Connie's gambling den story is firmly connected to Young Sheldon seasons 5 and 6, but one detail in Young Sheldon season 1 hinted at its development as early as episode 5. Medford's less well-kept secret was discovered by Pastor Jeff too in Young Sheldon season 6's finale, with the hurricane threat causing Connie to do the right thing and let every laundromat customer shelter in the secret gambling room. However, Connie's good deed necessarily unveils the truth of her seedy business to Medford's supposed moral figure, making Pastor Jeff the latest among Young Sheldon's relatively central characters to know about the gambling room and judge Connie because of it.
Connie's gambling room already caused a ruckus in Young Sheldon season 5 when she first opened it and involved Georgie, greatly displeasing Mary when she learned about it. Dale was also slow to accept Connie's entrepreneurial dabbling because he felt it robbed them of their time together and also because he didn't approve of the illegality of it all, even getting it unintentionally closed down when he asked his cop friend about it. Still, while the gambling story took center stage between Young Sheldon seasons 5 and 6, a considerable hint the gambling den would have been in Connie's future already appeared in Young Sheldon season 1, episode 5.
Indeed, Connie's gambling was introduced early on in Young Sheldon season 1, episode 5. When Sheldon started giving statistics-based pointers on how to strategically win football matches both in general and to George's high school team, Connie wanted his help to figure out who to bet so that she could win. The episode sneakily introduced someone who looked like a moneylender named Vincent, who followed Connie to Louisiana to remind her that he needed his money back. Although the scene was played off as funny as Connie eventually won at the slot machine she was using, offering the moneylender "a down payment in quarters," it still highlighted Connie's frequent gambling.
Learning that Medford's local illegal gambling secret room was shutting down in Young Sheldon season 5, episode 4 finally gave Connie the chance to capitalize on her life-long habit, buying it off and starting to actually benefit from it. As she explained to Dale, by gambling her whole life, she was always losing to the house, making this investment her "chance to be the house," finally winning more than losing because she wasn't gambling. While most characters close to Connie opposed her illegal business, including Pastor Jeff after discovering it in Young Sheldon season 6's ending, its existence finally transformed Connie's habit into a better story and something not harmful to her.
Young Sheldon developed story arcs sometimes over entire seasons, but it rarely had stories overlapping the whole series. George and Mary's marital problems were one storyline, established early in Young Sheldon season 1 that continued to various degrees in all six seasons. However, George and Mary's difficult marriage was already established by Young Sheldon's parent series The Big Bang Theory, making the story's existence necessary, as the prequel needed to explore it. However, Connie's gambling story was another thing entirely.
The references to Connie spending time in gambling rooms established Connie's gambling from the beginning of Young Sheldon season 1, making it one of the few stories besides Mary and George's marriage problems that have been developed throughout Young Sheldon's six seasons. This made Connie's investment in the laundromat the culmination of her gambling story, as it let Young Sheldon finally tell the story from another perspective, where Connie still faced various problems, but those weren't connected to her gambling, instead stemming from running an illegal business. This way, it also gave more importance to Meemaw's gambling den story in Young Sheldon by having it almost entirely disconnected from The Big Bang Theory.
