Another angle to consider: wearing blackface in this context might not be as immediately offensive as its earlier uses. However, it’s still highly insensitive in the fact that a lot of people who don blackface give no consideration to the real life problems that black people face. This man has no problem dressing up as a black man to give a more “authentic” experience, but at the end of the day, he can take his makeup off and live with the privilege of being a white man. Given his dismissive response to Colin Kaepernick, I highly doubt this guy is giving back to black communities in any way, but he doesn’t mind taking their culture and image to make a profit. That's a problem.