I grew up sailing at a no-frills, middle-class yacht club in Marina del Rey — a place that, in the ’70s and ’80s, quietly produced some damn good sailors. We had no coaches, no coach boats, no rigid programs. The older kids taught the younger kids. There was no formal summer sailing program — just kids hopping in boats and figuring it out.
Tuesday nights, we raced Sabots at our club. Not Optimists — Sabots. Wednesdays, we’d walk the docks looking for a ride on a keelboat for evening racing. Thursdays, we’d haul our Sabots over to California Yacht Club for more competition. It was organic, unstructured, and, most importantly, fun.
By the time my own kids were old enough for dinghy sailing, the landscape had completely changed. The sport had been hijacked by RIBs, professional coaches, and a level of structure that made Little League baseball look laid-back. I chose a different path. Instead of shuttling my kids through a hyper-organized junior sailing program, we sailed as a family. We spent weekends at Catalina, raced together occasionally, and, frankly, I don’t think they ever set foot in the junior clubhouse or its summer program.
Then, about five years ago, my wife and I found ourselves in Miami, thanks to a client at our boutique ad agency. We got a small place in Coconut Grove and joined the Coconut Grove Sailing Club — a great, low-key spot with a welcoming membership.
One Friday night at the club bar, a few of us got to talking. We all knew about the summer sailing program, but it was packed with the same kids who were already in the junior sailing program. Sure, it was technically open to the public, but the reality? The barriers to entry were sky-high. If you’ve ever been to Coconut Grove, you know the stark divide between the “haves” on the water and the “have-nots” just inland. Those two worlds rarely, if ever, met.
We decided to change that. The plan? A fundraiser to offer scholarships to underprivileged kids so they could participate in the summer program. I stepped up, offering to donate seafood from our oyster farm and flew out my restaurant’s best staff — on my own dime — to prep and serve the food. The club’s GM, a great guy, loved the idea. The only catch? The board approved the event as long as it didn’t interfere with normal club operations. Fine by me.
A week before the event, I was introduced to a woman presented as the “parent in charge” of the junior program. She casually mentioned that it was a shame we scheduled the event when some of the junior sailors would be away at a regatta in Tampa — because, of course, they wouldn’t be there to “thank everyone for supporting them.”
I told her, point blank, that this wasn’t about supporting the junior sailors. It was about funding scholarships for kids who otherwise wouldn’t have access to the sport. Her response? “I’ll decide where the money goes after the event.”
Now, if you know me, you know I don’t tolerate bullies. And this woman? She was about to bulldoze the club into redirecting the funds to the junior program — something she made painfully clear.
I had also had a drink or two that night. My response? “We’re not doing this to subsidize a bunch of rich snobs so they can keep pushing their dream of getting their kids into Harvard via the sailing team.” She stormed off.
The event itself was a massive success. The GM lined up liquor sponsors, the food was a hit (we grow some damn good oysters), and the energy was electric. It made such an impact that the Mayor of Miami-Dade County crashed the event with her entourage, eager to support the idea of a private club on public land doing something meaningful for the broader community.
The following week, a board member pulled me aside. “This was the most significant fundraiser the club has ever done,” he said. It had raised over $20,000. He told me the board planned to formally thank me at their next meeting.
That never happened.
Instead, I learned that the “Opti-Mom” in question had conspired with her friend — the Club Manager (not the GM) — to quietly funnel the money into the general fund for the junior racing program. The board didn’t fight it. And, unsurprisingly, they never thanked me. Nor did they ever ask me to run the event again.
This is the problem with the sport today. The people at the helm aren’t interested in growing sailing — they’re interested in controlling it for their own narrow agenda. And the worst offenders? The Opti-Moms.
They show up five days a week, hire private coaches, and have zero personal interest in sailing. For them, it’s just a vehicle to get their kid into an Ivy League school. And while I don’t begrudge any effort that gets kids into boats, the problem is the execution.
These kids are drilled relentlessly from grade school through high school. If they don’t show promise, they’re shuffled out and never sail again. If they do show promise, they’re pushed to the brink. By the time they either miss the college sailing cut or graduate from a team, they’re completely burned out — and never step foot on a boat again.
We’ve lost entire generations to this machine. What do we have to show for it? Fewer active sailors. Declining Olympic results. A shortage of experienced crew, forcing boat owners to walk away. It’s a downward spiral.
No, we didn’t have the intense infrastructure when I grew up. We just sailed. Maybe we could have been better sailors. But here’s the thing — most of us are still in the sport, still passionate, still racing. Between 1984 and 1996, my generation brought home 22 Olympic sailing medals. In the last four Olympics? The U.S. has won two.
Maybe it’s time to stop trying to manufacture the “perfect” sailor and just let kids fall in love with sailing again.