In the previous chapter Jesus had been speaking primarily to the religious leaders. He continues this theme because "tax collectors" and "sinners" had been gathering around Him. These people were considered the lost of Israel, outcasts. Tax collectors were despised for two reasons. They worked for the occupying power, and they took their own cut from the people as well. Sinners were those who paid no regard to the Law, including adulterers and robbers amongst their number. So the Pharisees were shocked that Jesus welcomed these people, and saw this as an excuse to get at Jesus.
So Jesus tells them the parable of the lost sheep. The good shepherd goes out to seek for the lost sheep, He does not just abandon it. Moreover, when He finds it He cares for it and is full of joy. So if anyone turns to Jesus and is willing to be helped and restored by Him then God rejoices, and He delights in the fact that this lost sheep has been found.
The reference to the ninety nine sheep is probably ironic. All of us need to repent, the problem is that many of us think that we don't need to. Someone who feels terrible but knows their need of God is far closer the kingdom of God than someone who is satisfied with life and themselves and thinks that they do not need God.
Jesus then backs up the message with a related parable, this time about a woman who searches for a lost coin.She puts great effort into doing this and is delighted when her mission is successful. The kingdom of God is about calling people to repentance.
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