I think some people are misinterpreting the skit.
Basically, the message was, the cynical, knowing black guys have been around the block (i.e., around the country) more than the naive, clueless white liberals and know that the country is largely racist, contrary to the idealistic white liberals. The black guys laugh at the white women because the women say they can’t get ahead in Trump’s America, where the ‘truth’ of the skit is that black guys are the ones really oppressed.
Then, with typical liberal cognitive dissonance, Chris Rock suggests the liberals would have won if they had nominated someone like Obama (40 year old charismatic black guy) instead of an old white lady, which of course is inconsistent with the cynical black guys mocking and laughing about the white liberals’ naivete that the country is not racist.
The skit was mocking clueless white liberals for being naive about America while calling America racist.