Nantucket caddying helps Wellesley student land coveted college scholarship
Wellesley’s Tawanda Masiiwa would not have earned the Chick Evans Scholarship—which covers $125,000 in college tuition and housing expenses—if not for encouragement from his seventh grade football coach to apply for a summer caddie camp at Sankaty Head Golf Club in Nantucket. His coach knew about the program because he was a neighbor of the camp’s director, Dave Hinman.
“So, I sent in the application, and then Mr. Hinman set up an interview for me over Zoom. After that Zoom call, I think two days later, I got an acceptance letter,” Masiiwa recalled.
Masiiwa’s route to the Western Golf Association’s Evans Scholarship actually started at the height of the COVID-19 pandemic, when golf courses were among the businesses still able to operate somewhat normally. Facing the potential for a summer stuck inside after finishing 7th grade at Belmont Hill School and wanting to try something new, Masiiwa reached out to caddie master Tony Gomes at Newton’s Brae Burn Country Club to inquire about a caddying opportunity. Although he had never caddied or played much golf, Masiiwa got the job, first training and then starting as a caddy in 8th grade .
Fast forward to Masiiwa’s arrival on Nantucket the summer after his freshman year in high school, and Hinman could see he had a fast learner in the young man despite his limited caddying and golf experience.
“Our first-year caddies have a lot to learn when they arrive. Tawanda had a little background in golf so he picked things up pretty quickly,” Hinman observed. “We do an extensive training program that is led by our most senior, experienced caddies.”
Masiiwa had enough experience to adapt quickly. During eighth grade, he’d wake up at 6:00 a.m. every day, and he would frequently bike over to the Brae Burn course if his dad could not drive him. Masiiwa would also caddy on Sundays if he did not have church.
Masiiwa credits his parents for encouraging him to pursue all four years of the Sankaty Head Caddie Program and sending him to great schools throughout his childhood like Tenacre Country Day School and Belmont Hill. He felt that they deserved something in return.
“[Caddying] is a great opportunity to make money, meet some friends and just have a new experience in total,” Masiiwa said.
“Every time I come back, I love it,” he said. “Every time I meet someone new, it’s always great. Everyone is always nice, and I’m close with them, which is great.”
His days on the island were demanding. Masiiwa woke at 7:00 a.m. each day throughout the summer and 20 minutes later, he was dressed in uniform and ready to go. He said it was similar to his days caddying at Brae Burn, but also like overnight camp.
The commitment made it all worth it for Masiiwa. In December 2024, he’d been receiving admission letters from colleges, but one day he received a different type of correspondence: Notification that he was a recipient of the Evans Scholarship, a program established in 1930 and that currently supports nearly 1,200 students at colleges across the country. Masiiwa plans to study economics at Miami University in Ohio.
To qualify for the scholarship, students had to meet selection criteria that included showing a strong caddie record, excellent academics, financial need, and outstanding character.
Sankaty Head Caddie Program’s Hinman has been high on Masiiwa’s capabilities from the start. “I receive feedback from golfers every day, and over the years, Tawanda’s record has been perfect,” he shared.
“Our goal is not for Tawanda to be a caddie. Our program’s mission is to help youth be successful in college and beyond,” Hinman explained. “Caddying teaches youth how to interact with people and to value hard work and perseverance. Our residential program teaches independence and how to live with others.”
Writer Jason Glick is a rising sophomore at the S.I. Newhouse School of Public Communications at Syracuse University in the Broadcast and Digital Journalism major.
More from Jason Glick: Wellesley’s Gopal takes his academic and baseball talents to the U.S. Naval Academy