The idea to write this book—as a way of paying tribute to a handful of very important individuals who have shaped my understanding of basketball and of life, and who have contributed to my ongoing search for what it truly means to have character—has been percolating in the back of my mind for years.

But it wasn't until the waning minutes before my appearance at the Democratic National Convention in Denver on Monday night, August 25, 2008, that I made the conscious decision to put pen to paper. Of course, writing a book was the last thing that I needed to be thinking about at that particular time for me and my family, not to mention in those very moments while standing backstage—where I was attempting to go through the equivalent of my pregame ritual that allows me, as a coach, to remove myself from the hubbub and become the calm within the storm for my players. But this night, for lack of a better description, was a whole other ball game!

Not that I was nervous about stepping out into the glare of history's spotlight. On the contrary, nothing could have been more gratifying than the opportunity to speak from my heart in introducing my sister, Michelle Robinson Obama, to the thousands of incredibly energized delegates at the Convention Center and to the millions of Americans watching. The weight of the moment, rather, had everything to do with the unbelievable responsibility that had fallen to Michelle. As the headliner of the convention's first night, my little sister, Miche, twenty months my junior, my only sibling, now wife of Senator Barack Obama—who was about to become the party's nominee for president of the United States of America—had to deliver the speech of her life. Intended not only to welcome the delegates and help reunite the party after what everyone agreed had been the most bruising primary season in modern times, the speech also had to deliver the most important character reference for the candidate that would be given throughout the general election season to come.

In basketball terms, at least in my thinking, Michelle was being asked to sink a three-pointer at the buzzer in a do-or die game at the start of the championship. Everything to come, victory or disappointment, would hinge on this one shot. And all I could do to help was simply pass her the ball. And believe.

As if reading my mind, just as I turned to follow a production assistant to the spot from which I would enter onto the stage for my speech, a glowingly confident Michelle popped her head out of the green room and hurried over for a last-minute hug.

"Craig," she said, with a look in her eyes that spoke volumes, letting me know that she was ready to cross the threshold into the public eye and to become, potentially, the most influential woman in the world, "thank you."

"Thank you." I grinned in response, thrilled to be along for the ride, as surreal as it all seemed. Both of us were probably thinking the same thing—how grateful we were to have our mother, Marian Robinson, on hand for this occasion and to take part in this most unlikely of journeys. And I was sure that on this night, of all times, Michelle and I both missed our dad, the late Fraser Robinson III, more than ever. Then again, I was just as sure that he was very much present, smiling down on us, reveling in the possibilities. "Mr. Robinson," one of the staffers whispered with a mix of politeness and urgency, pointing me toward the stage where I would enter in darkness during the last minutes of a video about our family. Before I turned to go, Michelle, playing coach for a minute, gave me a last once-over, nodding with approval at my choice of attire—a tailored black suit with an orange tie that my wife, Kelly, had picked out, with input from my son, Avery, and daughter, Leslie. Four months earlier, in the midst of the fever pitch of the presidential primary season, I had accepted the post as head coach of the men's basketball program at Oregon State University. We had only recently started to acclimate to Providence, Rhode Island, where I'd spent the last two seasons as head coach at Brown University, but the opportunity to move to a Pac-10 school (its subbasement record at the time notwithstanding) was too great to pass up. With the season set to start in days, I knew what a boost it would be to wear the school colors as a shout out to Oregon State.

"Well?" I said, with a final it's-now-or-never shrug to Miche, making sure that we were both good to go.

She answered by doing something either one of our parents might have done: She stepped forward to straighten my tie, a gesture of love and pride, no words necessary, and then turned to go toward the other side of the set from which she would be entering.

Now it was time to take my place on the stage in the darkness and wait for the lights to come up. Was this crazy or what? The question uppermost in my mind while I stood there in the dark was, How had all of this happened? It was one of those out-of-body experiences others had described before but that had been foreign to me until now—with floodgates opened and scenes of my life passing in front of my eyes, memories from the past coming at me from every direction. Everything was so vivid—all the stages of my own journey and those of loved ones, the critical turning points, the all important counsel sought by me and by others, and then the everyday, ordinary family upbringing in the Robinson household on the Southside of Chicago that was the primary music of my childhood and youth.

As if no time at all had passed, what suddenly came into my awareness were word-for-word conversations shared with Dad over the course of many years about the game of basketball—which to him was indeed a game of character. This wasn't our only topic of philosophical interest, but because basketball was a personal passion and serious pursuit for me, I was especially attuned to his analysis as to how you could tell everything you needed to know about someone by how they played the game—whether it was the dog-eat-dog combat of street basketball in the neighborhood, or the more structured play at the high school level, or at the top tiers of collegiate and professional basketball, or in a more casual game of pickup ball.

As someone who embodied character in its truest sense, Fraser Robinson spoke with authority. And without a doubt, I listened. Here was a man who never missed a day of work, sometimes doing double and swing shifts for the City of Chicago at the water filtration plant, and who would come home to spend time with the wife he adored and the two children he loved—as fully engaged in his role as husband and parent as he was at everything else in his life. It is noteworthy that I often have to remind myself that he did all this while he battled the debilitating disease of multiple sclerosis. Never once in any of my memories can I recall seeing him walk without a limp. Yet never once can I remember him complaining, even when he went from using one cane to two, and in those times when he needed help getting up and dressed in the morning and, later, more help just getting around. When Dad made observations about how players revealed different parts of their personalities on the court, the point wasn't for me to agree wholesale with every opinion. Instead, he was encouraging me to do what both he and Mom wanted their kids to remember throughout life—to think for ourselves and come to our own conclusions. This was obviously great training for the basketball player and future coach in me; learning to see the subtleties in the code of ethics that different individuals brought to their game—whatever game it happened to be—would have other valuable applications along the way. I learned to see how certain players could be horribly selfish—and, in spite of certain skills, were not guys you wanted on your team—or how others were phonies and would keep up a front, only to undermine the team when the going got tough. On the flip side, I learned to spot the characteristics of players who could play well and who could raise everybody else's game around them. I developed my own theory about the spectrum that ran from those who played merely to have fun all the way to the other side, where you would encounter players who had to win at any cost.

"Remember, Craig," Dad told me on one occasion when I was disappointed a teammate had let me down during a game," not everybody can do everything." That would be a recurring theme. Sometimes the guy with the most character couldn't shoot to save his life but was the ideal captain. Sometimes the star shooter who could hit the three-pointers from anywhere on the court was a ball hog and couldn't be relied upon to pass the ball when the pressure was on. This conversation also yielded the conclusion that it is usually as games wear on, when players are fatigued and have been in the trenches for a while, that their true colors really show.

Growing up, Michelle wasn't in on the details of these discussions. But given our proximity in small quarters and as a tight-knit family, through osmosis she must have just absorbed the notion Dad and I had embraced that you can tell a man's character through the game of basketball. Or at least that's what I suspected when she came to me with a very odd request several months after she had started dating one young man by the name of Barack Obama.

As I stood there in the darkness at the Denver Convention Center that momentous August night, thinking back to Michelle's request eighteen years earlier, circa 1990, I can honestly say that there was nothing about this very bright, handsome, poised new beau of my sister's that bespoke of some auspicious destiny. But let me quickly add that judging others based on what or who they might grow up to be was not the Marian and Fraser Robinson way. We were taught to recognize others for who they were, not for who they could become in the future or who their pedigree or résumé presented them as. At both college and graduate school—not to mention in earlier stints as a professional ballplayer and as an investment banker before changing course to pursue my true dream of being a coach—I'd met plenty of guys with impressive pedigrees and CVs whom I would have never considered worthy of my sister. So I wasn't looking for her to date someone who could become president of the United States of America or who would provide for her in material or impressive ways. I wasn't worried about that. Whatever she decided to do, Miche could provide for herself and forge her own future. What I wanted for Michelle was what our parents had and what I would later find in my second marriage, when I met Kelly—to be in a partnership with an ability to provide for each other, to build a home and family together. What mattered most of all was that they loved each other and had similar values and aspirations, could balance decisions with teamwork, develop the ability to compromise—and every attribute of marriage that makes a relationship a great relationship.
Granted, it wasn't easy to pass the approval test in the Robinson household—although I have to admit that the first time we met Barack, he couldn't have made a better impression. On a memorably hot Chicago summer evening, my parents and I were sitting out on the front porch when the two of them strolled up, stopping by to say hello on their way to a movie.

Out of earshot as they approached, Mom said, "Well, he's tall." With my sister being five-eleven, that was a good thing.

Dad nodded, adding, "Not a bad-looking guy either."

Michelle introduced him, no differently than she would have anyone else she dated, and he was very self-possessed, I thought—with a nice smile and a firm handshake. He asked questions and answered them with ease, as if he was used to jumping into new situations and genuinely liked people. I could relate. But it was when he talked about his family—even though his experiences were different from ours—that I saw a similarity in values that could definitely work to his advantage in their relationship. At the least, I concluded he was the kind of guy my sister wouldn't run over!

But no sooner had Michelle and Barack left for their date than Mom and Dad exchanged knowing glances and I let out a sigh.

"Too bad," Mom said.

"Yep," Dad and I said in unison. Then my father added, "She'll eat him alive."

Mom gave the relationship six months to last.

It was almost a year later—the point we were taking bets about when she was going to move on, as usual—when Miche came to ask for this favor that nearly floored me. From what she could tell, there was nothing not to like about Barack. But now she wanted to have some insight about what kind of guy he was when she wasn't around. And since Dad and I had preached the gospel of basketball being the true revealer of character, Michelle had come up with the idea that I include Barack in a game of pickup basketball and check him out.

Normally, I would have laughed at such a preposterous suggestion or complained bitterly about being put in the position of having to basically create an audition situation. But I was so happy that she really liked this guy that I agreed (albeit begrudgingly) to arrange a pickup game with a group of guys who played at mixed levels—mainly from their college days in the Ivy League and in Division I basketball, but also a couple who hadn't gone further than high school, and then a player or two who had played professionally. We all gathered a week later on a sunny Saturday spring morning at a neighborhood high school gym at the University of Chicago Lab School. It was here, in this beautiful old gymnasium—with the tall, thin windows I loved for their view of the trees and the graceful campus outside—that I had spent many hours in a volunteer coaching job back in those days when I was not yet ready to leave my career in the financial field. Our pickup games often took place here, so there was nothing forced or unusual about the vibe as everyone arrived, on time, ready to play. Barack strolled in without any apparent intimidation, thankfully unaware that he was being vetted. Nor did he seem to detect anything out of the ordinary when I made sure that he was on my team—so I could keep an eye on him—as we began a series of five-on-five games intended to take us all through the paces for the next hour and a half.

My initial concern was that Barack would be so far out of his element that I'd have to protect him on the court—not wanting him in any way to lose face. The other worry was that he might turn out to be one of those jerks who is oblivious to everyone else on the floor but himself. Almost as soon as we started playing, it was clear that I didn't have to worry about his competence. He was a typical basketball player who could hold his own, though there was more to be determined in terms of skill and character. The first test, however, had been passed.

Then, as we played on, came the next set of clues that he had definitely attained experience in the game at some point—which turned out to be high school basketball. And, lo and behold, Barack Obama proved to have some skills. He had a nice little shot and liked to go to the basket. He played with guts. Interesting. He also knew how to find the open shot. Excellent. Definitely a very left-handed player—not like some lefties who have developed right-handed maneuvers and can even outdo other righties. But Barack used his strengths to compensate for his weaknesses. Self-awareness! The more we played, the more he showed his basketball intelligence—the fact that he had knowledge of the game. He didn't have to constantly score to show he could play. He knew when to pass and when not to pass (even if he preferred going for that open shot). He knew when to cut, when to set a pick, and what to do after the pick. In my terminology, he knew the x's and o's, the nuts and bolts, of basketball.

Better still, Barack conformed to the unspoken rules of integrity that apply in these friendly but highly competitive gatherings where there are no refs. That meant when he fouled somebody else and was called for it, he didn't argue, but gave it up, acknowledging the push or the trip he'd committed with a mea culpa nod or by saying in a very cool, matter-of-fact way, "My bad"—and then allowing play to continue. When he was fouled, depending on the degree, he called it without overdoing the dramatic indignation or flopping that are usually signs of bad habits.

It should be mentioned that compared to most of us out there that day—me at six feet six plus, then at a medium build, and guys like the muscular Arne Duncan at six-five, who had been co captain of his team at Harvard (later to become secretary of education for the Obama administration)—Barack was definitely on the slight side. Now, not everyone in our group was a big guy. My longtime friend and colleague John Rogers—who was captain of the team at Princeton when I arrived to play there and who opened doors when I entered the business world—was only six feet tall, more than an inch shorter than Barack. Then again, Rogers packed so much power into how he moved and shot the ball that he would later famously beat Michael Jordan in a game of one-on-one. So, looking at Obama as he was then, you might have come to the conclusion that he'd be hitting the hardwood most of the time. Not so. Of course, I knew that in basketball—as in life—you never want to infer too much from appearances. That said, I gave him brownie points for toughness. What was revealing as we reached the midway point—with each team having lost some and won some—was that Barack had come to play and that he knew the object was to keep playing. For that, I was willing to conclude he had passed the test with flying colors. But two other character traits didn't go unnoticed. One of these showed up after over an hour of playing and some of the guys were starting to tire. Not Barack. He seemed to have a quality that I've seen in leaders throughout my life—a capacity for what I call being relentless, for drawing from some inner wellspring of energy when others are running out of gas. And the clincher, even though he had no clue he was on an audition, was the fact that he was dating my sister, and he could have done any number of things to try to impress or kiss up to me, and he didn't! If he was a phony, by the time he started to fatigue toward the end, he would have done or said something embarrassing to either try to boost my ego or assume a level of closeness that wasn't there yet or showboat in some way. None of that happened. We were three-quarters of the way through the session when I gave in to major relief. Phew! I could report back to my sister that he was a normal player, someone who could continue on in our regular game, no problem. He was real, down to-earth, a good guy.

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. "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. Much back-and-forth followed and eventually, as evidenced by where we had gathered in August of 2008, impossible though it had once seemed, the effort paid off. Even so, as the final seconds ticked by before the lights came back up in the convention center, with the tidal wave of memories gone and my senses focusing back on the present, I still had to laugh that even with my sister and brother-in-law both being Harvard-trained lawyers, the basketball coach was called in to help negotiate the deal!

Let me hasten to add, however, that it was the courageous actions taken by our current First Family and by every single person involved in the historic campaign that led to its final outcome. Which leads me to a fundamental teaching my parents always emphasized—that life happens to you, putting choices in your path that offer an abundance of opportunities as well as challenges (and sometimes both), and that the best choices are usually the ones that require courage. They may demand that you raise your level of play beyond anything you ever knew you were capable of, but those are the choices most worth taking.

And really, that's what most inspired me to write A Game of Character—not only to share with you what I've learned(and hopefully passed on to my children and to my players),but also to help reclaim the value of character that I believe is as intrinsic to basketball as it is to life. What's more, as the pages ahead will elaborate, true character is a quality that can be found everywhere and anywhere, in some of the least likely places—including the Southside of Chicago, which is exactly where we're headed next.