Why does fetching J.D. Salinger seem impossible for Ray in Shoeless Joe?

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The premise of having to "ease Salinger's pain" is challenging, to say the least.  One reason why this is so difficult is that the message is so very vague.  At the time, Ray only assumes that it is Salinger's pain and has very little evidence with which to work.  He knows of Salinger's love of baseball and the impact the closing of Polo Grounds had on him, but there is little other substantial evidence to indicate that Salinger is in pain. This is enhanced when Salinger claims to not have any pain.  In fact, little seems to suggest that Salinger is in much pain other than his desire to no longer write.  We perceive, like Ray, that something agonizes him, but it is hard to "ease his pain," when it cannot be clearly identified.  The magical realist style of the work prevents any clear delineation of this.  In terms of the challenges Ray has to face in bringing Salinger into his fold, the fake kidnapping, travelling across country, and convincing Salinger of the authenticity of his beliefs are the major challenges Ray has in this realm.  In a larger sense, the notion of "ease his pain," is a theme that can actually apply to many others in the novel.  Obviously, Shoeless Joe and the banished White Sox players, Moonlight Graham, as well as Richard and John, and the notion of Cubs fans in general can be but a few of the sources whose pain need to be eased along with, if applicable, Salinger's.  It is interesting to note that Kinsella identified Chicago sports teams as ones who pain needs to be eased.  Only at 2005, when the White Sox won the World Series, was their pain healed.  As for the Cubs, Kinsella knows that their pain is still yearning to be healed.

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