CONTEXT from BibleRef.org:
Matthew 5 begins what is known as Jesus’ Sermon on the Mount. The size of the crowds following Jesus by this point in His ministry has become massive. People come from great distances in every direction to see His miracles of healing and hear His compelling teaching.
The crowd includes Jesus’ chosen disciples, His committed followers, and likely some who were simply curious. The sermon itself may have been much longer than what Matthew includes in chapters 5—7. Matthew’s call by Christ is explicitly described in Matthew 9:9, but ancient writing was not concerned with keeping events in strict order of time. Matthew’s call might have happened during Jesus’ ministry just prior to this speech (Matthew 4:23–25). This means Matthew may have been present for this message. As a tax collector, he would have been fluent in reading, writing, and keeping records. That opens the possibility that this is a word-for-word transcription of Jesus’ sermon. Even if Matthew compiled this from Jesus’ later repetitions, the words are still surprising, even confusing, and challenging (Matthew 5:2).
Matthew’s reporting of the sermon begins with a list of sentences called the Beatitudes. That name comes from the Latin word beatus, which means “blessed” or “happy.” Each sentence begins with the words “blessed are.” Blessed, as Jesus uses it here, means something like “having a good result or outcome.” It does not refer to feelings of happiness—in fact, some of these statements involve pain and suffering. Reading from a merely human perspective, it is surprising to hear the kind of people He mentions are “blessed.” Human nature doesn’t associate humility and mourning with good outcomes. Jesus’ entire sermon, though, is designed to show those who listen that our “normal” perspectives are upside down. What matters most is humility and the kingdom of God. These attitudes are reflections of those who understand God’s will and His perspective (Matthew 5:3–12).
You can look up the entire series on the Beatitudes by typing in, The Beatitudes by Thomas Watson into the search block in the upper right corner. Or you can look at those specific to meekness below.
If you look up the word meekness in just about any dictionary it says something to the effect: the quality or state of being meek: a mild, moderate, humble, or submissive quality. That definition is what most folks have in mind when they think or assume all “Christians” need to be; easygoing pushover.
Yet if we compare the word origins which is needed for a proper Biblical/Christian Worldview, nothing could be further from the truth. Christ is saying we will be happy and blessed, we need to be kindhearted and humble, and above all, we need to be self-controlled.
The last one may be the hardest for many of us. Maybe you are like me a grizzly old veteran whose type A take-charge personality just begs to explode. Or maybe you have a problem with not knowing when to be quiet and just do your job without comment. Before I was a Christian I used the acronym STD for Stop Think Do, now I use the acronym WWJHMD for What Would Jesus Have Me Do (I am not God so WWJD just does not work for me)? Does He want me to speak up, does He want me to intervene I must always remember even if the answer is YES, to do so with humility and respect.