What does Luke 16:1 mean?

Jesus continues His training session with the disciples during His gradual journey to the cross, sometimes called the "travelogue" of Christ (Luke 9:51—19:27). Scripture does not say exactly where or when this occurred. The chapter may have encompassed a single event since the Pharisees "heard all these things" (Luke 16:14). Or Jesus may have taught similar lessons several times and Luke is speaking in general.

The parable of the dishonest manager is among the most difficult to interpret (Luke 16:2–8). Most confusing is that the rich man seems to praise the manager for defrauding him. Jesus' use of this as an example is likewise easy to misinterpret. As with most parables, the key is not to overcomplicate the intended message. This strange story has a simple enough application: people of the world are cunning and know how to take advantage of the times in which they live. So, God-followers should use that same cunning in service to His kingdom.

The relationship between the owner and the manager is not explained in detail. The owner may not live on the property the manager stewards, since he doesn't know fraud is occurring until he hears from someone else. The manager's status as slave or servant is unknown, but he is used to working non-physical jobs (Luke 16:3).

The manager must have had some freedom to work without being supervised. He also seems to have no remorse when the owner finds out he has performed his job poorly. It's unclear what exactly it means that he was "wasting [the owner's] possessions." The owner plans to fire the manager, rather than having him arrested for theft. It may be that in areas where he did not expect to be monitored, he was just lazy or incompetent.