The Unyielding Love of Pickup

Pickup game rules are governed by the players. But there are always the unspoken ones.

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My teammate Kevin, an executive at Welch’s, sets a sturdy pick on my defender Chuck, a financial advisor. I dribble to the right, find an opening, square my shoulders, and launch a perfect jump shot. The ball leaves my hand in a spinning arc and ripples through the net. With a slight grin, I turn and trot back up the court as the crowd goes wild. The basket gives us the lead, which we won’t relinquish; another victory secured.

That scenario is entirely accurate—well, except for the crowd going wild. There is no crowd. It is just us, a group of guys in a small rustic gym in Concord, Massachusetts, playing our regular lunchtime pickup basketball game. Though the faces have changed over the past 25 years, the ritual remains the same. Pickup hoop is my addiction, and this year, as I turned 65, I marveled at how long I have kept at this, well beyond my expiration date, in a game I started playing when I was 12.

Back then, I would have dropped to the ground laughing if someone had suggested I’d still be playing when I was enrolling in Medicare. This is a young man’s game, after all, and running full-court for an hour or two would just be too much. I’d be injured, I’d keel over from a heart attack, I’d simply be embarrassing myself trying to dribble, leap and score on arthritic knees and bum shoulders. Against the odds, I’ve kept at it along with a bunch of guys in their 50s and 60s, who, like me, can’t give it up.

Pickup basketball has long been a staple of America’s, now the world’s, workout diet. President Barack Obama got major props for playing regularly at the White House. How cool was it that the commander-in-chief could go to his left and hit the three?

According to Statista, a statistics portal, more than 30 million Americans play basketball, up from 25 million in 2008. While some play on formal high school and college teams, the vast majority are pickup players who show up at gyms, choose sides and run. Since the famed US Olympic “Dream Team,” featuring Magic Johnson, Larry Bird and Michael Jordan, wowed the world in 1992, pickup basketball has exploded around the globe. Go to an outdoor court in Hamburg or Nairobi or Beijing and you will undoubtedly catch a pickup game in action. Don’t forget your Nikes.

In reality, basketball is far more than a fitness regimen. It is an obsession that keeps men and women out on the court for years past their athletic prime. Not surprisingly, pickup basketball has a particular appeal to business leaders. It is simple to learn but exceedingly difficult to master. It is an intense physical workout that leaves you dripping with sweat and fatigue but joyous in its intricacy and challenge. Most of all, it is hypercompetitive and without ambiguity. Every game has a winner and a loser, and if you’re good enough, like in business, you control the outcome.

Take Tom Tremblay, a tall, athletic, deadly perimeter shooter, with whom I’ve played for more than 20 years. Tremblay is an entrepreneur, the founder and CEO of Guardair Corporation in Chicopee, Massachusetts. Also 65, he has played all his life. Longevity in business, he says, tends to yield long-term success. “That’s one reason I keep running my company and I keep playing basketball.”

Besides the sheer competitive passion, Tremblay sees many analogies between running his company and shooting hoops. It’s about striving to improve and striving for perfection, Tremblay explains. “Avoiding mistakes in business is the same as avoiding turnovers and making shots in hoops,” he says. “As is especially true in business, winning is a lot more fun than losing.”

Perhaps most appealing, basketball is the perfect escape from the wearying obsession with work. “I think about my business constantly outside the office and it gets tiresome,” Tremblay says. “When I’m playing basketball, I’m concentrating 100 percent on the game. I leave my worries and frustrations on that court.”

Even after back surgery, a ruptured Achilles tendon, and assorted other aches and pains over the decades, my passion for this game goes deep, beyond logic and a doctor’s advice to try golf. What keeps me out there three times a week, chugging up and down the court, trying to guard guys half my age with twice my skill, is primal, a hunt for that perfect pass, a blocked shot, a chance to score the winning basket. Executives know this feeling, operating in a place with an unspoken code of honor, an agreed-upon set of rules, no referees and a level playing field where victory is sweet. It is tough to give up. I walk into the gym, see the basketballs, the hardwood and the backboards, and, like Jack Twist said to Ennis Del Mar in “Brokeback Mountain,” I mutter, “I wish I knew how to quit you.” I shrug, and then I lace up my sneakers for yet another game.


Pickup game rules are governed by the players. But there are always the unspoken ones.

Tone Down the Trash Talk 
Leave the insults to pros who have the skills to back them up.

Don't Call a Bunch of Fouls
Players don’t want to stop the game for every bump or push.

Stick With Loose Gym Attire
Wearing NBA jerseys can border on dorkiness. A full uniform is especially embarrassing.

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