Sean "Sonny" Fleming Scholarship

With a goal to be fully established in 2025 by fellow TCC caddies, the Sean “Sonny” Fleming Scholarship is in honor of a longtime beloved friend and caddie at The Country Club. For 41 years, Sonny made his presence felt with both the membership and his fellow caddies. Sonny was the undisputed leader and spirit of the caddie hut. Each day, Sonny put a smile on everyone’s face with his witty humor, but his most significant impact was being an exemplary role model for younger caddies and developing them into better people.

Over those four decades, a few lucky high school kids got to know Sonny every summer. Sonny would be the first one to make fun of them for having to wait hours in the caddie hut for a loop. After, if you were lucky enough to be paired up with him, you were not making it through 18 holes without laughing and learning. Many of those high school kids didn’t know it at the time, but Sonny instilled hard work and dedication into them daily. He helped them build character and hold a high standard of excellence. Sonny was the sole reason why many of them would come back year after year.

In honor of Sonny’s spirit and dedication, this endowed award is for a current Ouimet Scholar who caddied or still caddies at The Country Club and exemplifies the best of Sonny.

Triplets Chris and Dan Hughes grew up in West Roxbury and started caddying at TCC in 2011 when they were 14 years old. In 2016, the brothers were awarded Ouimet Scholarships - including the Anders Scholarship and the Newell, Pyle, Sears Scholarship, both endowed scholarships awarded to Ouimet Scholars from TCC - as they began their college career at Loyola University Maryland. Upon graduating after four years with a Bachelor’s Degree in Business Administration, they returned to Boston and joined the workforce. Today Chris lives in Dallas, TX, and is a manager at AT&T specializing in third-party partnerships. Dan lives locally and is a Sales Representative at Sentient Jet.

Inspired by the life lessons they learned while caddying and the mentorship provided by longtime TCC caddie Sean Fleming, Chris and Dan have been the driving force behind the creation of the Sean “Sonny” Fleming Endowed Scholarship. They have personally pledged funds and have successfully enlisted past and present TCC caddies, employees, and members to support their cause. By paying it forward and embracing the Ouimet motto of giving back, Chris and Dan have ensured that future generations of TCC caddies will have the same opportunities they did in addition to honoring their friend Sean Fleming’s legacy.