Regarding the danger and severity of the older brother's sin, Keller writes:
Elder brothers don't go to God and beg for healing from their condition. They see nothing wrong with their condition, and that can be fatal. If you know you are sick you may go to a doctor; if you don't know you're sick you won't - you'll just die.
... Pride in good deeds rather than remorse over his bad deeds, was keeping the older son out of the feast of salvation.
Lord - I don't want to die. I need your forgiveness, your healing, and your life. This however is the same need as the younger brother who is also in rebellion. The younger brother, in his own self-righteousness flinches at the slightest hint of correction or confrontation. They see surety and confidence as arrogance and legalism. Younger brothers are while excel in understanding and seeing brokenness and thereby receiving and bringing healing. In doing so however they tend to run from anything that hints of righteousness and proper living.
I think both brothers need and can benefit from the other but sadly too often their reaction to each other pushes them further into their rebellion.
As a side note, one final "ah ha" from Keller in regard to this story. Who should have gone after the younger brother? In the other parables of Jesus recorded in Luke 15, someone went after that which was lost but had great value. In the story of the prodigal son/father, no one pursued the younger son. In his pride, the older brother failed in his role of older brother. It is he that should have abandoned all to lovingly find the younger brother to return him to the father so that both could rejoice in the salvation feast.
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