New Beginnings

By early 2002, the board realized that the August 2002 opening was not feasible and postponed it another two years. The board also approved plans to “soft launch” the school with middle school grades only.

The early years were consumed with securing a location and raising funds for construction. While many individuals stepped forward with donations, the board worked tirelessly to secure large grants from foundations. Maui councilwoman Joanne Johnson introduced a special resolution to accelerate the permitting process, and ten local realtors established AIM (Alliance to Improve Maui) with a goal of raising $1.5 million. The board continued to affirm the Fall 2005 opening with provisional classroom plans should the campus not be established yet.

In June 2003, the board struck a deal with Maui Land & Pineapple Co to purchase the Honolua Dormitory Complex site. They engaged an attorney to draft an agreement, and hired an architect, consultants, and other engineers to draft a master plan and conduct required site studies. For the first time, the idea of Maui Prep had a home. In 2004, MLP committed to donate nearly 21 acres to the school (the final deed transfer occurred in 2011), and stakeholders signed on as personal guarantors for the $4.2 million construction loan. Independent schools, especially brand new ones, do not receive government funds, so the capital required to renovate and furnish the old dormitories into safe and comfortable classrooms had to come through grants and fundraising. Tom Rosenquist was an early advocate for the school and served as the Board of Trustees president. A successful truck driver turned land developer and philanthropist, Mr Rosenquist helped secure a loan that would allow Maui Prep to renovate the buildings. With the campus design plan complete, the work was put out for bid, with an anticipated 120 day construction time. However, as the September 6, 2005 opening date loomed, the campus was still a construction zone.

Founding faculty member Ms Shannon Cleary (2005-2007) heard whispers that a new school in Napili was forming, and applied for the Assistant to the Head of School position. After her interview with original head of school John Colson, she exited the room as the Foreign Language Chair, Japanese teacher, and Admissions Director. The interview process also included a tutorial in the correct pronunciation of “preparatory,” recalls Ms Cleary. Ms Leigh Fitzgerald (2005- 2010) added that it was pronounced “Maui ‘PRE-para-tory’ because we were preparing kids for college.” Despite the name, the educators knew that “Preparatory” meant more than just producing college-ready students. Ms Fitz, as students will remember her, identified that it was her duty to “to prepare students for life after [Maui Prep]: be it college, travel, career, internship, community college, or a semi-pro athletic career.”

The Kapalua Bay Hotel general manager offered the hotel’s ballrooms as makeshift classrooms until the construction was complete. Current college counselor and upper school teacher Mr Keenan Reader (2005 to present) joined the Maui Prep faculty as a math teacher for the inaugural year. “Lunches at the Kapalua Bay were epic!” he reminisced. “We ate in the employee lunch room and had access to a soft-serve ice cream machine.” The students took breaks on the green lawn that stretched between the now-demolished hotel and world-class Kapalua Bay. Reader jokes that he and “a much younger” Mr [Ryan] Kirkham (2005 to present) would punt footballs and watch as kids collided and the balls bounced off their heads.” When the hotel required their spaces for guest purposes, the administration scrambled to organize impromptu field trips. Quick on their feet, the faculty once rented vans and transported the students to the Kepaniwai Park Heritage Garden Park in ‘Iao Valley. The hotel stay was brief, only 6 weeks. On October 17, 2005, now known as Founders’ Day, the entire operation moved into its permanent home.

Pulling double duty as administrator and teacher meant that Ms Cleary shuttled back and forth between the hotel and the Napili campus several times each day. The road that connects the campus to Napilihau Street had not yet been paved so the administration traipsed up and down the red-clad dirt, and, more often than not, muddy hills. Cleary recalls, “We had one office that we shared where we also hosted Board meetings. Ryan [Kirkham] ordered more science stuff than any one school could imagine – taking up one-third of the office.”

Ms Fitzgerald joined the faculty during the transition from the hotel to the campus. The perpetual construction zone allowed the school to be built around the students’ needs. “The first year was so FUN! Everyday was the community coming together to both figure out our program, our space, and our mission/vision for the students and the campus,” Ms Fitz commented. “It was true ‘ohana- everyone was in it together.” It seems that everyone was filling multiple roles. “The many hats worn were the challenge and the joy.”

Faculty, parents and students rolled up their sleeves, hanging whiteboards and smartboards in each classroom, feeding internet cable, or assembling desks and furniture. Rosenquist made weekly visits to the campus reminding everyone, “It’s for the kids!” Maui Prep also received its first foundation grants– from the First Hawaiian Bank Foundation and the Cooke Foundation, both who continue to support Maui Prep to this day.

Middle school rites of passage were not overlooked as the students returned to the Kapalua Bay Hotel for a Halloween dance, then transformed the dining hall into a dance floor for Valentines Day. Word about the new school on Napili was getting around and enrollment soon doubled. Maui Prep intended to expand to a high school program by adding one grade at a time, but in October 2005, a group of elementary school-aged parents asked the Board of Trustees to include kindergarten through 5th grade classes.

The small student body and faculty and staff allowed lasting relationships to be formed. “In the beginning, the students seemed to love and thrive in the small environment,” Ms Cleary reminisced, “I can think of one or two who wished to ‘disappear’ a bit more, which was impossible with a school of that size. Many are still very close today.” Ms Fitzgerald recounts that, “The students were like siblings- everyone had a unique quality that was appreciated by every other student. They were all pioneers. It was also very casual at times because we were all together so much.”

The solid relationships within the Maui Prep community became paramount when Ms Cleary’s younger brother, First Lieutenant Michael J Cleary, was killed in an ambush in Iraq the week before Christmas and ten days prior to the end of his tour. “The entire community cared for me from afar,” Ms Cleary recalls.

In addition to the core classes of math, English/language arts, science, and history, Maui Prep quickly laid the foundation of its Performing Arts Department, and staged the school’s first musical: You’re a Good Man, Charlie Brown. Dr Rizzo recruited a former student, Chris Webb, to direct the show in the spring of 2006. The faculty sprang into action, giving support to choreography, costumes, set design and construction, and props. The sets were assembled from lumber scavenged from the trash and a team of students provided marketing and ran lighting and sound for the show. Ms Fitzgerald, a self-proclaimed “non-seamstress” was assigned to create costumes with several students. Ever resourceful, they “literally went shopping and then glue-gunned everything together because we had no idea what we were doing.” Director Webb fell ill in the last weeks of rehearsals and newly hired music teacher Mrs Vania Jerome (2005 to 2024) took over with the assistance of Pamela Chernick, a retired drama teacher. The number of eager student-thespians outnumbered the number of roles, so the show was double-cast with a performance for each ensemble at the Ritz- Carlton Kapalua Hotel. The students flocked to the extracurricular chorus and drama clubs, and a student council was elected.