If you think about it must have come as a surprise when he turned on the tv and saw Tom Brady still winning championships 16 years later, considering that he supposedly is an NFL fan some dialogue would've been nice. I would do whatever it takes to get reinstated in prision in his place.
Also, it's not really worth complaining the obvious recemblance to the other VN, it was wrote with the same dialoges and everything, made that way deliberatly. I don't think it is be the best path to take but well... decisions, decisions