This thesis examines verses 7-15 in Chapter 16 of the Gospel of John to see if what Jesus said specifically describes the pivotal role of the Holy Spirit in triumphant Christian discipleship in a hostile world throughout the Christian era. The key words Sympherō and Paraclete are capable of translation in different ways, and each different rendering changes the significance of the chosen passage. This is examined in both its historical and literary context, as these have a significant impact on the meaning of the passage. The preferred translations ‘advantageous’ and ‘a strong person coming alongside, someone to help in times of trouble, someone summoned to give assistance’, have a deep relevance for our understanding of the pericope, Jesus’ last teaching to His disciples, on the role of the Holy Spirit to believers in a hostile world, and its application to our own situation.