What does “blessed are the meek” mean (Matthew 5:5)?

from the old testament

• Matthew 5:5 echoes Psalm 37:11, which says, "But the meek shall inherit the land and delight themselves in abundant peace." This holds true for life on Earth and for life in eternity.
• The well-known Proverb 16:18 warns that "Pride goes before destruction, and a haughty spirit before a fall." Many other Proverbs similarly teach the importance of humilty (Proverbs 11:2, 15:33, 18:12, 22:4).
• Moses was commended as "very meek" (Numbers 12:3). By contrast, other figures, such as King Uzziah, "grew proud" to their own destruction (2 Chronicles 26:16-21). God brought Nebuchadnezzar low because He was glorifying himself (Daniel 4:28-37).

from the new testament

• In the third Beatitude of the Sermon on the Mount, Jesus says, "Blessed are the meek, for they shall inherit the earth" (Matthew 5:5). The Greek word for "blessed" is  makarios, which means spiritually blessed. That blessing applies to life now and the life to come.
• Jesus is the ultimate example of meekness. Though He is God, He "emptied himself, by taking the form of a servant" and "humbled himself by becoming obedient to the point of death, even death on a cross" (Philippians 2:6-8).  He told His disciples that He came "to serve" rather than "be served," even washing their feet the night before He was crucified (John 13:4-11).
• Christ calls His followers to "walk in a manner worthy of the calling to which you have been called, with all humility and gentleness" (Ephesians 4:1-2).
• One of Jesus' key criticisms of the Pharisees was that they "love[d] the place of honor at feasts and the best seats in the synagogues" (Matthew 23:6). By contrast, Jesus taught in the Parable of the Wedding Feast that we should sit in the lowliest seat (Luke 14:7-11), and He told His disciples that "he who is least among you all is the one who is great" (Luke 9:48).

implications for today

"Not to brag, but . . . "

"I'm normally not one to sing my own praises . . . "

Self-promotion. It isn't something social media influencers invented. Human beings are prone to it, which is why the Bible contains so many exhortations about humility.

When you do a good deed, how many people know about it because you told them? Has your group Bible study participation become less about examining God's Word and more about impressing others with your knowledge? It's easy to notice self-importance in others but miss it in ourselves. Remembering some key truths can help, such as Jesus' words to the rich young man apply: "No one is good except God alone" (Mark 10:18). Jesus' actions were just as instructive: He washed His disciples' feet and suffered a humiliating death on the cross.

Defeating the sin of pride is a battle that we can only win through Christ's strength—-praying for Him to give us a servant's heart so we become more like Him.