Matthew 5:1-5

Rachel Workman: 5 One day as he saw the crowds gathering, Jesus went up on the mountainside and sat down. His disciples gathered around him, 2 and he began to teach them.

3 “God blesses those who are poor and realize their need for him,
    for the Kingdom of Heaven is theirs. God blesses those who are poor. Poor in what? Poor in spirit. When we admit that we are sinful and cry out to Jesus to be saved we are 'poor in spirit'. Those who are self-righteous and "rich”, cannot be saved. But those who realize their need for Jesus will inherit the Kingdom. It doesn't say those who are perfect and without sin. It says those who are poor and realize their need for him.

4 God blesses those who mourn,
    for they will be comforted. It's the kind of comfort that can be trusted. We look for comfort in many things. But to be comforted by our Lord surpasses all other comfort. It's comfort with a promise if that makes sense.
5 God blesses those who are humble,
    for they will inherit the whole earth. That's an area I need to improve upon.

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John Burnett:  5 When Jesus saw the crowds, He went up on the ^[a]mountain; and after He sat down, His disciples came to Him. ² He opened His mouth and began to teach them, saying,

³ “^[b]Blessed are the ^[c]poor in spirit, for theirs is the kingdom of heaven.

⁴ “Blessed are those who mourn, for they shall be comforted.

⁵ “Blessed are the ^[d]gentle, for they shall inherit the earth.  The sermon of all sermons and Jesus starts it out with how blessed the humble will be.  Humility is not a strength of mine and I struggle with self-righteousness.  Being poor in the spirit is realizing our spiritual depravity and that we have nothing good to offer God.  We have to fully rely on Jesus Christ and His Sacrifice and we are then imputed his righteousness and He is rich in the spirit.

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 Allen Michaels:  5 Now when Jesus saw the crowds, he went up on a mountainside (Which afforded room for all and where, addressing them from his height, he could be seen and heard by great numbers.) and sat down. His disciples came to him, ² and he began to teach them. None will find happiness in this world or the next, who do not seek it from Christ by the rule of his word. He taught them what the evil that they should detest was, and what the good they should seek and abound in.

 He said: 

³ “Blessed are the poor in spirit,
    for theirs is the kingdom of heaven.

With this phrase, "poor in spirit," most likely Jesus was speaking of our spiritual condition of poverty—the recognition of our need for God. "The kingdom of heaven" refers to people who acknowledge God as their King.

⁴ Blessed are those who mourn,
    for they will be comforted.

"Those who mourn" speaks of those who express deep sorrow over sin, or those who repent from their sins. The freedom found in the forgiveness of sins and the joy of eternal salvation is the "comfort" of those who repent.

⁵ Blessed are the meek,
    for they will inherit the earth.

Similar to "the poor," "the meek" are those who submit to God's authority, making him Lord. Revelation 21:7 says God's children will "inherit all things."