Winner’s Debrief: IOD Celebrity Invitational

Tips from a world champion sailor on how to win in a borrowed boat regatta.
Nantucket IOD Celebrity Invitational
At the Nantucket IOD Celebrity Invitational, skippers bid for their top guest tacticians. College teammates Ted Moore and Chris Gould drew the world champion. Karen Ryan

It’s a noisy August night in a tent full of jackets and ties at Great Harbor YC. Fourteen champion tacticians flank the podium, waiting to learn which skipper bid for them in the silent auction. As the checks are counted for the benefit of Nantucket Community Sailing, Dawn Riley introduces us with some friendly heckling and one by one we’re paired and dispatched to dinner with the team we’ll spend the next two days with aboard an International One-Design keelboat.

I join Team ’71, anchored by Cornell sailing team classmates of that year, Ted Moore and regatta co-chair Chris Gould. They’ve brought along two relative youngsters, Skip Beck and Phil Cox, but looking around the tent, our average age is up there. There’s plenty of race experience around the table—Olympic and international classes (Ted and Chris), both the keelboat team-race and 12 Metre circuit (Ted and Skip), and plenty of IOD racing (Phil and Chris). The regatta program reminds me that Ted and Chris already won this regatta in 2016 with a guy named Jud Smith serving as their ­celebrity tactician.

No pressure. Six weeks earlier, I was steering the winning boat at the IOD World Championship in Marblehead, Massachusetts, but tonight, my throat is a little dry. I’m going back to school with the Class of ’71. And there’s a lot to learn in a short amount of time.


Teach them or let them teach me?

This is not a long-term ­relationship we’re building. After one practice start, we’ll be racing for real. How can I make a difference? For a team that’s only missed the top four once in five runs at this event, the answer comes quickly. “You trim the mainsheet and make us go fast,” they tell me. “We know how to sail the boat.”

But still, there are questions to answer and a Team ’71 ­strategy to develop.


Where to start?

Ted tries to convince himself to go for the middle of the line—and I’m a believer—but after one terrible start there, he shifts to his favorite team-race position, the windward end. He doesn’t need a tactician here. He’s comfortable carving out a spot, and wins it more often than not.

As someone who rarely starts at the boat end, I begin to see the power of starting here after a few races, especially when the beats are a mile or less. If we can be one of the half dozen boats in the front row until it’s time to tack, few competitors to our left will gain the three lengths needed to tack and cross us later. And even when we have a bad start, we can find clear air quickly on the right.


Favored side?

“The land side of the course often sees good shifts or pressure,” I offer up, dredging up memories of previous Nantucket regattas. I know this is the norm in a southwesterly, but I also recall seeing the land side pay in a northeasterly breeze. That’s what we have on the first day, shifting ­gradually east over two days. That’s another good reason to start to the right of the other boats.

How far do we go to the corner?


In this breeze, which is ­unstable, the answer is: “not too far.” It’s shiftier than we expect, and there are a few holes waiting to punish greedy tacticians who go too close to the beach. Plus, if the other side wins out occasionally, it’s better to be digging back against the shift early to stay in touch and try to salvage a midfleet finish. More often than not, our strategy provides modest gains and minimizes losses, a key to doing well in this event.

heavyweight IOD
The heavyweight IOD requires a steady hand on the helm and an open lane off the start. Ted Moore’s guest tactician sets them up for a clean getaway (sail No. 3). Karen Ryan

How early to the lay line?

In heavy boats, we learn the hard way that taking transoms and getting to the lay line early is vital at the first, crowded mark-rounding of each race. The port tacker who takes our stern 200 yards from the weather mark will likely have our number at the lay line. We don’t want to be the boat that tacks to leeward and tries to squeeze around the mark with half a dozen other IODs rumbling up the starboard lay line.

Quick jibe after the weather mark?

In a 15-boat fleet, ­especially with an offset mark at the weather mark, the traffic and wind shadow from boats rounding behind usually clears up quickly, minimizing the initial loss of an immediate jibe. I’m a fan of the move for several reasons:

Keelboats such as the IOD go nearly straight downwind in 8 knots of breeze, and we can often jibe and aim straight at the mark while those on starboard tack sail higher, protecting their air. When things settle down, we often find an extra sliver of wind on the edge of the fleet that allows compression with the lead group; sometimes there’s a couple of extra knots and a nice big passing lane. In this regatta, the early jibe has the major bonus of setting us up for the inshore gate.

After two races on the first day, we’re solidly midfleet with a 5-12, but we’re figuring out our strategy and we hit our stride as the breeze eases to 12 knots. We’re starting better and passing boats regularly. Suddenly, Team ’71 hits overdrive and we win two races in a row.

Upwind, point or foot?

Ted’s head stays mostly in the boat, monitoring how the boat feels, giving feedback and glancing at the compass heading. The rest of us look at the sails, keep track of other boats and assess the wind across the course. Ted and I talk quietly, sometimes incessantly. He wants to point higher. I want to go faster.

“Take me up,” he says every time there’s the slightest pressure increase, and I nudge the traveler to weather, or Skip and I trim in the sheets a click.

At the slightest pressure decrease, I suggest, “Let’s keep the bow down.” If Ted doesn’t debate the point, we slip the traveler an inch or ease the sheets slightly.

After a while, I realize Ted has mastery on the high side of the upwind groove. I start to resist the urge to suggest sailing lower. If we can keep the pace, why give away height? We’re often going faster and higher than boats nearby.

In heavy boats, we learn the hard way that taking transoms and getting to the lay line early is vital at the first, crowded mark-rounding of each race. The port tacker who takes our stern 200 yards from the weather mark will likely have our number at the lay line.

Ted starts calling me “­doctor” because each time he complains of an ailment, I’m ready with a prescription using the traveler, backstay, sheets, crew weight, outhaul and halyard tensions. I can’t prove the value of any single adjustment, but all of us are feeling good when our patient is healthy.

“Do your job.” It could be straight from a Bill Belichick playbook. We’re in the zone on the first day, but after a fog delay on the second, we start at the leeward end and finish in double digits.

Ted shrugs it off. “Let’s go back to what works,” he says, and moves up the line to nail the windward end at the next start. Our maneuvers are crisp, and we regain our speed mode, going fast and sticking with the strategy we’ve built.

Most of us must be really focused on our jobs because we don’t even notice when the regatta leader sails a throwout in the second-to-last race. Ted doesn’t say anything, even though he admits later he’s ­running the numbers in his head.

The breeze is modest for the final race, and we sail a good first beat, rounding in the top three. We move up to second on the run and close to the leader. On the second lap, the two of us are out in front and extending when we realize all the other contenders are in the back half of the fleet, sailing another throwout. We’re about to win the regatta.

The good chemistry in our crew leaps up several notches, and Phil is ready to take a team selfie at the finish with all but one boat showing in the fleet behind us. Ashore, we learn that we’ve won by 6 points, which seems massive.

“We sailed steadily, and we blended well as a team,” Ted says a couple weeks later on the phone. “But the real reason we won is everyone else had two bad races.”

I resist the urge to remind him we had two bad races too, but I’ve absorbed the Class of ’71 lesson plan: Sail fast and don’t look back.