The funny thing about him hating Chapo Traphouse is that they have a younger, more politically involved audience. Sure they might be "Bernie Bros" but they actually go out and support/fund political figures. They are the actual future of the Democratic Party and not Hillary shills that just wail on the internet about how she should have won and that people should blindly support the next neoliberal candidate. Personally, I don't like Chapo Traphouse and their overly ironic humor, but I can see that they and their views are a more likely future in comparison to a Clinton neoliberal dynasty.
This is another thing that shows that Bob cannot let go of the past and assumes that the established "order" today will be, or at least should be, the "order" tomorrow. It causes him to constantly bet on the wrong horse. This is shown in his fanatical defense of his gaming journalism "friends" in an attempt to gain brownie points not realizing that gaming websites where on the decline and YouTube personalities and analysis where the future. I remember back when he worked for the Escapist he showed his arrogance once in an argument with someone on Twitter when they ask what was the difference between him and a YouTuber was and he responded, "I'm not wearing hockey pads" which is hilarious in hindsight.
TLDR: Despite going on and on about the superior future, Bob cannot move on from the past and adjust his vision to a possible realistic future.
