Shigechi first caught Josuke's attention when Josuke spotted some of his Stand, Harvest, collecting coins around town. Suspicious of a potential enemy Stand user, Josuke decided to investigate. What he found was just a high school kid running a one-man operation—gathering loose change with his tiny Stand duplicates and hoarding it all for himself.
When Josuke and Okuyasu approached him, Shigechi tried to win them over by offering to share his earnings, apparently thinking this would make them friends. The two weren't impressed by his obvious desperation or his complete lack of common sense. Josuke actually pushed back against just taking advantage of him; instead, he suggested they pool their efforts and split everything three ways fair and square. Seemed reasonable, right?
Wrong. The moment Shigechi realized Josuke and Okuyasu expected an equal cut, he flipped. Being called an idiot wounded his pride, and the idea of sharing the money genuinely offended him. He bolted, and what followed was a chaotic chase where Shigechi showed he wasn't completely useless as a fighter. His real strength was that Harvest came in dozens of copies—he could overwhelm opponents with sheer numbers and dirty tricks. He even got creative with attacks, like having Harvest inject alcohol directly into their bloodstreams while they were trying to catch him.
Eventually Josuke and Okuyasu wore him down. Once subdued, Shigechi finally came to his senses and admitted they'd earned their share. The three actually ended up becoming friends at school after that.
Content compiled by AnimeList.moe from publicly available sources.