The Sermon on the Mount begins with the Beatitudes. The first beatitude from Jesus is as follows: “Blessed are the poor in spirit, for theirs is the kingdom of heaven” (Matthew 5:3). Jesus begins by acknowledging the “blessedness” of the poor.
This seems a strange way to start the sermon (Jesus probably wouldn’t have gotten an “A” in a homiletics class for this introduction). Nevertheless, it is interesting. Why does Jesus start off with the “poor?” Because only those who recognize their poverty (spiritually) will trust Christ and enter the kingdom of heaven.
Jesus was not speaking to economically poor people (although there are certainly economically poor people who are “poor in spirit” and for Jesus’ description here). Instead, He is talking to those who are “poor in spirit,” or those who humbly recognize their spiritual poverty and need for grace. It is those who recognize their spiritually destitute position who will humble themselves, turn from sin (repent), and believe the gospel (faith).
Here is the question: are you “poor in spirit?” Do you recognize your spiritual poverty and the need for God’s grace? Do you understand that you are spiritually broke and needed Jesus to pay the price you could never pay? Only those people will enter the kingdom of heaven. They are the ones who are truly blessed.