It seems to me that Jack got carried away with giving Chris money, because it looked like he did multiple smaller transactions that led up to the $1200 total. Correct me if I'm wrong. His story about having one last adventure before studies sounds like some desperation. His parents might be on his case to get his life going in a better direction, so he sort of retaliated by going full bore into an old interest of his, that being fucking with Chris Chan. Notice the trend of people interacting with Chris, feeling guilty about it and then giving Chris money? The difference with Jack Z is that he wants to have a big last hurrah where he really makes a mark in Christory before going to school again. Perhaps Jack is hoping that this will work out so well that he can be like Chris, he'll have such a following that maybe he too can sperg on the internet for play money like Chris does. Jack would rather be a celebrity lolcow than have the normal life his parents want for him.