Dr. Tim Keller
The author of The Prodigal God, Timothy Keller, says on page 136 of his hard cover book, "I want to acknowledge a special debt to the work by Kenneth E. Bailey, Finding the Lost Cultural Keys to Luke 15 (Concordia, 1992) for many of the insights into the parable's cultural and historical backgrounds that I use in The Prodigal God."
This website is dedicated to Dr. Ken Bailey who lived and taught as a world renowned scholar in the Middle East for over 40 years. What follows are two points of difference between Keller's interpretation and Bailey's that may help you think more deeply about The Prodigal Son parable.
POINT #1 "Comes to senses" vs. "Comes to himself"
Keller indicates that the younger son "comes to his senses" as he faces starvation in the far country. Then he returns home as a repentant sinner to his father's joyful accepting arms. Yet, according to Bailey, the younger "comes to himself"--in other words, he relies on himself. In so doing, he crafts a plan where he will pay back the money as a skilled craftsman. Further the son crafts a speech to manipulate his father, not to repent. (The Pharisees know the scriptures well and known that Pharaoh used a similar speech to placate Moses to stop the plagues.)
Yet if the younger follows though with his plan he will likely, over time, become like his older bitter brother--remaining lost. It's only the father's costly demonstration of unexpected love that opens the younger's eyes to his own condition according to Bailey. The younger's journey home was solely motivated by his hunger pangs and fear of starvation. He did not consider his father's broken heart. As he came closer to his village, he expects to be greeted by his father's anger and the community's rejection, (kezazah ceremony.) Yet while he was a long way off, he sees his father running to him, (a shameful act to run and expose legs in the Middle East.) Then instead of slapping him, his father hugs and kisses him with great joy. Now, the son sees, maybe be for the first time, the great love his father has for him. It's a transformational moment, (metanioa).
In this parable, according to Bailey, Jesus redefines repentance. The son's repentance, in the far country, driven by hunger and motivated by fear will not allow him to see his father's broken heart and his need for reconciliation. In contrast, Jesus' definition of repentance is "accepting being found." Only as the son experiences his father's costly demonstration of unexpected love will he see his father's love for him and experience peace, shalom.
You may retort, wouldn't any parent to run to their child with open arms in this situation? Not so fast. Let's look briefly at the situation. It may have been different had the son said apon leaving, I love you father, but my dreams are carrying me from this village to the big city. I'll write often. No, the son wanted the his inheritance prior to his father's death. In the Middle East this is a clear message that he wants his father dead. Yet, the faher grants his son's request and bears the public shame and the hate of his son. Over time, however, the father transforms this anger into grace and compassion.
POINT #2 "True elder brother" vs. "Father"
Tim Keller indicates on p. 85 of his book, "There was no way for the younger brother to return to the family unless the older brother bore the cost himself."
In contrast, Dr. Bailey points out that the Father is able to receive the younger son home. From my perspective, this interpretation provides a better foundation in which the father represents Jesus, not the true elder brother.
From Dr. Bailey's, Finding the Lost Cultural Keys to Luke 15 (p. 116):
The Jewish law of inheritance is carefully spelled out in the Mishnah. The critical text is as follows:
R. Jose says: If a man assigned his goods to his son to be his after his death, the fatehr cannot sell them since they are assigned to his son, and the son cannot sell them since they are in the father's possession. If the father sold them, they are sold [only] until he dies; if the son sold them, the buyer has no claim on them until the father dies. The father may pluck up [the crop...] and give to eat to who he will, and if he left antything already plucked up, it belongs to his heirs (B.B. 8:7 Danby,377)
This text provides the legal framework assumed in the parable. The rabbi quoted is Jose ben Halafta (A.D. 140-65; cf Danby, 827). Thus the text is early and can be considered as reflecting the legal attitudees of the period. The assumption of the above text is clear. The father will (of course) initiate the discussion. The sons will have the right to dispose of the property only after the father dies. In the meantime the father can spend the income from the estate as he chooses. What the father does not spend is added to the capital. So in our story, the father at the end of the parable has the full right to butcher the (young) fatted calves. But if the father entertains infrequently and modestly, then the capital of the estate will gradually increase to the older son's eventual benefit. This is an important part of the tensions of the story at the end of the parable. But the legal description of the Mishnah noted above has no provison for the younger son pressing for a division of the inheritiance. No culture sort out legal precedence for social situations that will (naturally) never happen. If they do happen, they will be dealt with automatically. The wisdom tradition may offer some advice but laws are unnecessary. The boy (of course) will be thrased and denied his request. So the above Mishnah text indirectly heightens the unthinkable nature of the prodigal's [initial] request.