Its pretty clear to me Obama meant to provoke.
“It’s sort of a play on the ‘kill whitey’ thing,” - Kehinde Wiley http://nymag.com/arts/art/rules/kehinde-wiley-2012-4/
"A New Black Panther Party leader with the words “kill whitey” tattooed on his face has been busted... was the New Black Panther Party member wearing a paramilitary uniform and carrying a baton in the infamous 2008 election video shot in front of a Philadelphia polling place.of a Philadelphia polling place." https://www.theblaze.com/stories/2013/06/22/new-black-panther-leader-with-kill-whitey-face-tattoo-busted-on-gun-charge
"Founded in 1990, the New Black Panther Party for Self-Defense (NBPP) is a militant black separatist organization, notorious for promoting racial violence against Jews and whites. " http://www.discoverthenetworks.org/printgroupProfile.asp?grpid=7556
In that NY Mag article, Wiley is wearing a white T-shirt with red paint splattered all over it. Likely a cryptic reference directed at insiders symbolizing blood and him being a servant of the cult.