According to Bailey
Bailey assumes that the parable was told only once and argues that the account in Luke is the original one. His argument against an alternative view that Matthew is closer to the original and that Luke is secondary is extensive.
Concerning the setting of the parable in Luke, Bailey is concerned to stress the importance of “table fellowship” and has an extensive quote from Jeremias in a work not cited in this blog. Part of that quote reads, “To understand what Jesus was doing in eating with ‘sinners’, it is important to realize that in the east … to invite a man to a meal was an honour. It was an offer of peace, trust, brotherhood and forgiveness.” Bailey himself writes, “In the East today, as in the past, a nobleman may feed any number of lesser needy persons as a sign of his generosity, but he does not eat with them. However, when guests are ‘received’ the one receiving the guests eats with them. … Jesus is set forth in the text as engaging in some such social relationship with publicans and sinners. Small wonder the Pharisees were upset.” He also argues that not only might Jesus have been eating with ‘sinners’ but that he himself had been hosting ‘sinners’.
In accordance with what one expects from Bailey, he sees a precise structure to the text, beginning with “What man …” and ending with “… who need no repentance”. The structure he perceives is chiastic, with the centre piece being, “And coming to the home he calls to the friends and neighbours”. And on each side of this centre piece there is a reference to “rejoicing”. One should note, that in order to discern the chiastic structure that he proposes he has to include the words that Jesus uttered that followed the parable.
Bailey claims that while in the Old Testament “the figure of the shepherd was a noble symbol … the flesh-and-blood shepherds who in the first century wandered around after sheep were clearly … unclean. … It is difficult to know how the rabbis managed to revere the shepherd of the Old Testament and despise the shepherd who herded the neighbour’s sheep … But this seems to have been the case.” Furthermore he writes, “It can be seriously questioned whether any Pharisee would ever take up the task of a shepherd under any condition. Thus the decision to address Pharisees as shepherds is a culturally and theologically conditioned decision of some significance.”
Concerning the parable itself, Bailey claiming that in the case of his shepherd friends, in his day and age, a shepherd in charge of 100 sheep would most likely be hired by one or more people, 100 sheep either being an indication that their owner was quite wealthy or that a number of families had made of their sheep one flock, the average family only owning five to fifteen animals. Transferring this understanding to the time of Jesus he argues that the shepherd in the parable does not necessarily own the sheep. This possibility does not seem to have occurred to Kistemaker who has a different view on what it would mean for a man to own a hundred sheep and accepts Bishop’s view that such a man would be one of small or average means. Perhaps Bailey is in error in supposing that what the situation was like in the twentieth century applied to what it was like in the first century A.D. However, Bailey, with his perspective, that the man would most likely be someone who was hired, argues that the man would not necessarily be a hireling but rather someone from an extended family which would explain why the community is so glad upon the lost sheep having been found. What would have been a loss for the shepherd would have been a loss for them.
Bailey believes that the reference to the rejoicing by the shepherd is not true to form. “The natural thing for the shepherd of the parable to have said would be, ‘I have found my sheep.’ Instead we have a … climax on ‘joy of restoration’”. Again, referring to the need to carry the lost sheep, now found, over a long distance, he writes “Surprisingly, this shepherd rejoices in the burden of restoration still before him.” His point seems to be that the oddity is something purposefully inserted into the parable, being consistent with, from his analysis, the matter of “rejoicing”, which brackets the centre piece of the account, and thereby being of considerable significance.
He also recognises two matters which the reader or listener may see as problems. Firstly he says that one might expect a passive phrase, such as “‘if the sheep was lost’ which would exonerate the shepherd from any blame. Rather the shepherd is clearly assumed negligent in his duty as a shepherd. He ‘loses’ the sheep.” Bailey seems to assume that in his telling of the story, Jesus wants the hearer to recognise that the shepherd has been at fault.
Secondly, the association of “the wilderness”, where the sheep are left, with “the house”, to which the shepherd returns, might seem odd. As part of his rationale for what he believes would have occurred in real life, Bailey writes, “The roving tribesmen keep sheep in the open at night. Peasants, living on the edge of the pasture lands, bring the sheep to the courtyard of the family home at the end of each day.” That there is a reference to “coming to the home” or “coming to the house” suggests to Bailey that a peasant shepherd is in mind. He then refers to a possible scenario, quoting at length from Levison. The scenario is that in the situation being portrayed, there would have been a number of shepherds involved in the caring of the flock and they would form part of that community which would be overjoyed upon one of the shepherds returning with a sheep that had been lost. Levison, referring to his own observations made in relatively modern times, writes, “Two and even three, shepherds are commonly employed. When one sheep is lost and the shepherd goes to seek it, the other shepherd takes the flock home. On arrival, the neighbours would at once notice the absence of the shepherd or they would be told of it, for apart from the possibility of the loss of the animal, it is often a question of the safety of the man. Should he encounter a wild beast, a single-handed shepherd, with only his stick and sling, is in a perilous predicament. The finding and brining home of the lost sheep is therefore a matter of great thanksgiving in the community.” Bailey appeals to his own observations to indicate how natural it would be for a shepherd to celebrate with his friends in a situation similar to the parable by saying that, “Village men gather almost nightly to discuss the events of the village, recite poetry, and tell stories from the oral tradition.”
However his appeal to Levison’s belief that there would have been more than one shepherd involved could be seen to be at odds with his argument that one shepherd, whatever his relationship to those who owned the sheep, would have been in charge. In seemingly endeavouring to avoid this difficulty he writes, “I am told by Palestinian shepherds that no man can care for a hundred sheep permanently by himself. He has no feed for the sheep. They must be led out each day. No man can count on perfect health 365 days a year (not to mention his family and community duties).” But in the story that Jesus tells, the reference is to a single occasion. It could be that Bailey in providing his understanding of what probably lies behind the story, however interesting, has gone too far. Although one of the problems might be that practices “now” and “then” might differ considerably, we also need to recognise that the story that Jesus told is short on details. In fact Bailey recognises that as told, the parable itself says nothing about what happened to the 99, apart from their being left in the wilderness. One might also add, that among other things, the story knows of only one shepherd!
 For Bailey’s section on the parable and its setting see Bailey, K.E., Poet & Peasant and Through Peasant Eyes, combined edition, Eerdmans, Grand Rapids, MI, 1983, pp. 142 – 156