I also took Professor Winston's seminar in college and have similar feelings about it. It was far and away my favorite class and the wisdom in his advice has only become more apparent over time. At its heart, it was really about how to understand and communicate ideas.

One of the things I treasured the most was that Professor Winston overtly subscribed to the "make topics crystal clear and broadly accessible" school of technical communication. He would contrast this against the "make things incomprehensible so everyone thinks you're brilliant" school of thought. I am eternally grateful someone biased me early in life towards the former, not just when I'm speaking but when I'm choosing what to read and who to listen to.

I've also wondered lately what he would think about the current LLM wave. I'm sure he would have had a characteristically clear and profound take. I feel the world is losing out not having his voice during the current moment.