While we still do not have a definite answer as to how long he has been upset with the company, we do know now that CM Punk was already contemplating a departure from WWE as early as Royal Rumble 2014. He vented to Mick Foley at the time about not being happy within the company and having trouble dealing with injuries.
One of the individuals that WWE was most impressed with during the Old School Raw episode was Scotty 2 Hotty. He stayed in really good physical condition and was still able to work a very solid match. Scotty even nailed his trademark Worm move well.