It's often difficult for Jesus' followers to accurately convey to others his importance in their lives. If we regard him only as the founder of a specific religion, we don't have that problem. In that case, Jesus simply provides us with an institution which offers us the means to get into heaven. He's not someone who relates to us and we to him as a real person.
His earliest followers, including those who gave us our Christian Scriptures, had yet to experience an institution, as we know it, through which they'd filter their experience of him. They just had him, risen and alive, present in everything they did.
We've some inkling of how they valued his presence when we hear the early Christian hymn Paul inserts in our Colossians pericope. Listen to the different concepts which come to the author's mind and pen when Jesus is mentioned. ". . . Image of the invisible God, firstborn of all creation . . . head of the body, the church . . . the beginning, the firstborn of the dead . . . in all things, pre-eminent . . . in him all the fullness . . . making peace by the blood of his cross . . . ." No one has ever entered into the life of the Colossian community who has more drastically changed that community.
In our II Samuel reading we get a small glimpse of how Jesus' ancestor David was regarded by the people in the 10th century B.C.E. Originally David was king only of the southern half of the Promised Land, Judah. Saul's son, Ishbaal, was king of the northern half, Israel. The latter eventually was assassinated. That's when the elders of those 10 northern tribes "came to David in Hebron" and asked him to lead their nation also.
Scholars tell us the best thing David had going for him was his unifying personality. Though an adulterer, a murderer, and, without doubt, the worst parent in Jewish history, he could unite the 12 disparate Jewish tribes and all other factions, molding them into one nation. This unifying dimension of David's personality seems to have prompted the blind Jericho beggar Bartimaeus to cry out, "Jesus, son of David, have pity on me!" The good which David brought to all Jews is what Bartimaeus expected Jesus to bring to his life.
We see some of the significance people attached to Jesus in today's gospel passage. He certainly didn't fulfill everyone's messianic expectations; else he wouldn't have had to endure these Golgatha taunts. But he did make a difference for some. In this situation especially, for the thief who asks, "Jesus, remember me when you come into your kingdom."
His request and Jesus' response is even more significant when we know the history of the community for which it originally was written.
Christians at first believed Jesus would return quickly after his resurrection and escort his disciples into heaven. At that time, the question most asked was, "What will happen to those who die before Jesus' return? Do they lose out on the heavenly goodies?" In I Thessalonians, Paul assures his readers that those who die before Jesus comes back will simply spend the interval in the grave, biding their time until that glorious occasion arrives, then they'll be the first to rise.
Thirty years later, when Luke writes, Christians are facing a crisis in faith. Jesus not only hadn't returned, there was no sign he'd do so in the near future. Luke is the first Christian author to dump the "time in the grave" belief and reach the conclusion that Christians who die receive their own personal Parousia. At the moment of death, they instantly find themselves in heaven with Jesus. That's why Luke's Jesus can assure the thief, "Today you will be with me in Paradise!" (Were this scene in Mark or Matthew, Jesus would have said, "After a brief period in the grave you will be with me in Paradise!")
The risen Jesus' personality obviously triumphed over "church doctrine." Only someone who had a deep relationship with such a living person could have dared take such a drastic step.