ESV - 6 When Jesus saw him lying there and knew that he had already been there a long time, he said to him, "Do you want to be healed?
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Perhaps the man after being crippled for 38 years had given up hope of ever being healed, or maybe he was afraid that if he were healed he would not be able to get a job that paid more than begging since he had had no training as a child like other men had had. It is interesting that there was a "great multitude of sick, blind, lame and paralyzed people waiting for the moving of the water" and here was Jesus walking through this crowd headed for one single man whom He healed. Only one man was healed. Apparently this was the only person in that entire multitude that had enough faith in Jesus to be healed so Jesus healed him. I wonder if several others also had similar faith if Jesus would have healed them too.
My opinion is that Jesus knows what we want--but! He knows the person, himself or herself, needs it to be clarified. Example: We do not give others something unless they ask for it. (Unless it is a gift) In other words, Jesus was showing us how it needs to be done. He was being man so He could apply Holy Spirit's help.
The obvious thing is that Christ wants to direct the man’s attention to his need and the fact that it’s never been resolved. And that shows that He cares. Nobody else around there was compassionate. Nobody else was making sure he got in 1st or at all. It was a man who had lived almost 40 years without any mercy from anybody, even people who were miserable themselves. But now for the 1st time, here’s Somebody who is concerned about him. This is the compassion of Jesus. A stranger feels sadness for his misfortunes. A stranger? He's spreading a kind conversation with him! Keep in mind that this man by virtue of/because or as a result of his illness over this amount of time is considered a pariah/social outcast (i.e. he was marginalized or treated as insignificant or peripheral) by the Jewish leaders because they would believe this is punishment from God because this is man is bad. Nobody of any importance spiritually would have spoken to this man. https://www.youtube.com/watch?v=ntuUN0Lg1Es
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