129 Years of Boston. 10 Lessons from Jack Fleming.

Jack framed his entire role at the BAA through a single lens: stewardship. Right now, somewhere in San Diego, there are probably a couple of 10-year-olds who will run the Boston Marathon in 15 years. They haven't heard about it yet. And at some point between now and then, they will — and they'll start putting it on their bucket list. Jack's job is to make sure the race is still worth putting on that list when they get there.

That long-term mindset shapes everything — from how carefully they implement changes like the downhill index, to how they approach charity, para divisions, and accessibility. Nothing is done for this year alone.

When Boston introduced the downhill course adjustment for 2027, there was a deliberate choice made about language. Jack was clear: they landed on "index" or "adjustment" — not "penalty." That wasn't PR spin. It was a genuine reflection of how the BAA thinks about its relationship with the broader race ecosystem.

He compared introducing the policy to walking into a cocktail reception and introducing yourself the right way — respectfully, not by announcing your presence. The downhill races are part of the ecosystem. Boston appreciates them. The goal was to make an adjustment, not pick a fight.

Jack shared a prediction that stopped me. He believes the next great wave of charity fundraising in our sport isn't coming from obligation — it's coming from identity. The fastest-growing demographic in running is women aged 20 to 29. This generation isn't running for charity because they need a bib. They're running for charity because they want their marathon to mean something beyond themselves.

The question is shifting. It's no longer "what time are you going for?" It's "who are you running for?" And as Mike Nishi put it at this same conference — soon, not having an answer to that question will feel strange.

Jack has been a quiet but consistent leader on para and adaptive athletics — and his framing of it is simple and powerful. When you close roads, you're creating a public space. That space should be for everyone. The BAA now has seven para divisions in the marathon and five across their shorter distances, covering intellectual impairment, visual impairment, upper and lower limb impairment, and a growing range of adaptive classifications.

But he was also honest about what it takes. It's not just adding a registration category. It requires staff training, volunteer education, medical team awareness, and infrastructure adjustments. His advice: don't do it halfway. If you're going to welcome adaptive athletes, build the system around them properly — or you haven't really welcomed them.

This was one of the most beautiful moments in the conversation. Jack described a new phenomenon that emerged organically at this year's Boston Marathon — something the team hadn't planned, hadn't promoted, and couldn't have manufactured. Between 5pm and 6pm, runners who had finished hours earlier came back to Boylston Street. They lined the course three deep for the last finishers. And they cheered — loudly, genuinely, for people they'd never met.

Jack called it a newer thing. Organic. Not planned. And he can't wait to see where it goes. Neither can I.

Jack shared a study that I keep coming back to. The single biggest barrier to first-time marathon registration isn't the training, the cost, or the logistics. It's the fear of finishing last. Or not finishing at all. That fear — quiet, personal, rarely spoken — is what's keeping millions of potential participants on the couch.

His answer isn't to remove timing or competition. It's to make the support so visible, so abundant, so loud all the way to the final finisher, that the fear becomes irrational. An entire city behind you. Volunteers still cheering at hour six. Runners who finished five hours earlier coming back to cheer for strangers.

At the conference, Jack had lunch with Doug from the Flying Pig Marathon. He'd never been to Cincinnati. He left the lunch wanting to go. Not because the Flying Pig is trying to be Boston — but because it's completely, unapologetically itself. He marveled at it.

This is one of the things Jack loves most about this industry: the ecosystem isn't competitive in the way people assume. A runner who loves Boston also loves Grandma's Marathon, the Flying Pig, Revel races, and the Bolder Boulder 10K. There's no zero-sum dynamic. The more each race leans into its own personality and story, the stronger the whole ecosystem becomes.

Jack described sending his team to the Bank of America 13.1 in Chicago — not just going himself, but bringing multiple people from different departments. Because he'd gone two years in a row and come back and talked about it, and it still wasn't enough. Some things you simply cannot transfer through a debrief or a slide deck. They have to be felt in person.

His advice: when you send people to other events, bring more than one person, and bring people from different areas — marketing, operations, medical. The crossover perspective compounds the learning. And when you borrow an idea, make sure you make it authentically yours — don't just lift it and transplant it. What works in Chicago needs to be reimagined for Boston, for Phoenix, for wherever you are.

Jack's advice to younger race directors building something new was rooted in a simple question: who benefits? Not just the runners. The schools. The fire department. The police. The local businesses. The volunteers. The spectators who have never run a mile but come out every year because race day is their day too.

The BAA runs with 9,500 volunteers across eight cities and towns. Hundreds of thousands of residents — mostly non-runners — come out for marathon Monday. That's not an accident. It's a decade of relationship building, investment in the community, and a genuine commitment to being something bigger than a race.

Jack's hot take, delivered at the end of the conversation, is one I've been thinking about ever since. He believes the 10K is poised for a major comeback — and he made the case compellingly. It's not a 5K, where you can roll out of bed and get through it. It requires real training and real commitment. But it's not so long that it's intimidating to a first-timer. It has a hook: you finish a 10K and immediately think, I could double that. And then you're in.

He grew up running the Crescent City Classic in New Orleans — the Mardi Gras of running, he called it, from the French Quarter to City Park. That 10K was his entry point into everything. And he sees that same pipeline energy building again, especially as the COVID-era running boom works its way up the distance ladder from 5Ks toward longer distances.