Hmm… I would disagree with a few of the things that were written here: the steward is neither a ‘loan shark’ (this would imply that the steward and the master were committing the sin of usury) nor is this a “debtor’s prison” situation (if it were debtor’s prison, then the debtors would have already paid out from all of their resources and yet still owe money; therefore, they have nothing to give, so giving a 50% discount would be meaningless – moreover, being broke after getting out of “debtor’s prison”, they would be unable to hire the steward, which is what he’s interested in, anyway!).
The parable is a difficult one to understand. In fact, scholars disagree on many aspects of the parable’s meaning. It’s important, though, to understand the context of the parable: beginning in chapter 14, Jesus is preaching on the proper disposition toward possessions. Having just told the parable of the prodigal son, which demonstrates God’s all-encompassing love for his children (even in the face of wanton spending and of begrudging filial devotion), Jesus turns his attention to the Pharisees. In the parable of the rich man and Lazarus, He implicitly accuses the Pharisees of love of money and of hardness of heart. Now, in chapter 16, Jesus turns towards his disciples.
The technical term for all of these sorts of parables is the “reversal of fortune” story. The prodigal son is a slave; he returns to sonship. Lazarus is destitute; he gains a place in the bosom of Abraham. The rich man is, well, rich (!), and he suffers the torments of Gehenna. In chapter 16, too, we have a reversal of fortune.
The rich man here is not necessarily a sympathetic character (nor is his steward). We see that the steward, acting on behalf of his master, has responsibility for managing his master’s finances. When we look at the values of the loans (800-900 gallons of olive oil and the amount of wheat that 20-25 family farms could produce in a season), we see two things: first, these amounts aren’t pocket change (in fact, they both amount to 500 days’ wages)! So, these people who owe the master are at least ‘businessmen’, if not roughly equivalent to the master himself! Second, we don’t know whether these are loans, properly speaking (‘give me X and I’ll pay you back 800 gallons of olive oil’) or if these are farming investments (‘give me the resources to grow olives and I’ll pay you back 800 gallons of the oil I produce’). Third, although the amounts appear to be unequal – that is, when the steward forgives the amounts, it appears to be favoritism – but that isn’t the case; in both examples, he’s forgiving the same monetary value. Finally, we need to look at what the steward’s actions are really doing, here, in order to understand the situation.
(Sorry I’m running long: let me continue this post…)