Dude is insanely talented and he is intelligent. His weakness is ego and a tendency to condescend. As popular as he is on the left, his biggest fan is Barrack Obama. The best mansplainer in history.
I agree. Given traditional voting history any African American who is considering Trump is probably naturally a contrarian who will dare to question the status quo.
The last thing you want to do to win over a contrarian is explain to them in a condescending way that they are wrong. Especially when the basis for your argument is style / race. Not policy.