I took a Distributed Systems class with Prof. Cheriton in 2007 for my Masters degree. In the first few classes, I remember being awed by the wealth and legacy of the man, and wanting to glean everything I could from him. It quickly became apparent though that he hadn't updated his course materials or lectures in over a decade, e.g. the pros and cons of distributed shared memory vs COBOL RPC. The core topics were there, it was just presented in such a dry manner.
Worse though, was that he would needlessly inject his very conservative politics as total non-sequiturs. Test questions like "Hillary Clinton wants to build [obviously unscalable system], explain why it won't work. I found it very unprofessional.
Stanford records a video of every lecture, and enrolled students can then watch them whenever. I remember sitting in my dorm room, watching one of his 75 minute lectures where there was literally 3 students in a 150 person auditorium. It just floored me that this was how a billionaire was spending his time. I do genuinely like the man, you could just tell he was capable of so much more.