Consider again the context of Jesus’ ministry: facing opposition from the religious authorities for His denunciation of their religious hypocrisy (Mat 12:22-45), His popularity among even His supporters had also begun to decline due to the perceived difficulty of His teachings (see Joh 6:60,66).  As a result, He began to withdraw with His remaining disciples, both by teaching in parables (Mat 13; cf. Mar 4:11-12,33-34), as well as in person to various regions around Galilee (Mat 14:13,34, 15:21,29) and then to Caesarea Philippi (Mat 16:13).  Here, in spite of the fact that the Messianic kingdom Jesus proclaimed was not fulfilling his expectations, Peter made his great confession that Jesus was the promised Christ.  At this point in His ministry, Jesus “began to show His disciples that He must go to Jerusalem, and suffer many things from the elders and chief priests and scribes, and be killed, and be raised up on the third day”, (Mat 16:21).  Following the transfiguration (Mat 17:1-8) as an assurance and testimony of the superlative glory of the kingdom He proclaimed, Jesus especially began focusing His teaching on the nature of the humble Christ’s kingdom, and how it contrasts with the carnal, worldly expectations of men (see Mat 18:1-3,10-14, 21-22, 19:9,14, 23-25).  He further withdrew entirely from Galilee “into the region of Judea beyond the Jordan” (Mat 19:1) and has just now left there (Mar 10:17) on His way to Jerusalem (Luk 18:31) for the Passover where He will be crucified.  In the context of the rich young ruler’s question about obtaining eternal life Jesus has just spoken about the reward of His followers (Mat 19:28-29).  What does He then add in regard to their reward?  See Mat 19:30.  What does this hint about how their reward for following Christ may also be contrary to their expectations?  What are their expectations?  On what two other occasions had Jesus just recently taught something very similar but in a different context?  See Mar 9:35, Luk 13:22-30.

From a careful reading of Scripture, why should we not be surprised that in God’s kingdom “many who are first will be last, and the last first”?  I.e., what examples do we have illustrating this paradox that turns our human expectations upside down?  See Gen 17:18-21, 25:21-23, 48:13-19, Deut 7:6-7, Jdg 6:15, Luk 14:7-11, 15:11-32, 1Co 1:26-29, 15:8-10, Gal 2:9,11, Eph 3:8.  What does this indicate about how contrary our natural understanding in our fallen state is to God’s ways, and hence how far we really are from God and His kingdom?  Cf. Isa 55: 8-9.  If we are ever to be saved into God’s kingdom, will it ever be because we finally figure out on our own the wisdom of God for how we are to understand the true nature of things and the manner by which we are to conduct ourselves in the world so as to really lay hold of the abiding rest and peace and joy that alone can be described as eternal life?  If we are ever to be truly saved, by what means only will we be saved?  See Mat 19:25-26, Eph 2:8,9.  What does this remind us about God’s ultimate sovereign role in man’s salvation?  See Joh 6:44-45,64-65, 2Ti 2:25-26 for both God’s sovereign role and man’s responsibility in salvation.