ONE OF MY favorite conversation starters with students is to ask them about basketball.

After nearly 30 years working in schools, I’ve discovered there are few better ways to build a relationship with a middle school kid than asking, “Who’s your favorite NBA player?” — and then peppering them with questions to make them defend their answer.

Sometimes I’ll point them toward the two large images of NBA players that are on my office wall: Bill Russell and Jaylen Brown.

The educator in me can’t resist giving my own evidence for why they are two of my favorites.

I explain that they’re on my wall not just because they were elite, championship-winning basketball players; they did something bigger with their greatness.

Bill Russell used his platform to fight for civil rights and to advocate for better opportunities for Black children in Boston at a time when doing so came with enormous personal cost.

More than half a century later, Jaylen Brown has become one of the city’s most visible champions for young people, investing in STEM education, entrepreneurship, and efforts to close Boston’s racial wealth gap. From the day he arrived in Boston, he has never fit the typical mold of a star athlete. He’s as likely to be discussing social issues or economic policy as he is his latest stat line. He has also challenged sports institutions like ESPN and Nike when their practices didn’t align with his principles.

When told at the right moment, to the right student, those stories stand a chance of shifting how a young person thinks about an athlete, a role model, and perhaps even themselves.

Last week, The Boston Globe ran a compelling essay arguing that the Celtics actually won the Jaylen Brown trade. The author leveraged a dizzying array of advanced statistics—on/off numbers, adjusted plus-minus models, lineup efficiency metrics—to conclude that Brown has long been one of the league’s most overrated and overpaid stars.

The hoops nerd in me found the stats fascinating.

But as I finished the piece, I couldn’t stop thinking about a different question.

What if we’re measuring the wrong things?

Working in schools has taught me something every educator eventually learns.

The things that matter most are often the hardest to measure.

To be clear, I love analytics, and I’m no stranger to using them to try to win a good argument about the NBA. Like most basketball fans, I’ve spent years poring over stats to reveal truths that my eyes can’t always see.

It’s no different in my day job. Like NBA general managers, school leaders need every available tool to help them make better decisions.

But spreadsheets don’t tell the whole story.

Even on its own, the statistical case against Jaylen Brown isn’t as definitive as it first appears.

Yes, the Celtics won at a higher rate when Brown didn’t play – but then again, he almost always does.

For nearly a decade Brown has been one of the NBA’s most durable stars, available for roughly 85 percent of his regular season games, and 95 percent of his playoff games, despite carrying a heavy workload on both sides of the ball. That means the sample of games used to measure the impact of Brown sitting on the sidelines is remarkably small compared to most players.

Moreover, those short-term absences weren’t random. Many came because the Celtics wisely rested him against weaker opponents – the kind of teams that deep, championship-caliber rosters can dispose of with or without their stars on the floor.

There’s also an inherent limitation in just looking at the impact of one player.

Basketball isn’t boxing; championships aren’t won by assembling the five players with the best individual metrics. You win by finding players whose combined strengths create competitive advantages that overwhelm their opponents.

The Celtic’s secret ingredient wasn’t Jaylen Brown, and it wasn’t Jayson Tatum.

It was Jaylen Brown and Jayson Tatum together.

Since Jayson Tatum joined Jaylen Brown in Boston, no partnership has been part of more postseason victories. The Celtics have won 77 playoff games in the Jays Era, a cavernous gap between them and the next closest team, the Golden State Warriors with 57 playoff wins.

By asking only, “How valuable is Jaylen Brown?”—as if he existed in isolation—we’re asking the wrong question.

We’re trying to evaluate one half of the most successful on-court duo of the past decade.

Which brings me back to the two photographs on my office wall, and a feeling that I still can’t shake that something important is missing.

Why is impact on a community completely absent from this conversation?

Professional sports franchises don’t exist in spreadsheets; they exist in cities. And they depend on communities, like the one at my school, where we wear their jerseys, consume their media and contribute tax dollars from our paychecks to build and protect their arenas.

Shouldn’t we care, at least a little, about what a franchise player gives back?

It’s understandable that modern sports franchises value what can be quantified. Billion-dollar organizations should rely on sophisticated data, including evaluating a player’s impact through the lens of economics. The NBA’s second apron has dramatically raised the costs of keeping expensive rosters together, and you can’t build a winning team without embracing and navigating this reality.

Furthermore, in today’s NBA, franchises are increasingly owned by collections of investors. Private equity firms, which were once prohibited from owning NBA franchises, now hold stakes in a growing share of the league’s teams, including the Celtics. Every contract becomes an asset, and every possession becomes another data point for assessing its value.

But when numbers become the only language an organization speaks, certain forms of value disappear—not because they don’t exist, but because they’re difficult to measure.

There’s no NBA algorithm that assigns value to the experience of a middle school student spending a week on MIT’s campus because Jaylen Brown believes aeronautical engineering should be at least as interesting as basketball.

There’s no regression analysis that captures what it means for a 14 year old to see someone who looks like them using his platform to advocate for educational opportunity.

Bill Russell’s impact on the school desegregation movement in Boston couldn’t have been captured by adjusted plus-minus either.

In schools, we have to live with these tensions every day. Test scores, attendance, graduation rates: they all matter a ton. But any experienced educator will assert that those numbers don’t tell the whole story of a child. We know there are qualities – like resilience, acceptance, and generosity, to name a few that we focus on in my school – which are harder to quantify but every bit as consequential to a young person’s future. We don’t reject data, but we’re not captive to it either.

I have to wonder if NBA teams would benefit from the same humility.

The Celtics may ultimately prove that trading Brown was the right basketball decision. Time will tell.

Meanwhile, I sure hope we don’t fool ourselves into believing that the only value worth pursuing is that which we can most easily measure.

This fall, another student will wander into my office and see the same two photographs on my wall: Bill Russell and Jaylen Brown. Only this time, Jaylen will be wearing a Sixers jersey.

Maybe they’ll ask, “Why is he still on your wall? He’s not even a Celtic anymore.”

I’ll tell them what I’ve always told my students. It’s the same thing that Bill Russell and Jaylen Brown, separated by 60 years, both understood.

Some things are bigger than the game.

And greatness isn’t measured only by what happens between the lines.

Orin Gutlerner is executive director of Bridge Boston Charter School.