The Bitter End YC’s Pro-Am regatta began nearly 25 years ago as a marketing campaign. It has evolved into a fall classic. In November, I was one of seven “pros” invited to spend five days in the British Virgin Islands sailing IC24s, which are essentially J/24s modified with a more crew-friendly deck and cockpit layout—perfect for this application. This year, we had three days of fleet racing and a final day of match racing to determine the winner. There are no spinnakers, but throw in the reliable trade winds, and there’s lots of action.
What makes the regatta unique is that the resort’s guests make up the crews: young and old, talented and novice, female and male. Most guests come specifically for this event, for the opportunity to sail with famous sailors in an idyllic location. All are extremely enthusiastic. It’s an aquatic version of “Field of Dreams”: “If you build it, they will come.”
I’ve been 14 times or so. Every year, the format is a little different.The event has utilized fleet racing, match racing, and team racing. There have been veteran divisions and junior divisions. We’ve sailed Freedom 30s, IC24s, and Hunter 21s.
On my very first visit, 22 years ago, we sailed the resort’s fleet of Freedom 30s. I was one of the youngsters in the group, and it was a big event for me for one very specific, non-sailing reason. I brought my girlfriend, Kathy, and had a plan to get engaged at the regatta. She had no idea. Needless to say, there was a little stress outside of the sailing that year. I remember fleet-racing against the likes of Buddy Melges, Tom Blackhaller, and John Bertrand. Peter and JJ Isler, and Terry Nielson, were there, as well. We were all pre-children, so the rum was flowing when the racing wasn’t happening.
One particular race stands out, and I wasn’t even involved. Buddy and Tom were match-racing in the round robin to determine the finals, and Buddy was about five feet behind at the final leeward mark. All of a sudden, Buddy started screaming at the judges, “He has his engine on!” Tom looked at Buddy, then at the engine controls, then to the judges, and said, “Holy crap! It is on, and it’s in gear!”
They were really quiet diesel engines, I have to add. But Tom had done a lap and a half with his engine on, and in forward. How he was only ahead by a few feet, I’ll never know. Instead of pitching Tom from the race, the judges decided to re-sail it. That’s the spirit of the Pro-Am: Nobody gets thrown out; they just get a “do-over.”
I was pretty new to match racing at the time. Somehow, I made it to the finals, up against John Bertrand, who’d been doing a lot of match racing. John jumped out to a lead, but I clawed back to round the final mark about a foot from his transom. I started a tacking duel, which made two pretty slow boats go even slower. I think I took six inches out of that lead, but it was enough that John broke off the duel and let me get to the unfavored right side, where I tripped over a small rain squall that shot me to victory. Better to be lucky than good. On the dock afterward, John said, “Kenny, you should do more of this match racing. You’re pretty good at it.” That statement meant a lot to me and has stuck with me for a long, long time. And, in case you were wondering, on the second-to-last night, Kathy said yes.
This year, in addition to me, the cast of pros included America’s Cup vets Russell Coutts, Paul Cayard, and Peter Holmberg, and 2008 Olympic medalists Anna Tunnicliff and Zach Railey. Stuart Bithell, England’s top-ranked 470 sailor, rounded out the group. He won the British equivalent of the Championship of Champions to earn his invite.
We fleet-raced for two and a half days, and the top four qualified for the match-racing portion. As always, the amateurs on each boat are chosen at random. Getting the crew on the same page in a short period of time is one of the biggest challenges of the regatta. I usually cover tacking and jibing procedures, and choose who will be winging the jib. As soon as you start to gel as a team, they swap the crews around, and you start all over. It’s really a huge part of the fun.
This year, Russell won the fleet racing and first seed in the match racing. I was second seed, Peter was third, and Paul fourth. Peter kicked my butt in two straight, then dispatched Paul in the finals. He was clearly the only person who’d been practicing match racing lately.
Where it really got interesting was during the consolation final between Russell and myself. It was just after lunch, we each had new crews, and the breeze was up. The first race was uneventful: we started just to leeward, caught the left shift, and held on for the win. During the second starting sequence, we lost track of the time and entered the starting box exactly one-minute late. This allowed Russell to sail across the starting box, tack to starboard, and angle up at us hoping to prevent us from officially entering the starting box. Not good. As he approached the committee boat on a closehauled course, and we sailed in nearly planing on a broad reach, I saw a sliver of an opening between Russell and the committee boat. We crash-jibed to port, threading the needle between Russell’s weather side and the committee boat with inches to spare, half our crew dragging in the water and half in a stunned silence.
Russell decided to top our bizarre move by immediately spinning the boat into a jibe in order to get on our transom. Problem is, he forgot to warn his crew and flipped the boat on top of the six-person team sitting on the windward (now leeward) rail. It was an amazing sight, that little J/24 keel wagging in the breeze while the team struggled to get to the high side. And what did we do? Watched in stunned silence.
We were so preoccupied in watching our competition drowning his crew that we completely forgot that our starting timer was a minute behind. By the time we remembered and jibed back toward the line, we were too late. The boat that capsized in the pre-start righted itself and beat us across the line by 30 seconds. It wasn’t pretty. But at least the spectators on the committee boat have a story they can tell for a long time.
After we split the first two races, it was unanimously decided that we call it a day and proclaim our series a tie for third. We needed all the guests to get back to the club alive and in one piece.