Du-rag isn’t inherently derogatory. As many have noted, it’s a very common thing worn by African-American men. It’s the way that Brenly felt compelled to point out an old great like Tom Seaver wouldn’t have ever worn one that made the comment racist. It was a pointed comment on how the game has changed, and implied not for the better. Fwiw, I don’t think it was meant to be racist. But it was insensitive. So the sensitivity training feels appropriate here. Yeah, I think Bob was just making a joke, but it wasn't a good one, and considering the source it felt worse than it might have coming from someone without this kind of history.