Maybe some other of his paintings will help us to answer this question.
Officer Of The Hussars
Judith beheading Holofernes
Portrait of Barrack Obama, see hi-res version here
Any idea so far? For sure no one will question the painter's talent which is as clear as his position towards Caucasian population. Mr. Obama obviously has no problem with that. It's good to know at least where he stands.
Mr. Obama said he picked Wiley because "he is different". Well, that's diplomatically said. Here he adds:
What I was always strucked by whenever I have seen his portraits is the degree to which they challenged conventional views of power and privilege.
-- Barrack Hussein Obama
And I can add that Wiley's paintings are often modifications of well known arts depicting some historical context modified to send some racial message which can be quite obvious from the paintings above, like black person in power position (it might be not the best expression for beheading) over "a bad" white person (even in case historical context or the original painting doesn't imply any racial context and that is quite alarming). To be correct I must to add that many (if not most) of Wiley's paintings are more or less neutral and don't express such an hostile stance but that doesn't explain why some definitely do.
Personally, I'm quite glad that Mr. Obama showed us some his colors and preferences.
And if you are shocked, don't worry - as @felix.herrmann mentioned - #itsokaytobewhite yet :)
Resources
There are more details uncovering even some really disgusting facts related to this topic not included in my article. Feel free to discover more: