I’ve always felt that if you really want to know what motivates a guy just ask his mother. So when I had the opportunity before the first day of Quantum Key West, as we gathered at our crew house for nachos, beer, and NFL playoff games, I saddled up next to our skipper Charles Kenahan’s mom, Eileen, a lovely lady with a radiant smile and a twinkle in her eye. My first question to her was of the casual sort: “So … what do you think of all this?”
She happily regaled me with stories of her son’s childhood sailing and how he used to crew on so many other people’s boats when he was younger. After a few minutes she paused, as if recalling a distinct moment in time.
“I’ll always remember him telling me, ‘Mom, someday I want to own my own raceboat,’” she said, pausing again. “I’m so proud of him.”
That last part struck me because it’s not something I often experience in the sport beyond junior sailing circles—a proud mom. Then again, I don’t find many moms hanging around crew houses either. And later that night, as I thought about what she’d said, my outlook on the week of racing that lay ahead changed. Sure, I wanted to win, or at least do well, not just for my own pride or the team’s, but for her’s, too, because pride is infectious.
Kenahan, I’ve come to learn since joining the team, is a classic self-made raceboat owner. Having sat out many sailing years to raise a family and build a career, he’s returned to the sport with gusto. He bought his Swan 42 last year because he wanted a raceboat that his family could enjoy, not a tricked-out grand-prix machine with a full-time payroll of pros. He also wanted to race with his friends, with amateurs like himself, and he had aspirations beyond his hometown PHRF fleet. Those aspirations included Quantum Key West, the one event that, despite its smaller numbers these days, still carries more cache than any other.
If it weren’t for the turquoise water, warm sun, and reliable January winds, it wouldn’t be much different than racing in a 10-boat handicap fleet elsewhere, but what sets Key West apart from other regattas is the commitment of owners like Kenahan. Delivering the boat and its trailer from New England, coordinating, housing, and feeding a team, and then turning the entire thing around and bringing it all back north is a major undertaking—for 10 races. To improve the collective skill level of the team, one must play amongst those who are equally committed, and when everyone else is just as committed, the races are that much harder to win.
Fortunately for our nascent team, light winds on the first day of racing allowed us to ease into the regatta, and after two shifty races we managed to put two third-place finishes on the scoreboard. The results earned Kenahan his first trip to the prizegiving podium later that night. He was beaming like never before as he stepped up to collect his decorative wooden box, with his young son in tow. He was proud, his boy was proud, and his mom was ecstatic.
Our performance proved to be an anomaly, though, because when the wind kicked into high gear, our collective inexperience shined. On the second day, when a white squall unexpectedly ripped through the racecourse, we hesitated to douse our spinnaker and it shredded into three pieces as we pulled it from the ocean’s grasp. And even though we were graced with the most perfect, brochure-sailing conditions on the third day, we couldn’t do anything right: shrimping, penalty turns, bad starts, bad tactics—you name it, we did it. When reality bites your pride, it stings.
We tried a little motivational pep talk on the way out on the fourth day, but we could do no better getting around the course. Our slide down the standings continued, and we ended the day with Kenahan’s words resonating in my head: “Come on guys … we’re better than this.”
As we sailed to the racecourse under spinnaker in a whipping 25-knot northerly for our one and final chance at redemption on the last day, our spirits were buoyed by the highlight of our week: topping 15 knots on the speedo. Kenahan was thrilled, his hands gripping the white wheel and a grin pressed firmly across his face. But that was the sole highlight of the day. The electronics went on the fritz, we were late, slow, and out of sorts when the race started, and as if to put us out of our misery, we shredded our last heavy-air spinnaker before we were even halfway down the first run.
“I’m not a quitter, and I’ve never retired from a race,” said Kenahan, defeated and draped over the wheel that moments ago had given him so much pleasure. “We’re doing more harm than good. Let’s call it a day.”
We’re not proud of our results, but at least mom’s still proud, and we can take pride in that.
This article first appeared in the March/April 2014 issue of Sailing World. Click here to read more from editor Dave Reed.