I personally find Bob enjoyable to talk with and hold his New York speech patterns and tendencies as simply as part of the culture he is a part of, being familiar to me and comfortable due to my New England roots from long ago. We had conversations before the conversation you saw about what we would talk about, and I think were both happy with how it all went.
As to Trump, the conversation regarding him actually served me well as a vehicle to talk about the general subject of narcissism and the Cluster B personality disorders in general, particularly in the at least somewhat awakened, as a substantial portion of the trouble in the DhO itself, its sister communities, and most Buddhist communities in general has resulted largely from the presence of those traits among practitioners, many of which are poorly addressed or even entirely unaddressed by fundamental insights, or though to have been overcome and eliminated by practice entirely when they hadn't seemed to have been so in practice, and thus it had relevance for me related to recent life events of some consequence, so I found talking about the topic, even in general terms, somewhat cathartic, as well as rarely discussed and thus relevant, as well as a good set up for some of what appears in MCTB2.
Daniel