In 1965, John Kantor needed a summer job. He wanted to be a Longshore caddy — but was rejected.
He walked across the parking lot to the sailing school. They hired him.
The rest is history.
Longshore Sailing School celebrates its 50th anniversary this weekend. Hundreds of former employees will eat, drink, dance and reminisce about summers that were fun, fulfilling, and — for many — transformative.
Kantor has been around for nearly all of those 50 years. Quietly, efficiently — improving what works, and always changing with the times — he’s built Longshore Sailing School into the largest such youth program in the country.
By far. You might say it blows everyone else out of the water.
In retrospect, getting rejected as a caddy — and hired by the then-nascent town sailing school — was karma. Kantor grew up on Owenoke — just across Gray’s Creek from Longshore.
“I clammed at low tide, and sailed and raced at high tide,” he recalls.
When the town of Westport bought the failing Longshore Country Club in 1960, it had no idea how to turn it into a town park.
It knew even less about running a water program.
“In the very beginning it was just borrowed rowboats and volunteer instructors,” Kantor says. “John Mulhaussen took kids from what is now Strait Marina out to the channel. It was basic boating.”
A couple of years later, 8-foot Sprites — “bathtub boats,” Kantor calls them — were introduced.
1964 marked a quantum leap. Bill Mills — owner of American Fiberglass Corporation in Norwalk — manufactured Aqua Cats. He loaned a small fleet to Westport, for an advanced sailing class. It was the 1st multi-hulled sailing program in the US.
Kantor came on board the next year.
And never left.
By 1969, Longshore boasted 3 junior national Aqua Cat champions.
But, Kantor says, “The town always knew it wasn’t very good at running a sailing school.”
In fact, the Parks & Rec department ran the fiberglass boats into the ground. They never replaced any, so by 1975 the fleet was in bad shape.
A national recession was underway. “Recreation is low on most priority lists to begin with,” Kantor says. “And sailing is always low on the recreation list.”
With several hundred young sailing students each year — and a program run out of constantly collapsing cabanas near the pool — Kantor made a proposal. He’d buy a new fleet — at his own expense — provided he could keep any profit.
If there was a loss, he’d absorb it himself.
First selectman Jacqueline Heneage agreed — provided he put his name on the sailing school.
“I didn’t want to,” Kantor says. “But I guess that was a way for the town to wash their hands of it if things didn’t work out.”
They did. The program continued to grow, almost exponentially. Now, with 1,400 youngsters a year, it’s monstrous.
“And those are full courses — not 1-shot private lessons,” Kantor emphasizes. Add in several hundred youngsters, and 2,000 people learn to sail each summer.
When the program outgrew its makeshift building — but the town was reluctant to pay for a new one — Kantor formed the non-profit Friends of Longshore Sailing School. Former employees — now very successful — funded a 2-story, $400,000 structure. The school now has 5 classrooms, plenty of storage space, and an actual office.
The program also outgrew fiberglass boats.
“They were hard to maintain on a stony New England beach,” notes Kantor. “And with people learning to sail, there were always scrapes. They took beatings, and then got dragged up and down the sand.”
The move to other synthetics has been a godsend. For years, Kantor stayed until midnight readying the fiberglass for another day.
“Things were so tight, we couldn’t afford to be down even 1 boat at any time. It was exhausting.
“Now we just hose ’em off at the end of the day, and we’re done.”
Kantor has watched his business evolve in many ways. He bought Hobie Cats from the Boat Locker. Windsurfing was big in the 1980s; then kayaking was the rage.
The latest trend, Kantor says, is standup paddleboarding.
After 45 years, Kantor has plenty of memories. The best ones are of his staff.
“We’ve had over 1,100 employees over the years,” he says. Laid end to end, they would reach from the Longshore pool to Elvira’s. (Insert your own joke here.)
“There are so many very interesting, special people. We hire them as high school or college kids, and watch them grow. It’s neat — and gratifying — to see that happen, and help mentor them along.”
This Friday’s celebration of the program’s 50 years will not be the 1st. Past reunions have been drawn hundreds.
“I’m amazed that any place could have a reunion of a summer job,” Kantor marvels.
A TV producer is flying in from Los Angeles — for the day.
“They go to each other’s weddings,” Kantor says of his former employees.
Some even go to their own. Four couples have met at Longshore Sailing School, and gotten married.
A reggae band — composed entirely of sailing school ex-teachers — will play. An improv comedian — of course he worked at the sailing school too — will entertain.
Five screens will show thousands of slides.
Of course, the next day everyone is invited out on the water.
So what does all this say about Westport?
“This town is a place to raise kids,” Kantor says. “They want their kids to have access to the water, without being vetted by a private country club.
“I’ve heard that people move here because of the sailing school. I don’t know how true that is, but kids dig it. And parents are all for something their kids love.”
In 2013 — Longshore Sailing School’s 53rd year, and Kantor’s 48th — his town contract is up.
“It’s time for someone else to run this,” he says.
“I’m trying to groom my successors. I never tire of teaching — just administration. I hope they’ll hire me to work for them — as a teacher.
“I want to hand off this building, and the finances, in good shape.
“I hope Longshore Sailing School lasts forever.”