When Will Cleary '22 was growing up on the Loomis Chaffee campus, his favorite thing to do in the fall was watching the soccer teams in the Meadows. 

“I thought the players were so old, so good, so cool,” Will said recently. “I wanted to be like them. I looked up to them so much and thought I didn't know if I’d ever be good enough to play for Loomis. They inspired me so much. So then the goal was to work hard enough to put the Loomis shirt on.” 

He not only put the LC shirt on but was captain for two years. He then put the Stanford University shirt on and was captain there as a senior. And now he wears the Charlotte FC shirt in Major League Soccer. 

“I always had a lot of pride playing for Loomis and wanted to push to be the best I could be,” Will said.  

That desire to give it his all not only spilled over into other sports — but in all aspects of his life at Loomis. He earned 12 varsity letters (four each in soccer, basketball, and lacrosse). As a junior, he received a Founders Prize in recognition of his scholarship and citizenship. As a senior he received the Sellers Faculty Prize, given for personal achievement and service to the LC community. He graduated with cum laude honors. Will’s accolades on and off the pitch continued at Stanford, ranging from being named to the United Soccer Coaches All-South Region first team to earning College Soccer Coaches first-team Academic All-America honors.  

So it might come as no surprise that in his first MLS start on May 23, he was named Man of the Match, given to the player judged the most outstanding player in the game. Will completed 34 passes and assisted on the game’s only goal as Charlotte beat New England 1-0 in North Carolina. Will was selected 22nd overall by Charlotte in the 2026 MLS SuperDraft. 

Will’s parents, Director of Admission and Financial Aid Nancy Cleary and math teacher Joe Cleary, were both college athletes. Nancy played volleyball and basketball at Williams College. She scored 1,472 points and had 962 rebounds in her basketball career and was inducted into the New England Basketball Hall of Fame in 2015. Nancy’s father, Bill “Moose” Hedeman ’54, played basketball and at Loomis Chaffee and at Williams. Joe played soccer and lacrosse at Siena College and still plays in a men’s league. 

Will texted his parents the night before the New England game saying he thought he would be starting the game. They flew down Saturday morning. So did an aunt and uncle. It was a day the family won’t soon forget.  

“There was a lot of joy, happiness, pride, and getting to see my family really brought out the emotions even more,” Will said. “For me, I’m always trying to move forward. That was a great day, a great moment, and I'm glad I got to share it with my family, and now it’s how do I make [starting] a more consistent thing?” 

“This has been his dream since I can remember,” Nancy said. “For him to step on that field and reach that ... it was super emotional, as you can imagine.”  

Commencement at Loomis Chaffee was the next day, Sunday, May 24. Being back in time for Commencement was important. Nancy had multiple advisees graduating, including the Class Speaker, Max Shactman. Nancy and Joe flew back at 6 a.m. 

The MLS is on break now for the FIFA World Cup. Charlotte’s next game is July 27. Will had a short break but is back working with Crown Legacy FC, the reserve team of Charlotte FC. “I want to keep working, keep pushing, so when the season starts, I’ll be good to go.” 

At the moment, the soccer world — and many who generally don’t pay attention to the game — is caught up in the World Cup, an event that comes around every four years. There are 48 teams in this year’s tournament, the most in the history of the event, and games are being contested in Canada, Mexico, and the United States. The World Cup began on June 11 and continues through July 19. FIFA, which is the governing body of the sport, estimated 6 billion people will watch games in some form. 

Will said the only thing he can think of that comes close to the global appeal of the World Cup is the Olympics. “Every soccer player dreams of representing their country and being on that stage. It really is the biggest stage in sports. I don’t think there's much like it.”   

He said what he enjoys most about playing soccer is the team aspect. “There is individual brilliance,” he said, “but at the end of the day if you are not surrounded by people working as hard as you are, you have no chance at succeeding, so it’s about the group. How you fit into the group and how you can make that group the best it possibly can be. And that will change because the starting lineup changes and you’re filling a different role. There are tweaks you have to make.” 

Will has had to tweak his game. He is a defender in the MLS, the position he played at Stanford. At Loomis Chaffee he was a center midfielder.  

“Another thing I loved about being at Loomis was I wasn’t limited to just playing soccer,” Will said. “I could compete across all three seasons, and I think that helped me in soccer when I went to Stanford and switched positions, becoming a defender. It was similar to defending in basketball, so I didn’t have much trouble getting used to that.” 

Will also enjoyed the social aspect outside of sports at Loomis and the tight-knit community. “I made great friends and met people from around the world,” he said, “and that has helped me connect to my teammates now, who are from all over the world and from all different walks of life. Being exposed to so many others at Loomis was a blessing.”