THESE three verses are peculiar to Luke and are not found in the Sermon on the mount in Matthew's Gospel. They would be out of place in the Sermon on the mount, but are supremely comfortable in Luke's account of the Sermon on the plain, and fit into the context like a glove.
When we were considering verses 20 to 23 where Jesus was speaking of those who are blessed, we saw that Jesus was accounting blessed those who physically suffered from poverty, hunger, weeping and rejection from the world, and learnt that they were blessed because their suffering was because they were true disciples of Christ, and experiencing the rejection and persecution of the world because of their allegiance and witness to Christ and his gospel. They were blessed because they gave all their allegiance and love to Christ, whatever the cost in this life, and because of this they were those who were laying up treasure in heaven, and had a place in that glory reserved for them by Jesus. The blessedness was because they renounced comfort in this life and believed Christ's promise that there was a crown of righteousness for them in heaven.
These woes speak of the opposite way of life, and its consequences. The people described here are those who seek all their happiness in this life and in this world. They have chosen all this and disregarded Christ, and never think of death and what follows. These people live for this world, and never consider what will happen to them when they die. Usually, if they are challenged to consider life after death, they seem to have a sense that this life is not all that there is, and that there is an existence beyond this life, and with this in mind they have a complacent belief that the existence to come after death will be one of blessing. If they think of God they think of one who is always loving and will accept everyone, and they imagine life beyond the grave as being much similar to this life, but somewhat better. They consider the character of God to be love, and never have any thought of his holiness, and any idea of condemnation and eternal rejection by God is totally denied.
The Greek word translated as 'woe' has a twofold meaning. On the one hand it has the idea of grief, and so could be translated as 'alas'. On the other hand it has the meaning of denunciation, which has the idea of total loss and suffering. Both these meanings are present here. Jesus is expressing grief over these people, because he sees their eternal doom, and their total indifference to it, and unbelief in it. Jesus does not want them to suffer eternally, and has grief such as is expressed when he wept over Jerusalem because they rejected him and the salvation he provides. But there is also the pronouncement of an inevitable end in judgement which means that when Jesus comes again at the end of the world, they will be condemned to everlasting punishment in hell. It is such a pity and a sadness that the church today has lost the sense of grief over those who are lost and on the broad way which leads to destruction, because they have the spirit of the world, and do not truly from the heart come to Jesus for the gift of his heavenly and eternal rest.
The point Jesus is making in these woes is not that riches of themselves are wrong or bring eternal death, or that having enough to eat and enjoying some of the luxuries of life and being happy is wrong, but Jesus is expressing a condition of heart which looks to the pleasures and praises on this world as the goal in living, and lives for this world, and puts all the exertion of living into gaining this goal.
Jesus pronounces disaster for them, because such living ignores the needs of the soul, and leaves God out of their lives and ignores his claims upon them, and so do not seek the remedy for sin in Jesus, and so must suffer the condemnation of God on them because of their sin, and so end up in hell. He pronounces woe on them because they have all their reward here on earth, and so have had their heaven on earth, and lost heaven to come. Jesus pronounces woe upon them because for the relatively short time we have in this life, they have neglected the life to come which is eternal, and lost any riches, satisfaction, joy or praise from God and in his heaven.
The spirit of the world expressed in the life and aspirations of those Jesus grieves over is a life where this world is everything. They have their heaven on earth. Jesus expressed the same thought when he said, "What shall it profit a man, if he gain the whole world, and lose his soul."
When we look out on our society, which is expressed so vividly on TV, we see this spirit of the world. Everyone is looking for their 'pie' here in this life, and totally ignore eternity, and so they will have no 'pie' when they die. The grief is in the terrible suffering of hell which is revealed in the Bible.
We need to meditate deeply on these woes until we whose hope is in Christ are so moved with their plight as lost souls that we are moved to pray for them, and seek God for the grace to seek and to save the lost by witness to Jesus who came into the world to save the lost.