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Kevin O’Brien, shown working with student-athletes, has been a history teacher and the strength and conditioning coach at Kamehameha Schools Maui for the past 18 years. Previously, he was a teacher and football coach at St. Anthony. KAMEHAMEHA SCHOOLS MAUI photos
People Who Made a Difference: Sports Edition is a special series recognizing those in the Maui County sports community who have made significant impacts. Stories will run this summer in The Maui News.
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If there is one thing that students have learned from Kevin O’Brien, it’s how to be a go-getter.
As a longtime strength and conditioning coach and world history teacher at Kamehameha Schools Maui, O’Brien strives to help youth reach their potential by teaching them lessons and habits that will “benefit their whole life.”
“If you want to do something, go and do it– join that team, go on that trip, join that club, take that class,” he said on Monday morning. “Don’t close any doors. Be a doer. … That mindset will help you get better.”
O’Brien
The main mission as a coach is “trying to get somebody from where they are to where they can be, and to believe that they can get to where they don’t believe they can get to– intellectually, mentally, physically, emotionally,” he added. “Being a small part of helping kids do that is really gratifying.”
And his coaching philosophies don’t stop when he enters the classroom.
“I have tried to be a valuable member of the Maui community and have tried to just have good relationships with the young people and try to get them to the places where I know they can get to,” he said. “I love seeing somebody improve.”
O’Brien’s first job as a young man on Maui was in 1993 at St. Anthony High School, where he was a teacher and an assistant football coach under the tutelage of the late Charlie Ane and former athletics director Pat McCall.
He later became the Trojans’ head coach from 1999 through the 2003-04 season, a time that included the senior season of two-time World Series champion Shane Victorino. In 2017, Victorino discussed how O’Brien was “a major part of my life” in a video series by Sheraton Hotels & Resorts titled “Beyond Influential.”
Kevin O’Brien speaks with a Kamehameha Schools Maui student-athlete.
Eighteen years ago, Kamehameha Maui welcomed O’Brien as a history teacher and an essential figure in the athletics department. He has been the strength and conditioning coach for junior varsity and varsity teams — including football, volleyball, soccer, tennis and track — and was the head football coach from 2010-2012.
Briefly, he was also an assistant football coach at Seabury Hall from 2013-14.
“Coach Kevin is a huge asset on our campus, as a kumu and as a coach. His passion radiates through his ability to tap into student-athlete holistic development,” said Kamehameha Maui associate athletic director Mahina Hannemann-Gago. “We are blessed to have his presence on our campus and his positive impact on each of our haumana.”
Approaching the 30-year mark as a coach, teacher and mentor on Maui, O’Brien has undoubtedly made an impact on hundreds of students, coaches and coworkers islandwide.
“Looking back on my career, the best things may not necessarily be the X’s and O’s, it’s the relationships I’ve built with people,” he said. “I’m very, very fortunate with all the opportunities I’ve had, the relationships built.”
For Sofia Stupplebeen, a recently graduated Kamehameha soccer player, O’Brien was an influential mentor throughout her whole high school career with how he encouraged her to “be a doer.”
“I met him my freshman year and we were basically pals from the beginning all the way until the end, and he’s like that not with just me, but with all the kids– he just takes them under his wing and fosters them to become better athletes, better students, and just better in general,” Stupplebeen said. “It’s so great to have a teacher like that, who believes in you, supports you and wants the best for you, and that’s just who he is.”
A lot of student-athletes respect and look up to O’Brien, also known as “K.O.B.” on campus, for his ability to connect with each individual person and “treat us like we’re capable of more,” she added.
“He inspires me every day. Every time I walk into the weight room or the gym, he just tells me ‘Hey, you can do this’ and that ‘it’s going to be a challenge, but it’s nothing you can’t handle,’ “ said Stupplebeen, who plans to play soccer at the club level at Seattle University in the fall. “He’s just an awesome person. I’m sure if you ask any student who had him as a coach or teacher, they would say he’s an absolutely brilliant person and he’s just a wonderful part of your day.”
Drawing from his high school experiences as an “undersized football player,” O’Brien is a firm believer in weightlifting paired with having work ethic, attitude and self-motivation.
One of his proudest moments as a coach was assisting then-girls volleyball coach Alex Akana in getting the team prepared for what turned out to be a five-set victory in the 2017 Maui Interscholastic League championship match, he said.
Warriors football coach Ulima Afoa said that O’Brien is a positive influence for all girls and boys sports teams, inside and outside the classroom.
“He’s a charismatic leader with the kids, and gives them good advice about being a student-athlete and helps them overcome some of the challenges that they face academically,” Afoa said. “He’s been a big asset to this program.”
He added that “it’s amazing” the impact O’Brien makes on the players and how he manages to maintain strong bonds with the student-athletes even after they graduate high school.
But the road as a mentor hasn’t always been smooth for him. After being diagnosed with cancer in late 2019, O’Brien could not finish a football season for the first time in his life, which was “very difficult for me.”
“I’m one of those guys who never takes a sick day,” said O’Brien, who endured five operations and radiation to combat stage 4 melanoma, which was spreading rapidly from his scalp through his lymph nodes and neck.
By the end of March 2020, he entered remission and was ready to get back in the classroom and in the gym, but the COVID-19 pandemic hit and brought the academics and athletics world to a halt.
“Having cancer and then the COVID situation has been surreal,” he said. “I love going to school, I love being in the classroom, I love going into the weight room after school, I love football season, so that was hard for me.”
Despite the harsh realities of fighting and living with cancer, O’Brien said that “I’m so lucky and honored” for the life he has lived thus far and the people he has met along the way. And as the dust begins to settle, he is “stoked” for the coming fall season.
Though it’s not always easy, “I try to believe that there is a lesson to be learned no matter what.”
“Maui has been very good to me and St. Anthony has been very good to me and Kamehameha Schools Maui has been very good to me,” he said. “I just feel very fortunate that the Maui community has embraced me and I’m just super fortunate and very proud to be a part of it.”
* Dakota Grossman is at dgrossman@mauinews.com.
- Jill Biden
- Kevin O’Brien, shown working with student-athletes, has been a history teacher and the strength and conditioning coach at Kamehameha Schools Maui for the past 18 years. Previously, he was a teacher and football coach at St. Anthony. KAMEHAMEHA SCHOOLS MAUI photos
- Kevin O’Brien speaks with a Kamehameha Schools Maui student-athlete.
- O’Brien
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