Why does Jesus predict misery for rich people?

But woe to you who are rich, for you are receiving your comfort in full. Woe to you who are well-fed now, for you will hunger. Woe to you who are laughing now, for you will mourn and weep. Woe to you when all people speak well of you, for that is how their ancestors treated the false prophets.
Luke 6:24–26

What sorrow awaits you who are rich, for you have your only happiness now. What sorrow awaits you who are fat and prosperous now, for a time of awful hunger awaits you. What sorrow awaits you who laugh now, for your laughing will turn to mourning and sorrow. What sorrow awaits you who are praised by the crowds, for their ancestors also praised false prophets.
Luke 6:24-26 (NLT)

Jesus opens the Sermon on the Mount by teaching his followers that what is commonly accepted as “the way things are” is not, in fact, the way things are. He offers a series of memorable sayings that redefine wealth and poverty, and he points to a day when a great reversal in fortune will occur–a day when the poor, persecuted, and marginalized will be lifted up, and the powerful, popular, and self-sufficient will be brought down.

Jesus describes this great reversal in terms of blessings and woes, and he divides all of humanity into two groups: the poor-in-spirit and the rich-to-themselves.

• Jesus describes the “poor” in terms of their new nature–the kind of person they become when they are filled with the power of God and led by the Holy Spirit. They will become humble, repentant, gentle, merciful, single-minded peacemakers who are intent on living in a way that honors God and loves others. Jesus’s apprentices will encounter injustice and undergo persecution, but they will also experience God’s blessings now and for eternity.
• Jesus describes the “rich” in terms of their shortsighted hedonism–those who choose to live apart from God and strive for worldly status may enjoy a time of comfort and prosperity, but ultimately they will be miserable and destitute. For them, Jesus says, only woe awaits.

The Greek word translated “woe” is omai, an exclamation of grief and pity. Woes are the heartaches and tragedies that come to those who make poor choices. But who is Jesus describing as rich, well-fed, laughing, and popular? They are the people at the top of the social pecking order. In ancient Jewish and Roman culture, wealth played a large part in one’s status, but other factors were also significant: gender (a woman’s status was usually attached to the social standing of her husband and/or father), family reputation (people rarely relocated, so the history of each family in town was well known), religious piety (how well one followed the prescribed religious rites and practices), education (those who could reason skillfully, write well, or deliver a powerful speech were revered), and occupation (some vocations, like rabbi, were highly esteemed; other jobs, like tax collector, were reviled).

As human history has revealed time and again, cultures based on such values produce the kind of people who put themselves first and treat others accordingly. Jesus is not condemning people for having money, eating well, and enjoying life. He is condemning an attitude that is often found in the rich, well-fed, laughing, and popular people of the world–the attitude of autonomy (self-rule). When Jesus pronounces woe on these people, he is not condemning them; he is warning them of a great reversal that is coming and exhorting them to change.

This great reversal was a popular theme in Jesus’s teaching. He often urged his disciples to learn humility because one day the last would be first, and he told them stories to reinforce his lessons. One of the most memorable is recorded in Luke 16. Jesus describes a rich man and a beggar who die on the same day. The rich man is depicted as self-satisfied and oblivious to the needs of the beggar who sits at his gate. When the rich man dies and asks Abraham for relief, he is told something similar to what Jesus is saying in the beatitudes and woes. Abraham tells the man, “Child, remember that you in your lifetime received your good things, and Lazarus in like manner bad things; but now he is comforted here, and you are in anguish.”

The woes and beatitudes describe two ways of thinking, two sets of values, and, ultimately, two eternal destinies. Jesus tells his apprentices to trust in God and to not be deceived by appearances. People who ignore God may enjoy a time of affluence and comfort, but their enjoyment will be short-lived. God’s people may experience times of poverty and persecution, but according to Jesus, a great reversal is coming.

Perhaps the most encouraging aspect of the beatitudes and woes is their broad scope. God’s blessings are available to anyone and everyone. Wealth and status are not necessary. In fact, they are often obstacles to faith. According to Jesus, all we need is the willingness to trust God’s Word and live by faith. A little later in the sermon, Jesus will say it this way: “Seek first the kingdom of God and his righteousness, and he will take care of all your needs.”

Next: Salt of the earth–light of the world.