Before Jason was a played character I think it was intended to be a fuckup.

But having played Jason, I think it's totally something he would do. He loves to take a gamble.

Please do note that he was likely not trying to take out major DEs because they were "bad buys," but because it would provide him with something beneficial, one way another. Jason is a good-natured opportunist, and little past events like these helped me to shape his character from NPC to PC.