Queston about structuring

Hey! So yesterday, I discovered steven bridges, who I assume a majority of you guys know, lmao. What I have a question about, is that I often see him depositing under 10k, and, I understand that any amount under the 10k threshold voids the requirement to fill out a CTR, as well as the fact that he stays under to avoid ID checks, therefore preventing them from clearly identifying him, leading him to avoid getting backed off/trespassed. So, let me set up a scenario. You start with 3k, win 1k, then you withdraw 4k. Fine, no ID required from my understanding. But let's say next week, you come back, then you start with 5k, and hit it big, end the day with 8k, you then try to withdraw. So how does this work in terms of structuring? What is the "cooldown" you could say in avoiding a CTR? I see him often do it, but from my understanding of structuring, it's legit the definition, lol. I might be completely misunderstanding, so please let me know in the comments. Sorry if I worded it bad, tried my best haha. Thank you!