Cantrill is really an interesting character who has been through some hard knocks (Sun -> Oracle) and what must be some very stinging disappointments over the course of his career. I think it's a reasonable inference that at some point, a smart, high-level engineer like himself would have wised up to the game. Right now, that's the best interpretation I have for his conduct re: pronouns, and some of the more transparent sales pitches that bleed through his presentations.
His talks are really intriguing for me personally, as I find it therapeutic to try to watch him narrate his conflicted feelings on the rising containerization revolution; I hold many of the same views, including a deep disappointment for the way this has all played out; I can only imagine it's worse for Cantrill, who, as an Solaris/OpenSolaris/illumos dev, has been dealing with this type of disappointment for 20+ years.
In one talk, he compares the complexity of a modern devops infrastructure to a nuclear reactor, and in another, he talks about it in terms of God granting fire to mankind, before mankind puts it out without learning to cook because they were afraid that it was too hot. He talks about how he is going to try to discuss some containerization fads "without having an aneurysm".
Cantrill is great and we need more visibility from people like him.