"There is a window of opportunity," Barack said thoughtfully, letting me know that while he certainly hadn't signed on yet, he was seriously looking at the pros and cons. Then he surprised me by asking, "What do you think?"
All I could think at that moment was what came out of my mouth—"Wow!" He had brought it up so matter-of-factly, without fanfare or drum roll, that I was caught off guard. But as I found my bearings, I went further, telling him, "I think it's fantastic!"
My only frame of reference, yet again, was from basketball. To me this was along the lines of being considered the Most Valuable Player ever of the NBA championships. There had to be a better analogy I could offer. Since my present career had begun with an assistant coaching position at Northwestern and I had only recently advanced to head coach at Brown—with the intended turnaround just getting under way then, for me the coaching version of being considered for president would have to be this: to be appointed head coach of the winningest men's college basketball team in the country, the University of Kentucky Wildcats.
That was why, as we discussed the reasons that Barack might not be ready for a presidential run, I had to argue, "You know what? I may not be ready for the Kentucky job, but if somebody offers it to me, I'm taking it!"
After all, as we both knew, when windows of opportunity open, you can't count on them staying that way. At the same time, given the landscape at this point, even a political outsider like me knew that the field of candidates was already crowded. But long shot though it was, my feeling was why not? Between asking what the next steps were and how I could help, I had to add, "You're right, this is a window of opportunity to do good on behalf of a whole lot of people who really need it."
Barack seemed to take these words to heart and smiled as though encouraged. But then, less certainly, he added, "There's no way I can do this without having your sister and mother onboard." He indicated that Mom wasn't as adamant as Michelle—who was none too happy about the prospect of having to go through an ordeal that would be exponentially more grueling for her and the girls than the Senate race had already been. Barack then put it to me directly when he asked, "Would you mind talking to your sister?"
"Well, no, but if you can't convince her, I don't see how I can."
"You don't have to convince her. But let her know how you feel. She trusts you."
With that, I took on the herculean assignment of assisting Barack by approaching two of the strongest women in the world—Michelle Robinson Obama and Marian Robinson—and employing arguments and lessons that they both had helped teach me over the years.