What are Jesus’ foundational teachings that lay the groundwork for discipleship in the church today? Within this paper, I will seek to work through the initial section of Jesus’ Sermon on the Mount to distill the essential theological lessons of Christ on discipleship. After introducing some important cultural realities concerning the state of discipleship in the church today, Matthew 5 will be thoroughly engaged. Beginning with a discussion on cultural, literary, and theological backgrounds, the passage will be broken down section by section to discern key truths expressed for the modern church. The paper will conclude with further reflection questions for church leaders as they seek to practically apply this teaching in their setting