Why does Jesus bless the poor in spirit?

Blessed are the poor in spirit, for theirs is the kingdom of heaven. –Matthew 5:3

Blessed are you who are poor, for yours is the kingdom of God.   –Luke 6:20

Jesus begins the Sermon on the Mount with eight remarkable beatitudes. The first is the most important because it introduces the other beatitudes and puts them in their proper context. And the first beatitude is distinctive in another way: while the other beatitudes speak of being filled with something, the first one is about becoming empty. God cannot fill us with his Spirit if we are already filled with something else.

The Beatitudes

Blessed are the poor in spirit, for theirs is the kingdom of heaven.
Blessed are those who mourn, for they shall be comforted.
Blessed are the meek, for they shall inherit the earth.
Blessed are those who hunger and thirst for righteousness, for they shall be filled. Blessed are the merciful, for they shall receive mercy.
Blessed are the pure in heart, for they shall see God.
Blessed are the peacemakers, for they shall be called God’s children.
Blessed are those who are persecuted because of righteousness, for theirs is the kingdom of heaven. Blessed are you when others insult you and persecute you and speak all kinds of evil against you falsely on my account. Rejoice and be glad, for your reward is great in heaven, for so they persecuted the prophets who were before you.
Matthew 5:3–12

Blessed are you who are poor, for yours is the kingdom of God.
Blessed are you who are hungry now, for you shall be satisfied.
Blessed are you who weep now, for you shall laugh.
Blessed are you when people hate you and when they exclude you and insult you and slander your name, on account of the Son of Man! Rejoice in that day, and leap for joy, for behold, your reward is great in heaven; for so their fathers did to the prophets.
Luke 6:20–23

Jesus begins the sermon with a series of paradoxical statements that are both shocking and memorable. But his pronouncement of who finds favor in God’s eyes confuses the crowd–Jesus’s words are contrary to what they have been taught all their lives. The people of Israel believe wealth and power are signs of God’s approval, but Jesus paints a radically different picture. He blesses those who depend solely on God and condemns those who trust in themselves.

The Good and Beautiful Life

When taken at face value, the Sermon on the Mount is opposed to much of what passes for Christianity today. The lifestyle Jesus prescribes is incompatible with the kind of life most Christians want to live. Church history tells a two-thousand-year-old story of how the sermon has been manipulated, marginalized, and ultimately neutralized. Karl Barth, the twentieth century’s most influential theologian, echoed Martin Luther (the sixteenth century’s most influential theologian) when he said, “It would be sheer folly to interpret the imperatives of the Sermon on the Mount as if we should bestir ourselves to actualize these pictures.”