Assistant football coach gets promoted — to hoops

January 23, 2026
3 mins read
Boys’ basketball coach Jeff Brewington talks to his team during a timeout at a recent game. (Photo by Brad Spiegel)

By Brad Spiegel
brad.spiegel@waylandpost.org


He’s back — but it seems like he never really left.
That’s because Jeff Brewington, the former Wayland High School basketball great, has been roaming his old high school for 10 years as an assistant football coach. But now Brewington, 33, has taken the reins for the basketball program as its head man, replacing longtime coach Dennis Doherty.
“It’s been surreal,” said Brewington. “I know the job Dennis did. And I know the big shoes I have to fill. The job definitely comes with gravity to it that I make sure the program is in good hands, and I take the role seriously.”
Brewington, who grew up in Dorchester, was a METCO student in Wayland schools beginning in first grade. His basketball playing days started in seventh grade under coach Kevin Farley, who is now on his coaching staff.
He was a call-up for the MIAA tournament as a freshman in the 2006-07 season. That was followed by “decent success” as a sophomore and junior before the team excelled in his senior year when the Warriors went 16-6 and advanced through the first two rounds of the tournament.
Brewington decided to play football at Williams College. That’s the sport where he has attained most of his coaching experience – two years in Oklahoma City and one at Lincoln-Sudbury (where he is a math teacher) before Wayland. But the lure of being the head basketball coach at his alma mater was one he couldn’t pass up.
“When I heard the job was opening, I knew there would be a bit of a learning curve on the basketball side. But I’ve been coaching one way or another for some time. I was willing to do the prep work to put the team in the right spot,” Brewington said.
​If early results are any indication, it’s safe to say Brewington and the Warriors are on the right path. Through the first half of the season, Wayland stands at 5-5. That’s a stark contrast to the previous four seasons that saw a combined 16-41 mark.There was an especially satisfying victory recently when the Warriors avenged a 20-point loss to their rival, Weston, with a three-point victory just one week later.
​“I would say we are a bit ahead of schedule,” Brewington said. “And two of those losses — Cathedral and Bellingham — were against good teams. And we only lost by two points to each.”
Of course, Brewington isn’t taking the credit. He and his coaching staff, which features another familiar face in Jonathan Eng (Class of 2016), have high expectations for the team.
“We’re pushing them and they have stepped up with, honestly, not many questions asked,” he said. “I think we’re in a very good spot. We’re riding decent early-season momentum, and if we stay focused, we should continue our upward trajectory.”
Athletic Director Heath Rollins is a strong advocate for bringing back players. He boasts many hires of former Warriors, so bringing on Brewington was not a difficult decision.
“Jeff’s been around [WHS] for 10 years, so I knew what a great person and coach he is,” Rollins said. “Having someone like Jeff, someone who has been in [current students’] shoes, is great to have. He knows the students, he’s been in the system, and knows the expectations.”
But there’s an added bonus: the effect it has on the players. It gives them someone they can look up to and emulate because their coaches have been through what they are experiencing.
“Former players who come back to coach show a passion for the sport,” Rollins explained. “It’s someone who has been through it and wanted to come back because it was such a good experience when they were here as a student.”
Brewington inherited a balanced team with four returning varsity players among the five seniors, five juniors, and three sophomores. Since the start of the season, a senior (unhappy with his playing time) and a junior (focusing on another sport) have left the program.
Brewington added that the state in which Dennis Doherty, his coach as a junior and senior, left the program, despite the team’s record, made his first couple of months much easier.
“I have to give a nod to Dennis Doherty; I learned so much from him and appreciate the foundation he laid,” Brewington said. “Being tangentially aware of what he did for the program when I played for him, and seeing it through other kids who played for him, I can’t thank him enough. It’s helped me hit the ground running.”

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