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Tim Maas
In John 16:8, Jesus is speaking to the eleven apostles (those other than Judas Iscariot, who had left the company of Jesus and the other apostles in John 13:30) regarding the Holy Spirit (Whom Jesus had called "the Counselor" in the preceding verse (John 16:7), where Jesus had promised to send Him (the Holy Spirit) to the apostles after Jesus had ascended back to heaven following His crucifixion and resurrection). This promise was fulfilled in Acts 2 at Pentecost (fifty days after Jesus' crucifixion at Passover, and ten days after Jesus' ascension (Acts 1:9-11).
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