Again, Michelle and Barack were only dating at the time. It wasn't as if they were engaged or, worse, that this was happening at the bachelor's party. Or at least that was in my thoughts when I began to appreciate the method to the madness and went to give my sister a glowing report. Summing it all up, I gave her the verdict: "He's very confident without being cocky." He had passed the test with a definitive thumbs-up on his playing and his character.
To what extent this input helped give Barack the edge a short time later when he proposed to Michelle and she accepted, I can't say. But the bottom line was that she said yes!
As much as I might have grumbled at the time, in hindsight, I could only feel honored that my sister trusted my assessment enough to ask for it. And that was the same sense of honor I felt some sixteen years later, in late 2006, when Barack came to me for advice and direction on an issue of great importance to him—a possible run for the White House.
"You mean—right now, for the '08 election?" was my immediate reaction when, without any prelude, he brought the subject up after I'd stopped by the Chicago Obama household to pick up Avery and Leslie, who were visiting with their cousins and spending time with their grandmother.
By this stage of the game, Barack was two years into his role as the junior senator from Illinois in the United States Senate, and I was just starting as head coach at Brown. My brother-in-law and I were used to conversations on the fly about our eventful lives—in this case literally on the fl y, since I'd just fl own into town. Barack and I had gravitated, as usual, to the kitchen, the hearth of the home, for something to eat and to get caught up on the concerns of the day. Of course, it hadn't been inconceivable that someday in the future he might be a candidate. But this was sudden.
Barack answered me by saying that, yes, he was referring to '08 and that there was meaningful interest in him as a candidate. Advisors who had worked on his Senate race, along with new partners, were telling him that this might be the right time to mount a bold, different kind of campaign built on grass roots and the nation's growing desire for change.