Yup. It's like Tim can't figure out that him rolling around in the mud with a retard isn't going to score him a win, because at best he beat up a retard and at worst the retard rapes him.
Jack used to appear weekly, then he went traveling to have public brunches that anyone could buy tickets for with his super secret order of mega CEOs and millionaires. After coming back he appeared every other week, but it does seem like Tim is digging deep and having on more people who work for him like Shane Cashman.