed.
To be concluded…
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