What does John 16:26 mean?

Through the prophet Jeremiah, God predicted He would establish a new covenant with His people. This would replace the system of priests, temples, and sacrifices. The new covenant would be in the hearts of each individual person, allowing direct communication between them and God (Jeremiah 31:31–34). Hebrews chapter 8 further establishes how Christ is the fulfillment of this promised new covenant.

Jesus has promised His disciples that their understanding will drastically increase, after He is resurrected and the Holy Spirit has arrived (John 16:12–13). What was once spoken in vague proverbs will be made clear (John 16:25). The disciples have been commanded to pray "in the name of" Jesus (John 16:23–24). When they do so, through the indwelling of the Holy Spirit (John 14:16–17) and thanks to the reconciliation of Christ (1 Timothy 2:5), they will have direct communication with God. Discipleship with other believers will still be needed (Matthew 28:19; Acts 8:31), but those truths can be more directly stated.

The statement about asking the Father on the disciples' behalf can be interpreted in two ways. One is that Jesus means He "will not" make requests to God the Father, meaning they can ask Him directly. The other option is that Christ means that His requests on their behalf go without saying: something like "I don't have to tell you that…" Both have support from the surrounding context, though the idea of direct communication with God better fits the way Scripture describes the relationship between a believer and the Father (Matthew 27:51; Hebrews 9:8–12; 1 Peter 2:9).