Maybe in private he wouldn't. But if you think he (or any other white person in this country) would feel as comfortable talking about black problems in a public arena as they do taking shots at (mostly poor) white people you don't have a very good read on today's political climate. Talking honestly about race issues would be career suicide for pretty much any high profile white person. Pretty much all any high profile white person could get away with talking about race is criticizing "white privilege," which is why most high profile white people won't comment at all on race politics. Which is why I found his position that we need to address uncomfortable topics which all the SJW types on ESPN and social media are lapping up very ironic and hypocritical.
Also, I don't know much about Pop's politics. I know he is really into war history. I actually would have assumed he was more conservative because of this, because white guys really into war history tend to skew more right wing and if you did deep enough you can normally find some Confederate civil war and Nazi war stuff in their closet (pun intended).