Compare and contrast the challenges that Ray from Shoeless Joe and Santiago from The Old Man and the Sea face. What do these challenges reveal about each character?

The hero’s journeys at the heart of Shoeless Joe and The Old Man and the Sea have several strong parallels, despite more obvious differences. In both works, the author uses one apparent central theme, the human versus nature conflict, as a way to approach the actual core theme: the human versus themself. While Santiago is an old man who spends much of the novel alone and Ray is a young man who is often surrounded by family, each man embarks on a physical and spiritual journey that brings him back into touch with his own values. And, in different ways, each journey allows that man to make a contribution to his community.
Santiago and Ray both succeed in part because of their serious dedication to the task at hand. Santiago knows the sea, and in the past has been a renowned angler. His disappointment at not making a catch is accompanied by patience and respect, as he trusts that the sea will provide for him. Ray is also tightly bound to nature, as he has embarked on the daunting task of running a farm and then sets out to build the ideal ball field. To build it, he must apply himself to learning about grass and irrigation, deeply absorbing the lessons of nature. Santiago’s period of learning about the sea and his own inner resources is largely behind him, while Ray is just embarking on this dual journey to understand both nature and himself.
Santiago sets out to fish largely to provide sustenance for himself. He endures a period of failure before he reaches an enviable success. After 84 days of not catching any fish, on day 85, he lands a spectacular catch—really, the catch of a lifetime. Santiago respects the sea and understands that the giant fish is in one way the sea’s gift, and in another way is his reward for respectful interaction both with the sea and with the fish in particular.
Ray devotes himself to building the field both to bring his father and the White Sox to Iowa and to bring J. D. Salinger to him as a mission of healing for the author’s pain. He seems impractical where Santiago was practical, as he goes out on a limb to try something new and apparently foolhardy rather than just focusing on his farming. In the end, however, the men seem more alike than different.
For part of the story, Santiago has a companion, the young Manolin. After the boy’s father sends him to another boat, Santiago is alone on his mission. In this respect, Santiago’s story might be seen as diverging radically from that of Ray, who is surrounded by his family and is rarely alone. A likely parallel, however, exists between Manolin’s emotional support and provision of food and bait and J. D. Salinger’s support of Ray. Although Santiago is physically alone, he understands that Manolin is with him emotionally; Ray must persuade Salinger to go with him, but ultimately it is Salinger’s enthusiasm and insight that helps Ray achieve his goal.
Santiago spends much of his free time reflecting on memories, as he is already an old man, while Ray has his head in the clouds, and his visions may be real, or only seem real—he embarks on his quests because of the voices he hears. Santiago ultimately returns home without the fish, as it was all eaten by sharks. Ray succeeds at creating his dream ball park, so he might be considered successful where Santiago failed. Because Santiago has no family of his own, however, his emotional bond to Manolin is currently the strongest in his life, and he chooses to make him a gift of the fish’s sword. For Ray, the motivation he has to make his deceased father proud gives way to his realization that it is his relationship with his brother that matters. In both cases, the protagonists' achievements create closer bonds to significant people in their communities.