Interested in shorthanded offshore sailing? Go for it, and consider what it takes to get you prepared and, ultimately, successful.

The best way to better know a teammate is to

set sail and let the conversation flow

The dialogue on board Courageous during the most recent 12-Metre World Championship is terse as we maneuver around eight swift but heavy yachts at the leeward gate. My role as tactician is to guide our helmsman, Art Santry, safely through the traffic. With the cacophony of the headsail being hoisted and the spinnaker being gathered on the foredeck, Santry is quiet and hyperfocused. Somehow we round the mark with speed and pass two boats. Best of all, we’re headed toward a favorable wind shift. He doesn’t break a sweat, nor does he display any emotion. He simply concentrates, an amateur helmsman steering a fine groove like a pro.

Santry’s ability to concentrate in such a high-pressure situation comes from a lifetime of racing on a wide variety of dinghies and offshore yachts, crewing alongside some of the best sailors in the world. Leading up to the 12-Metre Worlds, I sailed a lot of hours and many races with Santry, and even with all that time alongside him on the boat, I never truly got to know what defined him personally and professionally. It happens with big teams so singularly focused on winning: It’s all business most of the time—practice, race, recover, repeat.

But I was always curious and keen to know him better, so this past summer I invited him for an afternoon sail on my Hood 32 Whirlwind. Just the two of us. The sailing, of course, was great—a long upwind cruise up Chesapeake Bay, followed by an exhilarating spinnaker run home. Over nearly seven hours of sailing, our conversation covered a lot of ground, and it was clear to me by the end of our little adventure that he spends a great deal of time thinking about the sport and how it’s affected his life and career.

His first recollection of sailing were outings aboard his uncle’s iconic New York 50, Pleione, off Marblehead, Massachusetts. He spent his formative summers in Indian Harbor YC’s junior program on Long Island Sound, and one summer at Eastern YC’s junior-run Pleon YC in Marblehead. Back then, he raced O’Day Widgeons, Blue Jays and Lightnings, and in the offseason, he was an excellent athlete who would go on to play both hockey and lacrosse at Hobart College. It comes as no surprise that he is a passionate fan and season-ticket holder of the Washington Capitals. During his late-teen and college years, he got to know Ted Hood, who occasionally sailed aboard Pleione and built sails for the boat. When Hood was organizing his America’s Cup team for the 1977 defense, he recruited Santry as a grinder. He took a year off from Hobart for the campaign. After college, he worked on an offshore oil rig for a few years before getting an MBA at the Tuck School of Business at Dartmouth College.

His experience racing in the America’s Cup trials on board Independence served him later in life. “Being a grinder was the best job on the boat,” he says. “I learned a ton because I could watch everything. You are the eyes and ears of the foredeck guys. If you see something wrong, you can see it and fix it. I learned a lot about match racing and the feeling of the boat under my feet that summer. I often tell people that that was when I really learned to sail. When you do an America’s Cup campaign, you know a heck of a lot more by the end of it.”

Teamwork, he adds, was the most important takeaway from the experience. “Independence wasn’t the boat that Courageous was, but having a two-boat program where we beat each other up, I think was invaluable to Courageous beating Enterprise,” he says. “The two-boat program was instrumental in Courageous defending the Cup.”

Santry’s observations extend far beyond the mechanics on board the 12-Metre, however. His father, Arthur J. Santry Jr., was the CEO of a major corporation, Combustion Engineering, and it was from him the young Santry learned the complications of running a business. The elder Santry was an active offshore racer and served as commodore of the New YC from 1986 to 1987. Art was on board for most of the Santry family’s races, and Commodore Santry was very involved with the club’s challenge for the 1987 America’s Cup. Art, of course, was privy to the inner

workings of the syndicate.

“My father and I were best friends, and he told me everything,” Santry says. “I knew everything. I whispered in my dad’s ear periodically. One of my comments was during a power play.” The original organizers of the New York YC challenge were from Texas, and had a strong influence on the campaign’s management and operations. As months passed, it became clear that there was an internal difference of opinion on how things should operate. “The Texas money they provided was about $2 million of the $25 million budget,” Santry says. “I said, ‘Give them the boat and let’s start another syndicate, because this is not going to go well if we don’t have [German] Frers design one of these boats.’ I told my father, ‘You’re not going to win, period.’ Everyone on the inside knew it.”

A firm grasp of history is powerful thing, and in advance of the New York YC’s current challenge for the 36th America’s Cup, Santry recalled the club’s 1987 failed campaign and was inspired to write a paper entitled Why the New York Yacht Club Lost Its 1987 America’s Cup Challenge: A Historical Perspective.

“I should have written that paper 30 years ago and sent it to somebody,” he says. “What amazed me was how few people at the club knew the story. This time, I wanted the leaders to know what happened so they don’t make the same mistakes.”

Santry’s 2,000-word essay is forthright in how not to run a sports team. The paper describes the damage caused by a schism between factions within the syndicate, how the choice of its designer was flawed, and the problems caused by the skipper who would not tolerate in-house competition. The campaign failed, as we know, and Santry thought there were important lessons to be shared today. At this early stage, the New York YC’s American Magic challenge seems to be going well, so perhaps Santry’s paper has been a helpful resource for the aspiring challenger.

“The America’s Cup has always had a major development component to it,” he says of the current competition in foiling monohulls. “It’s half the game. In the future, I think the boats should be a TP52 on steroids. Maybe 68 to 72 feet long, with deeper keels, and lighter. They should be tuned-up monohulls and really fast. It needs to be an exciting boat to sail and an exciting boat to watch.” He is also strongly supportive of national crews in the future: “I would love to keep the crews 100 percent national,” he says. “That’s really important to me.”

Our sail aboard Whirlwind started off in a light northerly wind, and we headed toward the towering 4-mile-long Chesapeake Bay Bridge, fighting a strong ebb current as we ate sandwiches and watched the scenery pass. Santry steered all day and seemed to be at such ease on the tiller; the boat was always sailing at optimal speed. Our sail continued north, with the goal of rounding Sandy Point Shoal Lighthouse farther up the bay. There were several cruising boats in the area, and Santry worked to pass all of them, just to make a point, as we tacked on every windshift. After rounding the historic 51-foot-tall lighthouse, we set the asymmetric spinnaker for the 8-mile run to Annapolis Harbor. Within minutes of the spinnaker filling, however, the wind died. Our return was going to take a while, but neither of us cared. The conversation flowed as naturally as the quarter wake that trickled off Whirlwind’s transom.

With the 12-Metre Worlds long past, Santry now primarily races his custom Ker 50, which he’s chartered for nearly nine years through a long-term arrangement with Oakcliff Sailing. Santry mentors Oakcliff’s young athletes by including them as members of the crew during the boat’s numerous coastal races. The boat was originally named Magic Glove and had a great racing record, but by the time Santry got the boat, it needed significant TLC. “As with any racing boat, Temptation takes a lot of work, but we keep improving her,” Santry says. “For our first race, we had only a limited sail inventory, and yet we finished second in the Block Island Race, so we knew it was a very fast boat.”

Unfortunately, the boat has been sitting on the hard this season, with no races scheduled, but Santry is using the downtime to make further improvements to the boat. “We lengthened the bowsprit 20 inches; we’re doing major keel work; and we have a new set of sails ready to go with spinnakers that have 275 more square feet than the old ones; we installed new digital displays on the mast and put in a new engine,” he says.

After I added up the likely operating costs of such a boat, I asked if the costs were worth it. “Well, we’ve done well with it,” he says. “You’ve got to spend money on the boat if you want to be competitive.”

Santry and Trina, his wife of 30 years, have three grown children: Artie, Alexa and Richie, all of whom are in their 20s. All three children have raced on board Temptation— to Bermuda and up and down the East Coast. Work demands much of his time these days; as vice chairman of Cushman & Wakefield, he works with large companies arranging their real estate needs. The family lives in Arlington, Virginia, and owns a home near New York YC’s Harbour Court Station in Newport, Rhode Island. He also serves on the boards of Oakcliff Sailing, the National Sailing Hall of Fame and the New York Sailing Foundation. He is a member of the New York Yacht Club, the Ida Lewis Yacht Club and the Storm Trysail Club.

Happily, the wind fills in from the east, and we have a fast spinnaker run back to the harbor. Curious about his thoughts on Whirlwind, I ask, and quickly realize he’s a fan. “The boat is awesome. It’s got classic lines, but the underbody is modern. It’s perfect.”

And with that, he set off on his way home, leaving me in Whirlwind’s cockpit to ponder what I’d learned about him and how special it is for all of us who spend time on the water—not always racing and weaving through a crowded leeward mark, but just making the time to get to know each other better. I know Santry would agree wholeheartedly.