His open condemnation of the word "Islamophobia" in response to a non-binding motion and posing with a guy wearing a "I'm a Proud Islamophobe" t-shirt inbetween the somebody shooting up a Canadian Mosque and the Christchurch shootings to me is a sign he was getting too mired down in politics and missing the forest for the trees. In both cases there was evidence the shooters were wrapped up in "Intellectual dark web", alt-lite, and alt-right circles and it seems like he missed the danger that others saw because he was blinded by the perception of progressive overreach.

He also has a bit of a reputation for twitter toxicity and he later ended up with anxiety issues and consequently an addiction. It's hard for me to not see him as a cautionary tale of why to avoid getting wrapped up in politics and the culture wars.