“The Boss Wants to Play Pickup”

  Leadership & Management
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Jun 302014

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Chris, formerly trained as a NCAA swing-man guard-forward, was suddenly playing in the game of his life.

White House Photo. President Obama positions himself under the basket during a pickup game with Congressional members and Cabinet Secretaries at the White House Basketball Court.

One summer day back in 2010, a tall, lean athlete, Chris (anonymously named herein for United States Secret Service and presidential discretion), stuffed a pair of size 14 basketball shoes and a change of clothing into his gym bag. Instead of heading for hoops as usual at my Georgetown neighborhood gym, this athlete was instead escorted to Camp David by the United States Secret Service.

“President Obama wanted to play some pickup games before taking a vacation,” says Chris, who was frequenting my Georgetown gym, where a White House correspondent point-man for The President played as well. That’s how the invite came his way.

After playing a couple of pickup games with the White House point-man, “I got this text from him simply saying, ‘The Boss Wants to Play Pickup.’ ”

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White House Photo: President Obama playing pickup basketball at Camp David.

“Needless to say, I was kind of in disbelief, but I took him seriously, and I couldn’t pass up the opportunity, and so the rest is well history,” Chris told me just as causal, quiet, and humble as he is.

“The secret service was on guard, but they were very relaxed, because they knew The President had some pickup ball to play,” Chris says.

And boy did Chris bring it for ‘The Boss‘.

Skillfully trained in the game of basketball, Chris says shooting hoops with President Obama ranks near the top of his NCAA college basketball career memories.

But, playing pickup with The Boss is the highest-tier.

And, Obama plays a ‘mean‘ pickup game too recalls Chris to me.

“The President can play, Chris exclaims confidently, “he threw his body up into the ball a lot, and was really being physical with us in play,” says Chris with a nodding smile.

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White House Photo Credit: President Obama takes a shot during a pickup game with Congressional members and Cabinet Secretaries at the White House Basketball Court.

Chris recalls further how he just fell into ‘the zone‘ in play with The President, as just one of the guys, much like he did, while playing on the NCAA varsity basketball floor.

“I even had to block him once,” remembers Chris with some pride.

You would be proud too, if you had the chance to block The President’s stuff, like Chris did.

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“The President’s got a crossover and he’s got some fundamentally sound basketball moves,” as Chris breaks it down, “The President uses his body positioning well, and he out-smarts his defenders, when he gets the chance. He’s even got a ‘mean‘ pump fake, hopping under the defender’s arm, and at times, driving hard straight to the hoop” Chris analyzes.

“The President regularly posted up two points, recalls Chris, “assisting his side of 5-on-5 teammates on their way to victory in the game.”

Sounds like just a normal day at the office for The President.

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Photo Credit: Obama for America Campaign 2008, Former Illinois Senator Obama takes the ball to the hole as Reggie Love, green jersey, former Duke basketball team Captain, left, and Chris Duhon, former Duke basketball standout, right, guard the Senator in quick pursuit.

In fact, a bond between The President, and his young 29-year old and outgoing former personal aid, Reggie Love, now enrolled at The Wharton School, it is generally-known has been set on a basketball court. The pair played pickup games regularly during the presidential campaign, a practice that has carried over to the South Lawn of the White House. Love, a star wide receiver on the football team and captain of the basketball team at Duke, rarely plays against The President.

“Reggie is 20 years younger than me,” Obama said during his first presidential campaign. “So there is no doubt that I have to have Reggie on my team. I can’t be guarding Reggie.”

“I know definitely I’m going to miss that,” Love said. “He’s been like a big brother to me, a mentor. I’ve learned so much about life from him. I’ve spent most of my adult life working for him, so it’s going to be a challenge….”


Frankly speaking, I could never do what Chris or Reggie has done with The President. I am as tall as Chris at 6 foot and 4 inches. Many times, as I board a very tight commuter airplane completely bent over, folks on-board always ask me, if I ever played basketball.

Thankfully, Not!

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Watching me play on a basketball court is like watching Will Ferrell – ‘all-out laughs’ in some of his most classic physical comedy, if you can just imagine me on a basketball court.

In shooting the ball, my buddies repeatedly ask me, “How do you completely miss the entire back-board in sailing the basketball over it, when you take a shot.” I never make two points. We do not even think about me making any three’s, because it is hysterically funny to watch. I am such a ‘Gomer’ on the basketball court.

And watching me jump is just hilarious, especially as tall as I am at 6 foot and 4 inches, like Chris.

Dunking the ball is simply out-of-the-question hysterical. As jumping for me, looks like I have an old broken rusted-out ‘slinky toy’ attached to my heels and nailed to the floor. I jump up to nowhere near any kind of respectable heights. I usually come right back down fast with absolutely no kind of so-called ‘hang time.’ Sometimes, I even land face-first – learning quite fast that we have gravity here on earth. And, I should stay on it.

Usually my buddies are saying, “Stop! Please stop, don’t do that, stop! Our sides are splitting we’re crying laughing so hard.”

It is great comedic stuff watching me playing some pickup basketball. Let’s just say I won’t be getting a text like Chris did saying, ‘The Boss Wants to Play Pickup‘ anytime soon.

Notwithstanding, I love to watch Kobe, LeBron, and the NBA professional’s magic in the The Finals. Besides this, I love the college pageantry of March Madness, like The President and all of America in the spring.

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I personally believe basketball players are the most finely-tuned, cross-fit endurance, and physically-trained athletes. A basketball player’s strengths include a quick first-step, a long wing-span, an exceptional leaping ability, some miraculous passing like Magic, and a versatile 3-point range like MJ. Some swing-man guard-forward pickup players, like Chris and President Obama, are smart and accomplished in making sound floor judgment and providing unbeatable floor leadership.

You see it is all about the mind and the body coming together, as one team spirit and trust in each other, oftentimes in deep trusting bonds for life. I have experienced this, indeed, I am blessed to now say.

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Photo Credit: Andrew D. Bernstein/NBAE/Getty Images. President Barack Obama accepts a jersey and basketball from Lakers captains Derek Fisher (left) and Kobe Bryant (center) during a ceremony to honor the 2008-09 NBA champions.

A father’s legacy of pickup basketball.

It has been many times said, “The Road to the White House is through Cincinnati.”

My admiration of the pickup game is for good reason. In my family it has been all around me for a couple of decades.

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My stepfather is the great George Wilson, a two-time NCAA Basketball Champion and Olympic Gold Medalist. Currently living in Cincinnati with his lovely wife of 25 years – Jean Wilson, my mother – George was a member of the 1961-1962 University of Cincinnati Bearcats NCAA Basketball Championship Teams and a member of the Gold Medal winning 1964 United States of America Basketball Team – including former New Jersey Senator and 2001 presidential candidate Bill Bradley of Princeton – at the 1964 Olympics held in Tokyo, Japan.

As a 6’8” pivot man, George established ‘a mean hook-shot’ very early back in 1958, modeled after then-Northwestern great Joe Ruklick – way before the rise of Kareem’s famed ‘sky-hook’ a decade later at UCLA.

In 1958 George, a high school All-American (1956-60), led Chicago’s west side Marshall High School to a 31-0 record and the Illinois State Championship. In 1960 he was the inaugural winner of the Chicago Sun-Times Player of the Year award. George was also named All-State of Illinois in high school basketball for three years.

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Photo Credit: Longtime friends, Oscar Robertson and Jean Wilson, my mother, at a book signing of “The Big O” by Oscar Robertson.

Upon the urging of 1960 Olympic Gold Medalist in Basketball, the incomparable Oscar Robertson, who had just led the University of Cincinnati Bearcats in a buzzer-finishing heartbreaking defeat to Fred Taylor’s Ohio State Buckeyes – including sophomore basketball greats John Havilcek, Jerry Lucas, and senior Bobby Knight – in the 1960 NCAA Championship game, George later led the Bearcats back to a NCAA Championship in 1961 against that same Fred Taylor Ohio State team, then juniors at the time – excluding Bobby Knight, who had graduated.

George also became a NCAA All-American, as part of the 1962 NCAA Champion Bearcats again in the championship game victory over the same Fred Taylor Ohio State Buckeye team, then seniors at the time. After graduating from the University of Cincinnati with an education degree in 1964, George rejoined his close friend, the NBA great Oscar Robertson, and former New York Knicks great, Jerry Lucas, on the 1964 then-Cincinnati Royals of the NBA. From 1964-71 George went on to play seven seasons in the NBA for various teams, including the Chicago Bulls, the then-Seattle Supersonics, Philadelphia 76ers, the first Phoenix Suns team, and the then-Buffalo Braves, averaging 5.4 points per game and 5.2 rebounds per game in his NBA career.

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George has been induced into Chicago’s Marshall High School Hall of Fame, the Chicago Coaches Hall of Fame, the Illinois High School Hall of Fame, the University of Cincinnati Hall of Fame, the U.S. Olympic Hall of Fame, the Greater Cincinnati Basketball Hall of Fame, the Ohio Hall of Fame, and most recently in 2008, the Chicago-Land Sports Hall of Fame.

Our family’s pickup basketball legacy does not end here.

George’s son, Derek Wilson Sr., my stepbrother, who is currently living in Luxembourg, also was raised in Cincinnati, a 1985 graduate of Walnut Hills High School. Following graduation he earned a full basketball scholarship to Coastal Carolina College, playing for Coach Russ Bergman. At Coastal Carolina, he was named to Playboy magazine’s All-American Team (1988-89) during both his junior and senior years (also being named the Playboy magazine’s Anson Mount Scholar Athlete of the Year in 1988). Following college, Derek played professional basketball overseas in both South America (in Uruguay, Argentina, and Brazil) and Europe (in Luxembourg).

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Photo Credit: Playboy Magazine’s 1988-1989 ALL AMERICA TEAM: Left to right, top to bottom: Derek Wilson, forward, Anson Mount Scholar/Athlete, Coastal Carolina; Mark Macon, guard, Temple; Glen Rice, forward, Michigan; Sean Elliot, forward, Arizona; Tom Hammonds, forward, Georgia Tech; Stacey King, center, Oklahoma; John Chaney, Coach of the Year, Temple; Sherman Douglas, guard, Syracuse; Michael Smith, forward, Brigham Young; Charles Smith, guard, Georgetown; Todd Lichti, guard, Stanford

George’s grandson and Derek’s and Daniele Wilson’s son, Derek Wilson Jr. (nicknamed “DJ”), has grown up to become a 6’5” shooting guard, including versatilities as point guard and small forward, for his Luxembourg high school, LCD Diekirch. Leading his team in scoring (at 22.7 points), rebounds (at 8.5) and assists (at 4.3) in 2009, DJ represented Luxembourg in the U20 European championship in July 2009 in Macedonia. He was the second youngest competitor in the international field of basketball players, which included more than 200 players from more than 15 European nations.

Now that’s a global pickup game for DJ.

Born in 1991 and raised in Luxembourg, Europe, DJ has both an American (by his father) and Luxemburgish (by his mother) passport. He’s an excellent student, scoring a 1550 on his SAT in May 2009, and he speaks and writes in four languages fluently (English, German, French, and Luxemburgish). He has three younger brothers Jamal, 16, Malik, 14, and Isaiah, 12.

And now our family’s pickup basketball legacy continues onto the new generation.

My lovely niece, Nailah Edwards, daughter of my delighted sister, Brenda McGee, was a center-forward and point-guard basketball star for the Mount Washington Middle School Mustangs, and she was a standout teammate for The Cincy Tigerette, an AAU-sponsored select team from Cincinnati-wide middle schools. Nailah’s most notable basketball achievement has been top rebounder and her nickname is “Dunkin,” because she regularly rebounds the ball and quickly runs back and dunks it in her team’s basket. Wow.

And remember, dunking the ball by me is simply hilarious.

So, you can see why I so admire George, Derek, DJ, Nailah, and Chris. They really can play pickup with ‘The Boss‘ and even dunk the ball with him too.

I can only watch them all play pickup. But, I do appreciate hearing about their achievements in the pickup game too.


Playing a Pickup Game is as much about what is not being said than what is.

“After our game we all hung around with President Obama, who provided us with a great meal and an awesome tour around Camp David,” Chris recounts. “The President is a great mentor, as he gave me some personal moments and great advice on planning forward in my life.”

“I found The President to be very approachable and relaxed in socializing and talking with us like one of the guys,” recalls Chris fondly, “it was more than a fun day, I can’t say enough about it.”

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Listening as Chris recalled his wonderful story one cannot help but to immediately like him, as many of us cross-fitness enthusiasts at our private exclusive Georgetown gym do. I also thought as I listened to Chris’s unique perspective and take on his life-changing moment at Camp David that there is something humbling about playing ‘5-on-5 pickup’ basketball with the most powerful man in the world. This is what makes the White House such an exceptional institution respected around the world. The White House is extraordinary, because it is so ordinary for all of us.

Although I have been inside the White House, I have never been to Camp David. Yet, I find myself possessing so much pride in Chris, my friend, having been given the opportunity to be there already at his tender age so soon just beyond 22. Camp David, as Chris and I believe, is such a place of relaxation and humility for brokering any high-stakes game of pickup.

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We all can indeed be most extremely proud of The President for giving to Chris – at such a tender age beyond 22 – an experience that will transform his life. For Chris now knows what’s possible for him – the power of communication in a pickup game with ‘The Boss.’ And as his friend, I am truly rejoicing in that for him.

This is what makes such power of communication in the age of Obama, so unique and unusual to so many Americans in these times of our history. When it is as much about what is not being said than what is. Or, as much about what people are saying to each other or are not saying.

According to my in-house expert, my stepfather, George, in pickup basketball it is all about the art of the game – “where not much gets said, except where to be, who to box out, who’s shot to block” – including Obama’s humbly for Chris. Most of all, pickup basketball is all about “where the ball is,” says my stepfather. “The pickup is also about the physical squaring up, the pick and roll, the quick crossover move, the head fake and round-under, and then the “open shot” or “lay-up” or “tip-in” or even an occasional ‘dunk’ – altogether leading to just two points,” counsels George. “And then quickly you get ready, get set, launch your defense, and try to do it all over again, once you go up and back down the court.”

Sounds a lot like the risk and uncertainty of the American experience, right?

President Reagan was fondly known as “The Gipper” – who went for it all, most of the time throwing the touchdown pass for six points.

In the pickup that’s three baskets. Or, for a swingman guard-forward like Chris playing against President Obama, that’s two “sharp-shooting” three-pointers.

President George W. Bush, in contrast, was more focused on throwing the strike, but sometimes he threw a ball – and domestically that ball at times hit the dirt for no points at all.

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For President Obama it takes an individual focus – “a zone sort-of-speak,” says Chris – and a calm patience to consistently make two points at a time each trip he takes up and back down The Forum – that is, Congress – in ‘finding the votes that fits the fuss.’

Sometimes you get them. Sometimes you don’t.

And the pickup and floor leadership here is really once again, as much about what is not being said than what is, or about what people are saying to each other or are not saying.

Nonetheless, it is the eloquence of the endgame in the pickup that matters most.

The win achieved in the game is oftentimes only by a basket. Inasmuch as, the two teams logged into history, separated as winner and loser, is oftentimes determined by a slim margin of just only one or two points. On rare occasions, a margin wider than that becomes a ‘blowout’ – or a landslide.

The age of Obama understands this art of the pickup. This was the anatomy of its biggest win – The White House.

“This happens all the time throughout history,” Obama says to ABC’s Barbara Walters on November 26, 2010 in calmly responding to her questions.

No Drama Obama’ is as cool as his pickup game text message to Chris, “The Boss Wants to Play Pickup.”

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White House Photo. President Obama reaches over the shoulders of 6’9″ Bill Russell to present him with the 2010 Presidential Medal of Freedom during a ceremony in the White House East Room.

Basketball is an inner circle of five with no single leader in a pick-up game. Average teams have little to no leadership and no plan just everybody is attempting to score. Football is an organizing cabinet of twenty-two, and there is always a quarterback – where the process temporarily pauses, while the next strategy is planned before the next play resumes. There is a difference in the object of each game. Basketball is individual management for team leadership, whereas football is team leadership for individual management – the glory and the grief falls onto the shoulders of the quarterback and his decision-making.

This is what we recently laid claim to The “Tebowing” Effect.

Essentially, we want this in our business and government leaders. We want our executives to be team quarterbacks not just individual dunkers. The Boss Wants to Play Pickup is more about how our American experience can perhaps focus too much on picking up issues, but not enough on why or what we should be focusing on.

Likability is an art of our picks.

Chris and I, in our discussions about this, of course, can see why Obama likes to play pickup. He signals to us his passion each spring during March Madness. It also reveals a little something about the intimacy of the man outside his prominent role in the American experience.

What can be said by people in the midst of what is not being said is we should take some comfort in The President’s sense of intimacy in his presidency. This is what is underlying The President’s consistently high likability personally in all the tracking polls on his game.

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Chris, my friend, possesses a similar likability as The President, which, through a pickup basketball game, has awakened the true secret of his future promise and potential in life. And for this, The President is a good man.

I am honored and humbled to share in Chris’s life transforming pickup basketball moment with ‘The Boss.’ For Chris can now truly see what’s possible for him. And for that, this is good for this young man.

Like most college athletes I have worked with, Chris is not planning to chase the professional ‘sports star’ dream after graduation. He currently serves the federal levels, as a post-graduate intern on information and security technologies. But like The President (whose brother-in-law Craig Robinson is former basketball head coach at Oregon State, and whose Secretary of Education, Arne Duncan, is an ‘old hoops buddy’ Chris also played with at Camp David), Chris expects basketball to remain a big part of his life for as long as he can drive the lane (with whoever wants to be in the lane with him, including a sitting president and a cabinet secretary).

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Chris, like The President, will go far too. I like to think The President saw this in him, like I have in mentoring him.

I wholeheartedly agree with how Chris has conveyed in our conversations, as to how he has attempted to make major social impacts through his academic experiences and professional development. His contributions to the community will always remain with him, as a guiding principle of his undergraduate education and NCAA basketball playing experiences.

This guiding principle, I can attest Chris has gained from his pickup basketball game at Camp David, is increasing the public’s understanding of intimacy and humility in leadership for the good and benefit of our American institutions of family, church, schools, government, businesses, philanthropy, and communities.

I have spoken to Chris on several occasions regarding his future plans and each time I have come away with a real sense that he is firmly grounded toward reaching his goals in service to our country now. Furthermore, he is crafting a clearer and definitive plan towards completing his training to do so, the first step in his calling towards making a real difference.

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I have often expressed to him that I believe he will make a fine Congressman. He has an individual sense of people as much as his sense of the issues important to our lives, a quality I firmly believe is an early prerequisite for one to be successful in a political career, like The President.

I think Chris’s acceptance of the opportunity of presidential pickup basketball is one transforming moment that may launch his quest along his future professional career path.

I believe young people should be more exposed to outstanding opportunities that encourage them not only to pursue careers in public service, political-economic sciences and technology. But also, encourage young people to provide a good life and a good society for us all. Chris has exhibited the future promise and innovative ability to lead in this national effort and to represent his generation in a truly outstanding and positive way. In addition, he has showed early evidence that he is able to address tough questions we all face in these times. He has a genuinely creative and unusually penetrating mind and his judgment is extremely sound.

Sounds to me like a good pickup basketball player and floor leader in a good life for a good society.

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Like young George Wilson then in the early sixties, Chris is a similarly remarkable scholar-athlete and young man now. He is among the best scholar-athletes I have had the unique pleasure to mentor during my life and that I fully expect to see that he will indeed go far like so many scholar-athletes do.

I hope that you will agree with me about the quality of this fine young man’s story at Camp David playing pickup with ‘The Boss.’ I am especially gratified by President Obama for affording him the opportunity to socialize at Camp David, and to further Chris’ commitment to not only his higher education, but also his love for pickup basketball – and “more than a fun day” with ‘The Boss‘ and ‘the secrets of his service.’

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