John Cleese MSNBC just gave a precise explanation of Trump's thinking:

[Tanuki]

7. When Michelle Obama first started dating our future President, she asked

her basketball star brother Craig Robinson to shoot some hoops with him;
https://en.m.wikipedia.org/wiki/Craig_Robinson_(basketball)

"When Robinson's sister, Michelle, began dating her law firm colleague, Barack Obama, who played basketball recreationally, she asked her brother to play with Obama and give her a character assessment so that she would know whether she could become serious with him.[10][11] He gave an encouraging report to her.[9][12] As he later related, "When I played basketball with Barack, he was quietly confident, which means he had good self-esteem without being cocky. He was certainly a team player – he wasn't a pig, he passed when he was supposed to pass, and he cut when he was supposed to cut. To me, that speaks to a lack of selfishness. He had natural leadership ability, because he didn't just pass me the ball because he was dating my sister. Whenever a player gets tired, he reverts to the player he truly is. That's how you tell. And we played for hours. That's how I could tell."[10] The story of this pick-up game and of a "test" being passed became a key part of the Obama narrative.[10]"