On a chilly day in the mid-1930s, Erwin Schell ‘12, head of MIT’s business administration course, looked out his office window and noticed some MIT students sailing a frostbite race on the Charles. The sight inspired him. Soon after, he and George Owen, Class of 1894, who headed the Department of Naval Architecture, went to see Walter Cromwell “Jack” Wood ‘17 to discuss starting an MIT sailing program. Owen drew up plans for a boat eventually dubbed the “Tech Dinghy,” and Schell set about raising funds to build a small fleet of them. As MIT’s first sailing master, Wood then presided over that 48-boat fleet at a new pavilion, and MIT hosted its first intercollegiate sailing competition in 1937.

Owen’s design for the Tech Dinghy was ingenious, incorporating both cat and sloop rigging to maximize performance for highly skilled sailors while providing stability for novices. Although the boat has evolved–it’s now in its fifth generation–its great balance remains its defining feature. In 1953, the second generation of the dinghy hit the water, a fiberglass hull replacing Owen’s wooden one. For the third generation, Halsey Herreshoff, SM ‘60, increased the height of its sides to prevent it from taking on water; for the fourth, he heightened the mast. And in 2004, MIT sailors launched the fifth generation of the dinghy, which has flotation tanks that make it easier to right when it capsizes.

In typical MIT fashion, the Tech Dinghy has featured in several hacks–appearing fully rigged on the small dome of Building 7, in the Alumni Pool, and in the campus chapel’s moat. Institute presidents including Karl Compton, Paul Gray, and Susan Hockfield have sailed Tech Dinghies. And every year, 1,200 to 1,400 students take sailing lessons, and even more take the 37 boats now in the fleet out on the Charles.

Perhaps the most famous student sailor to take the helm of a Tech Dinghy is John Bertrand, SM ‘72, who won the 1983 America’s Cup for an Australian team, ending a 132-year U.S. reign. ­Bertrand had lost his first attempt at the cup in 1970, the summer before he came to MIT. Studying naval architecture under Jerry ­Milgram ‘61, SM ‘62, PhD ‘65–whom he has called “brilliant” and a “crazy man”–broadened Bertrand’s knowledge of fluid dynamics and tactical dinghy sailing.

“He was a crew member and a student of mine,” Milgram recalls. “I supervised his thesis. We worked one on one about how you could apply that theoretical knowledge to actual sailing. We would talk about the relationship between the hull resistance and the generation of side forces related to the force made by the sails and say, What’s the best thing for you to do after you tack, when you’re down in low speeds and you need to accelerate up to full speed?”

Bertrand remembers being surprised by the local talent on the Charles. “It felt initially like lambs to the slaughter; the local wind shifts and local knowledge were all-consuming until I started to get the hang of it,” he recalls. “The Tech Dinghy, although old-fashioned and slow, was a superb training and racing boat, since it was easy to rig and sail.

“MIT showed me many ways to think about and solve problems,” he continues. “There was a can-do mentality that was part of the culture. I also learned how to work with creative geniuses like Jerry, which was fundamental in my ability to later put together and work with a world-class group for our successful America’s Cup challenge in 1983.”

Milgram was asked to teach his legendary sailboat design course one last time before he retires this August. But he warns that the class is not all fun and games. “That’s what too many people think,” he says. “Then they come in and find out it’s a real MIT course, with real MIT learning, real tough stuff, and half of them drop out. They thought it was going to be fun, but a sailboat is a very complex system with complex engineering.”