In the first few seconds we hear the word steward a number of times. So stewardship becomes the context for what is being said here. As father has told us over the last month as part of our stewardship drive, stewardship is a way of sacrificial living; giving time, talent and treasure back to God and for better use in the future. A sort of reinvesting of our things if you will.
First we see that the steward is being wasteful with what he has been given. This is the reason of his being dismissed as a steward. Having been caught out and made accountable, he contemplates a way out. A quick self examination finds that he cannot dig (hide) and that he is too proud to go begging in the streets. In trying not to cover his actions but rather to find a place of welcome, he becomes lenient in the debts owed to the master and in doing so he becomes what the Master wants us to be: merciful. And it is this astuteness, this deeper thinking (cunning) that becomes praised. This I think is the key to understanding this passage.
It reminds me of Mat 10:16 where Jesus sends his disciples out like sheep amount wolves so be as cunning as serpents and as innocent as doves. This is cunning.
Later, Jesus tells us to use money to win friends. He we see an image of right relationship with friends (a sign of the Kingdom of God). But these friends can give you access to eternity. Could these be saints and angels and all the heavenly host?
Jesus goes on to praise what the steward has done by making him an example of charity even though it is dishonest charity. The steward has been lenient with his masters money, not his own. Even so, this charity is praise worthy as he was not fixed on making money even for his Master.
Summing up, Jesus highlights that one cannot be the slave of two masters, and we have seen how far this steward went to stay a steward for his master. He went to great lengths to retain his stewardship. What are we willing to do to maintain right relationship with our friends and our closest friend Jesus?