For us to understand this Beatitude, it’s important to understand who Jesus is referring to. Meekness isn’t something that should be pursued. It’s meekness that happens to a person.
The “meek” Matthew refers to are the Others. The oppressed, the marginalised, the people born into the “wrong” families. But, for these people, Jesus has good news. For those of us who are privileged, this is a confrontation to our position and a challenge to see others differently.