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I'm wondering whether, in the story of the Prodigal / Lost Son(s), Jesus probably intended the older brother to think of himself as a slave. This is for multiple reasons:

  1. V29: he says he has been slaving / obeying orders: "All these years I’ve been slaving for you and never disobeyed your orders."
  2. In the same verse he acts like his property still belongs to his father, "Yet you never gave me even a young goat so I could celebrate with my friends." This despite him already having received the property as his inheritance (v12) and his father confirming that it all belongs to him (v31).
  3. He is in the fields working (v25) rather than managing the estate. (More tenuous this one - is this a correct assumption?)
  4. He asks one of the servants what is happening (v25) rather than speaking to his family (father). (Again, more tenuous.)

If this is the case, it might be Jesus way of explaining to some of those listening (especially the Pharisees) that they were slavishly following the Law rather than behaving like sons of God.

Was this likely to be Jesus' intention with this character?

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I believe that the intention of Jesus is to hold up a mirror to the religious leadership, in effect saying, "Look, you're behaving as slaves but you're really sons. And, you're not the only sons. Others who you thought were 'out' are 'in'. Do not despise God's generosity (Matt. 20:15)." So, the elder son is not a slave but only acts and feels as one. It's an important distinction. The elder son, who by rights possesses all the father has, never acts like it! Marshall has some good comments on this in his NIGTC commentary (p. 612).

Your points 3 and 4 are tenuous. I'd look at v. 25 as managing the workers but since Jesus doesn't make anything of this, I wouldn't either. As far as him asking a servant rather than his father, this points back to his own feelings toward his father. Again, see Marshall.

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