Yeah what he is doing is he plays with Old Master painting prototypes, most of those are biblical or classical allegorical, when secular art was rare.He uses ordinary people from his own hood/tribe/background and puts them in the place of ancient biblical or allegorical or royal figures of past art.

I think the intended effect is to make the viewer compare present and past. You can read as much racial message into that as is your wont about race in the present era. I don't think he is intending to force racial animosity down people's throat, though, he is more messaging: this is what is now. It is more Warholian: the ordinary are now our kings and queens.

from Warhol’s 1975 book, The Philosophy of Andy Warhol.

What’s great about this country is that America started the tradition where the richest consumers buy essentially the same things as the poorest. You can be watching TV and see Coca-Cola, and you know that the President drinks Coke, Liz Taylor drinks Coke, and just think, you can drink Coke, too. A Coke is a Coke and no amount of money can get you a better Coke than the one the bum on the corner is drinking. All the Cokes are the same and all the Cokes are good. Liz Taylor knows it, the President knows it, the bum knows it, and you know it.

Edit to add: the biblical story of Judith and Holifernes was one of the most popular themes of Old Master Baroque painters, precisely because it was so dramatic, bloody and allegorical. It's like:everyone did that one from Rembrandt to Rubens to Caravaggio, be there or be square, one of their greatest hits.

So as to be clear that I am not making his popularity up, and it is not at all exclusively Afro-American and it very much includes "flyover country" and the entire world. Here is a review from when the retrospective show was at Fort Worth Museum. He is so popular that his work might be considered declasse now among the real hoity toity art cognoscenti, precisely because it is not controversial and therefore panders to people who want something contemporary but not "difficult." The beautiful realist style is not difficult to like. He pays a lot of attention to current fashion and style. He is at  such a high sales he has a large studio of assistants who help paint the intricate backgrounds. It is not meant to be "in your face" politically charged. He is about as controversial as Beyonce or a major black fashion designer. All of which, I suspect, Barack Obama totally understands and is why found his work simpatico, it is: moderate.

With my underlining of a line that expresses his approach as to Old Master biblical themes:

Exhibit review: Kehinde Wiley’s spectacular mid-career retrospective at the Modern

By Gale Robinson @ Fort Worth Star Telegram, Sept. 23, 2015

[....] All the women have a similar look, though, and one that is more challenging than the men’s. They look fierce.

Wiley is very attuned to the fashion dateline and he seeks out models who seem equally aware. He marvels that the sell-by date on fashion expires so quickly, citing the velour tracksuits by Sean John he painted in 2006 that look so dated today.

In-demand artist

This exhibition includes sculptural portrait busts along with pieces he calls stained-glass paintings. The latter are not paintings at all. Instead, they are traditional stained glass, made by stained-glass workshops in central Europe that have been making them for generations. These glass window portraits are in a black chapellike gallery, and his black and brown men are depicted as saints, heroes and martyrs.

“Society portraits don’t give you the oomph that religious ones do,” Wiley muses.

The glass portraits glow, as is the nature of stained glass, but they are not as luminescent as his painted men.

With all of his new mediums and world travels, Wiley is stretching himself thin. His popularity has created an enormous demand for his work, both from institutions and the very wealthy who want commissioned portraits. His travels have exposed him to more demand, and he tries to give back by opening studios in the poorest countries.

Wiley has a huge phalanx of assistants who paint his labor-intensive backgrounds. Lately, however, it looks as if he is expecting them to paint the bodies, too, and the results are obvious in one of the very last paintings, one that features two young girls. Their arms look like those of mannequins — plastic and unyielding

The assistants can’t imitate his touch. His inimitable style has created a problem. Even with assistants, he cannot keep up with the demand [....]

To give such Trump fans comments serious attention is just feeding the artificial dragging back to 1980's culture wars which themselves hoped to return to the 1950's.  Our culture, even our pop culture, which Wiley had been edging into and now is firmly ensconced in, is far more complex than that now. There's no going back to the America they are fantasizing about. Including on race, most of us are way beyond that, we imbibe Afro-American culture as part of America now every day. So does the rest of the world, for that matter.

P.S. Michelle's portrait is actually more radical, art-wise.