VILAMOURA, Portugal – A dozen Yale sailors have competed in the Olympics since Luis Aguilar '57 navigated Tokyo's Sagami Bay during Japan's 1964 Games. However, only one Bulldog has sailed in three different Games, and he will become the school's fifth athlete in any sport to participate in four competitions.
 
Stuart McNay '05 will race in his fourth Olympic regatta from July 26 to Aug. 8 this summer when the games return to Tokyo.
 
McNay finished fourth at the helm of a two-person dinghy known as a 470 at Rio in 2016, while also racing at Beijing in 2008 (13^th place) and at the London 2012 (14^th) Games.
 
He had no idea where he stood among the pantheon of Yalies going to the Games until being queried for this. The architecture major has designs for a medal finish as he reflects on and learns from his Olympic experience.
 
"In 2008, my personal achievement was just getting to the Olympics. We had a hard-fought US Olympic Team trials, which we won, but we weren't fully ready for the Olympic games." said McNay, who has almost 58,000 hours on the water and over one million miles flying to events since his first US Sailing Team qualification 20 years ago.
 
At the Olympics in 2012, The veteran racer said his team prepared well, but fell short of its performance goals. In preparing for the 2016 Rio Games, McNay and his teammate, David Hughes, won many world cup medals and continental championships, but at the Games, ended with a fourth-place finish, he deemed deserving of the "leather medal."
 
"It was a tough decision to approach the Games for a fourth time, but my teammate and I felt like we had enough energy and drive to give it one more effort. We are now ramping up for Tokyo after five years of preparation... with the fifth year a result of the COVID delay. In fact, this might be the hardest games yet, because each team is a year more prepared," said McNay, who trails only William Steinkraus '48, who was in six equestrian competitions from the 1950s to the 70s, for the most Olympic Games competed in by a Yalie.
 
McNay, a two-time Golden Torch Award recipient for the top U.S. result at the Sailing World Cup, always loved boats, and he took every childhood opportunity to be on or in the ocean. He chose sailing at a multi-activity day camp and learned from an instructor who recommended to his parents that they enroll him in the learn-to-race program down the street at the Beverly Yacht Club in Marion, Mass. "I loved it there and kept going," said McNay.
 
The thought of sailing beyond the waters of the Bay State in national and international events did not enter his mind until he was a teenager, and then his coach at Yale made his aspiration a reality.
"I became aware of sailing as an Olympic sport in high school, but in college I began taking the steps towards qualifying for the US Sailing Team and eventually the Olympics. Zack Leonard '89, my Yale coach, has experience in the Olympic area. Zack was instrumental in shepherding me in the right direction to make the Olympics possible." 
 
Traveling the world also became reality. McNay, who is currently in Portugal, has competed at lakes, bays, channels, seas and oceans all over Europe. He has raced several times in China (Rizhao and Qingdao) and Australia (Melbourne, Sydney, Perth) and has been all over North America.
 
Imagine the things you would see while cruising through waters of that variety. McNay relishes the opportunities to observe marine life from above the surf.
 
"It's good luck to see wildlife! On our best training and racing days in Miami, we are amongst the flying fish, sharks, dolphins, sea turtles and manatees. Recently, we saw a Loggerhead Sea Turtle eating a Portuguese Man O War jelly fish."
 
McNay, a three-time U.S. national champion and two-time All-American, ate up his view of the Branford and East Haven shoreline with Long Island in the distance while training at the Yale Corinthian Yacht Club, but that's not what struck him most as a collegian.
 
"My experiences at Yale remain as some of my best memories. It is exciting and sometimes intimidating being a part of a group of people who are as intelligent and driven as they are. Being in that community set the stage for the kind of goals that I had as I graduated. The Yale sailing family is a group that I can always count as friends and fellow sailing enthusiasts." 
 
At the Tokyo Games this summer, he will have a view of snow-capped Mount Fuji. However, he is more likely to keep his eyes on the prize than take in the scenery and marine life. McNay, a three-time US Sailing Rolex Yachtsman of the Year Finalist, and his teammate, Hughes, are coached by former Bulldog and College Sailor of the Year, Thomas Barrows '10, also a two-time Olympian.
 
"It has been tremendous to work with him [Barrows] and grow together. We placed fifth at the World Championships in March 2021. We have a gap to close to make it on the podium and we believe we can do it with the combination of experience, hard work and a little luck."
 
The past year has been a trying period for many, but there has been some good fortune among the ruins of the pandemic. McNay and his wife, Tanya, have two children, Lexi (3) and Sammy (5). Last summer, when travel was limited due to COVID, McNay trained in New England and his kids could play on the Olympic training boat before or after the sailing.
 
"It was wonderful to able to share more of what I do with my family," said McNay, who has used the pandemic as a time to contemplate his career. "It has been a long road - a road full of lessons, rewards, and frustrations too. I am happy to have made it this far, but after this Olympics, I will be ready for a change. Also, I have promised my family that I will look for something that keeps me closer to home more often."  
 
Family has always been important to the guy who was born in Boston and now calls Providence his home. He and his parents enjoyed calling Yale home for four years enough to make a special gift to the university in 2006, when the sailing center was officially renamed the McNay Family Sailing Center at Yale University. In addition, his parents, Joe McNay and Beth Pfeiffer, endowed the operational support of the program and the head coaching position.
 
"It's an honor to have my family name on the Yale Sailing Center and to have been part of an incredible institution and its storied sailing program."
 
A great showing at Tokyo would be a fitting conclusion to a legendary career, adding to the legacy of the Elis' prolific Olympian.