In 1991, Jason O’Donnell was on Coach Donald Herman’s first state championship football team at the Martha’s Vineyard Regional High School.

On Monday, Mr. O’Donnell is out on the field with the four other varsity assistant coaches alongside Coach Herman, helping the team prepare for the Island Cup this weekend.

“Working with kids is something I’ve always enjoyed doing, and I wanted to give back to the program that has given me so much,” said Mr. O’Donnell. “Donald definitely changed this program around to what it is right now.”

Neil Estrella, an assistant coach who also played in the 1991 state championship game, agrees.

“There was a bunch of individuals before Coach Herman came,” he said. “Everybody was an individual athlete all about themselves. But he said, ‘No, that’s not the way it’s supposed to be.’”

Mr. O’Donnell added: “He brought us together as a family. That’s just how I’ve always envisioned a coach should be, and how I've always wanted to be.”

All five coaches, whether they played at the high school or not, attribute the camaraderie of a football team as the reason why they decided to coach.

Tom Keller is coaching for his first year at Martha’s Vineyard, but has been coaching at both the high school and college level for 33 years.

“After I finished college I looked at what the most poignant moments of my life had been and almost every one of them happened as part of a team,” he said. “And the people I had special connections with were my coaches. For some it might be a math or science teacher, but for me, it was always a coach that had a big influence on me.”

He said the challenge of coaching lies within balancing the intense emotions of the players with the delicate structure and swift execution of the plays.

“It’s a very primal game, going back to the roots of our existence,” he said. “Like two cavemen fighting for a piece of meat. But you also have to run the routes correctly. There is a lot of finesse to it at the same time.”

David Araujo, who played at the high school and has been coaching for four years, said handling the boys’ emotions requires a particular art.

“Some days you are strict and tough, other days you have to coddle them,” he said. “You have to know your kids and be able to look them in the eyes and figure out what the best approach and treatment is for each kid.”

Sterling Bishop, who is coaching football for the first time this year, said being part of a team helped him adjust to high school.

“It’s tough coming to high school and having to fit in socially,” he said. “If you have a full team behind you, it makes that transition much easier.”

He said when he was playing football in school, he used sports as an incentive to do well academically.

“I used my athleticism to motivate me to keep my grades up, so I want to give that message to the kids,” said Mr. Bishop.

Mr. Estrella agreed that playing on the team gave him the focus he needed as a teenager.

“It kept us out of trouble,” he laughed. “We didn’t have the teen center or the YMCA or all that other stuff. It was the only thing that gave us something constructive to do.”

Mr. Estrella said that despite the key injuries the team suffered this season, the guys were still able to play with resilience and fluidity.

Mr. Keller said the game against Bishop Stang in the beginning of November is when he saw the team’s efforts really pay off.

“We had a play where we had a yard to make, and we had a quarterback sneak,” he said. “For the first time, I saw 11 guys come together. For a brief instance, we weren’t a whole lot different from the New England Patriots.”

Mr. Araujo said the heat will be turned on for the Island Cup this weekend, with jam-packed bleachers watching a rivalry at its best.

“It’s like a civil war,” Mr. Araujo said of the annual game between Nantucket and Martha’s Vineyard. “You are playing people so similar to us; they’re an island; they live the same lifestyle as us. It’s almost like playing your brother, except you don’t like your brother one bit.”

Mr. Keller added: “You could be 0 and whatever, and if you win your last game, it’s a successful year. Or you could be 8 and 0 and lose that game. It’s like you lost everything . . . There’s nothing like football game day.”