Over the next several weeks he looked for work and visited with the Pages. While he maintained at public appearances during this time that he was determined to continue his court case till its end and attend the University of Missouri School of Law, in private he was becoming increasingly ambivalent. His mother said he had decided not to go, as they both believed it was "too dangerous". Nancy Page later recalled asking him directly about this. "His answer wasn't straightforward, and if I remember correctly, he said something like this: 'If I don't go, I will have at least made it possible for some other boy or girl to go.'"
In his last letter to his mother, dated March 3, he expressed similar sentiments:As for my publicity relative to the university case, I have found that my race still likes to applaud, shake hands, pat me on the back and say how great and noble is the idea: how historical and socially important the case but — and it ends ... Off and out of the confines of the publicity columns, I am just a man — not one who has fought and sacrificed to make the case possible: one who is still fighting and sacrificing — almost the 'supreme sacrifice' to see that it is a complete and lasting success for thirteen million Negroes — no! — just another man. Sometimes I wish I were just a plain, ordinary man whose name no one recognized.
He had begun the letter by telling her that he had come to Chicago "hoping to find it possible to make my own way" and ended it "Should I forget to write for a time, don't worry about it. I can look after myself OK".
He also wrote that his accommodations at the Y were paid through March 7, and if he stayed in Chicago after that he would have to make "other arrangements". After that, brothers at an Alpha Phi Alpha house took him in. He continued to have dinner at the Pages'.
Nancy Page said he told her he had taken a job at a department store. A reporter later found that although he had been hired, he had never reported for what would have been his first day of work. In the last days she had contact with him, Page said he seemed "to be running away from something." Gaines family members and descendants believe he and possibly the family as a whole had received death threats, and given their background in rural Mississippi would have been too fearful to report them to the police.
Gaines' financial needs continued. The Alpha Phi Alpha brothers took up a collection for him. He promised the Pages that he would repay their generosity by taking them out to dinner on the night of March 19, but he never did. Earlier that evening, he told the house attendant he was going out on a cold, wet evening to buy some stamps. He never returned, and no one ever reported seeing him again. His ultimate fate remains unknown.
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