I haven't experienced a true worst gambling moment so far because I have a lot of self control and I know that no one got rich with gambling so I don't have high expectations from it and this is the reason I have not yet suffered a worst moment in gambling.
It all depends from where you want to go with it and what do you want to achieve with this.
Wow, I envy you a lot, just because you haven't had the worst gambling moment, like any of it. I think you could share a couple of significant losses in a way and maybe share something that you know to prevent further losses. It seems that you are a pro in it. I had many sad moments in gambling, and it all involves losing, I think that's just the category that it is in. All in all, you won't feel bad if you know that you have managed your funds correctly.
It is clear that he has good self-control, once a gambler has what like he have then there will be no worst moment in gambling ever. Worst moment in gambling comes when you are so greedy, both while you are on losing state or winning state as most of the time you will just lose all what you have won as well as when you are trying to recover. I don't think he is a pro gambler, but he is a good gambler who knows how to gamble wisely.