@NameLlama,
Yes, Rob has encountered loathsome people. They're people I'd repudiate in the strongest terms right away. And it is maddening to see that Rob doesn't.
Why not? In part, because Rob never stops seeing himself as a christian evangelist who can "save" such people. To him, they're not "loathsome" because no human being is beyond redemption. And he tries – very awkwardly, I must say – to engage with them.
I'm chagrinned to see him or anyone step over such racist views without challenging them directly. But if you imagine a priest or missionary trying to develop a rapport with a bigot, then you might understand why they'd try to soften the differences of opinion (like racism) and emphasize common ground (like distrust of the media and censorship) in order to ultimately persuade the person to give up the incorrect view. Genuinely, Rob always sees himself in that role of missionary.
To me, this approach seems naïve. I don't believe these bigots show any signs of moderating their views, whereas Rob chooses to highlight the "good" in such people. The lack of direct condemnation of their bigotry makes Rob look like an accomplice. Rob's breezy optimism and tendency to "reach out" to the worst people make for disastrous PR.
I don't approve of Rob's approach. In my opinion, he should condemn bigotry right away and not sidle up to it with mild complimentary expressions. What could be worse than that? But I know from private conversations that Rob doesn't share those bigoted views. He genuinely believes he is going to convert the bigots toward tolerance.
As I mentioned earlier, this has me pulling my hair out. Very few people are going to understand or be sympathetic to Rob's extremely charitable attitude toward bigots. Yet I can understand that it is – partly at least – an extremely christian attitude toward sinners.
What further muddies the waters is that Rob's own political views are conservative and somewhere on the "right". That means he does have some common ground with people who are much more extreme than he would ever be. He is not alone in minimizing the problem of white supremacy. Fox News and other right-wing media outlets have done so for many years. Congressman Steve King has expressed openly white supremacist views ad nauseam, yet a majority of people have re-elected him year after year.
As a progressive, I'm never going to be satisfied with the genuine opinions of people in much of the USA. They elect bigots like Steve King and Donald Trump to government and cheer them on because they share some of those attitudes. Those views will be around until those people kick the bucket, if not beyond. Some of the people who vote that way and think that way are going to be CEOs. Rob is far from being alone.
I don't know much about Rob's politics because, as an employee, I don't try to bring up divisive issues with my coworkers. Though Rob has some right-wing views that seem absurd and wrong to me (as a progressive), Rob is not a bad guy. I have seen the way he interacts with muslims and others. He's not only tolerant; he's welcoming.
Rob has crossed a line. And he will have to come to terms with the PR consequences, if nothing more. We should not excuse bigotry of the kind Rob has sidestepped in public. Based on private conversations, I know that Rob doesn't excuse or share it. He too should denounce it.