Over the next several years, Walcott fought in dozens of matches, winning most of them but losing occasionally. However, boxing failed to provide a dependable source of income. After he married and started a family, Walcott was forced more and more to take jobs outside the ring to make ends meet. His ring career took a positive turn after the unschooled Walcott began to work with trainer Jack Blackburn, who helped to teach him more about the art of boxing. His association with Blackburn ended abruptly when the trainer received an offer from a couple of gamblers to come to Chicago to train an amateur champion named
Joe Louis. As a condition for accepting the job, Blackburn wangled an invitation for Walcott to accompany him and join the gamblers' Chicago stable of fighters, but Walcott came down with typhoid and was unable to make the trip.
Without Blackburn's guidance, Walcott's boxing career once again seemed to lose direction. He continued to box when he could but was forced increasingly to work at low-paying jobs outside the ring to support his family. Walcott began to lose hope. Then came a call from Blackburn, telling him that Joe Louis, training for a fight with Max Schmeling, was looking for sparring partners. Walcott eagerly headed for the Louis training camp, but on his very first day on the job, he dropped Louis with a left hook, abruptly ending his stint as sparring partner.
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