The Patriarch and His Posse

For Tom Rich, family has always come first, and sailing is no different.
Tom Rich
Tom Rich keeps tabs on the competition in his wake at the New York YC’s Annual Regatta, with his daughter, Lori, doing the same. Michael Hanson

The seabreeze builds to 15 knots across Rhode Island Sound as Tom Rich watches his son-in-law stumble through a tack on his way to grinding in the jib. Thwack, thwack, thwack. The jib flogs in the wind. It’s the first day of racing at the 165th New York Yacht Club Annual Regatta, and with stiff competition in the IRC 2 fleet, there is no margin for error.

“Get that thing in,” says Rich as loud as he can. Rich is by no means a screamer, and for a man of large stature, he is soft spoken and patient on the helm of his Tripp 43, Settler. Though he always races to win and could recruit plenty of pros, Rich makes a point to sail with his two daughters and a growing list of in-laws, so for the crew of Settler, sailing has been, and always will be a family matter.

Rich, of Portsmouth, Rhode Island, says his father started the Settler program when he was in high school. Over the years, the family fleet included a C&C 33, a New York 36, and a Peterson 42, all called Settler. The boat’s name is a nod to the family’s heritage. “My dad always said our family was related to the original founders of the town of Southold on Long Island, one of the first English settlements in New York in 1640. So we thought the name was appropriate, particularly because settlers are typically the first ones there, so for a race boat, it makes sense.”


As former co-owner of New England Boatworks, Rich has worked on or built countless raceboats around the Rhode Island area. NEB built Settler in 1996, and Rich bought it in 2013. “It was important to have a boat that we built,” he says. “Since then, we’ve monkeyed with it a lot. We put a TP52 keel on it. We modified the rig for mast head chutes. At the end of the day, it’s a fun boat, but it’s not all that competitive.”

For the Annual Regatta, Rich brings on new recruits for two days of racing in the ocean off Newport, filling gaps between his regular crew: daughters Abby and Lori, as well as his son-in-law, Alex. I am assigned to the mainsail, and as I watch the wind increase to 20 knots, I remind Lori, who manages the pit, to have a hand on the vang for mark roundings and bearaways. She turns around, raises an eyebrow and gives me an “are you seriously telling me this” kind-of-look.

“Don’t worry,” she reassures me. “I’m well-trained.”


Lori and her older sister Abby have been sailing on some rendition of Settler ever since they could walk. “There’s photos of my sister and I on the back of the last boat with our grandfather, who used to trim main when we were kids,” Lori says. “As we’ve grown up, we’ve been promoted up the ranks. By now, most of the crew work is automatic for us.”

On an older boat like Settler, with a symmetric spinnaker and a long carbon pole, the pit is a critical position and Lori performs true to her word. Throughout the weekend, not a single line is fouled or a single maneuver mistimed. Abby, is equally skilled as a spinnaker trimmer. Between races, she sponges out the bilge, provides sustenance to the crew, and double-checks the spinnaker gear—all habits of a veteran. During the races themselves, Abby’s communication is clear, her mechanics are sound, and the boat itself makes it through the day without any hangups.

And then there’s Alex, Lori’s husband of two years, who’s one job it is to hammer away on the winch as the headsail pulls into place after every tack. “For the first year, he was trying to stay on the boat more than anything,” Lori later admits. “It’s been a steep learning curve for him, but he knows it means a lot to the family.”


Alex went from never having stepped foot on a boat four years ago to being a full-time Settler crewmember. Though he’s still a bit green, he has a great attitude. He isn’t afraid to ask questions, and is always quick with a joke when things get too drab.

As we finish out the day and make our way back for a drink at New York Yacht Club’s Harbour Court, Rich’s original assumption about how the boat would perform comes true. We’ve had a fun time, but ultimately, there’s no sense in looking at the score sheet too closely.

“It’s tough because dad really likes to win,” Lori says. “There was one year with the old boat that we won every race. It was the year the [New England] Patriots went undefeated. And then when they lost the Superbowl, the joke on board was that we were better than the Patriots that year.”


The Patriots have their dynasty, as does the Rich family, but for today’s Settler crew, the goal is simply to do well, race hard, and have fun. With grandchildren entering the picture, Tom, the patriarch, anticipates another generation of settlers destined to take up a winch handle or sheet one day, and the tradition continues.