Peer behind Diamond Head Theatre’s grand burgundy curtain, and you’ll see a new wizard is in town. Local boy Trevor Tamashiro has been named the new executive director of Hawai‘i’s oldest theater, following Deena Dray’s retirement after a nearly three-decade run. 

Tamashiro comes to the theater, which is affectionately called the “Broadway of the Pacific,” from the real Broadway in New York City, where he performed on stage until a career-altering injury. Unwilling to give a final bow to the art world, Tamashiro moved out of the spotlight and behind the scenes to work in the administrative sector. He held positions at The Diller-Quaile School of Music, Saratoga International Theater Institute and The Drama League of New York, where he got to see more than 100 productions a year in preparation for the company’s award show, which is a prerequisite for the Tony Awards.

“That really allowed me to learn as much as I could about the industry and theater from small-scale productions to major Broadway productions, and just to see a range of work,” says Tamashiro, a graduate of Colombia University.

Following a vivacious 20-something years in the theater capital of America, Tamashiro clicked his metaphorical ruby heels three times, ready to come home. 

Born and raised in the islands, the Punahou School alum grew up in ‘Aiea and was an active member of the local community theater scene from the late ’90s to 2000s. He acted, sang and danced in high school performances and on the stages of Kumu Kahua Theatre, the now-closed Richardson Theater at Fort Shafter and, charmingly, Diamond Head Theatre. 

“I discovered a love for the theater at a young age,” says Tamashiro. “I remember feeling scared and excited at the same time; there’s an exhilaration of being on stage that’s addicting. I think from that, as they say, I caught the bug.”

During his first week back at Diamond Head Theatre, the costume crew discovered attire worn by Tamashiro in the 1997 production of King & I, embroidered with his name and all. He calls this nostalgic happenstance “random,” but some may say it’s a good omen.

“It feels surreal being back. I sometimes can’t believe this is really happening,” he says. “I feel really blessed to be able to return to my roots; to come back to a community and a theater that has given so much to me. It’s truly an honor to be able to now give back to this community, to be able to create transpersonal experiences and connections for audiences, and to support and nurture future generations of artists here in Hawai‘i.” 

It’s a new dawn for Diamond Head Theatre, which was established in 1915, making it the nation’s third oldest, continuously operating theater. Not only does it have a shiny new executive director, but its historic Makapu‘u Avenue playhouse was recently scrapped and (mostly) rebuilt in 2022. The nonprofit introduced a state-of-the-art 17,000-square-foot theater to audiences at the beginning of the year. 

At the time of the interview, Tamashiro was only six weeks into the gig, still learning the choreography and how to lead the troupe. And while he’s not ready to reveal his vision quite yet, he did share where his passion thrives the most. 

“Expanding arts education programs is going to be really important to me, and how we break barriers and engage as much youth as possible into our programs,” says Tamashiro. “I want to break down socioeconomic backgrounds, making sure everybody has the ability to participate in our programs.” 

On top of its seasonal shows — which, this year, include Mamma Mia (Sept. 22- Oct. 8), My Fair Lady (Dec. 1-17) and The Musical Comedy Murders of 1940 (Feb. 2-18) — the nonprofit also offers year-round classes, during which community members of all ages, backgrounds and levels can learn how to act, dance and sing in small groups. 

“For me, the theater is a social space,” says Tamashiro. “It can be a source of expression for people that may not have that. I found this community, this theater ‘ohana in Hawai‘i, that really nurtured me and made me feel safe, and gave me a place where I was able to flourish and be creative, so I think continuing that is really important.” 

While Tamashiro continues to explore his new role, and master the dance of legacy and innovation, his heart is set on the community that built him, and to provide them with live entertainment they’ll not soon forget. 

As they say, there’s no place like home. 

“Good theater entertains. Great theater changes lives. I love that the theater can be a transformative experience for people. Not only can it allow you to escape the reality of the real world for a moment, but it can also make you feel happy, it can make you think, it can make you innovate, and it can make you dream,” says Tamashiro. “I think that’s the true magic of theater.”