Don't think he would be as confident if he didn't have the upper hand. Most times this dude is steps ahead of everybody else it's insane.
When Jay was scouted from the US by the president of Dream Entertainment, he already knew quite a bit about Dream and the problems it was facing. Mostly, that there was a threat of it being ruined by rich assholes that were interested only in making money and not by putting out a quality product. Chairman Kim was already on Jay's radar when he came on board, so Jay specifically targeted him and knew what moves the moldy fossil was going to make to try to takeover the company. So yes, Jay is confident because that perverted prune has been acting predictably. He's surprised Jay a few times by making a couple of expected moves, but nothing that Jay can't recover from
same face syndrome LMAOOO