She was the 1970 Kamehameha Schools graduate who was hired to breathe new life into an organization tarnished by ethics controversies and legal challenges.
But as Dee Jay Mailer announced her retirement today, the trust is now serving more Hawaiians than ever and has the financial strength to do so.
"She's done an outstanding job, absolutely outstanding," said Beadie Kanahele Dawson, former spokeswoman for the parent, alumni group Na Pua a Ke Alii Pauahi.
"She instilled a new confidence in the school, on the part of the community, on the part of alums, on the part of faculty."
During her tenure, Kamehameha Schools has grown from serving about 35,000 native Hawaiians students and adults to over 47,000 while its endowment has grown from $6 billion dollars to over $9 billion.
The growth was especially felt on the neighbor islands.
"We had not completed the Maui campus and the Keaau campus. Those were completed in her time and we're now in the fifth or sixth graduating classes," said Douglas Ing, former Kamehameha Schools trustee.
"Intelligence, good sense of judgement, character, integrity, humility, Dee Jay all of those characteristics and qualities and that's what made her a good leader."
Mailer's appointment came at a difficult transition period. The trust's tax exempt status had been at risk recently and its admissions policy was being challenged in the courts."
"There were so many almost incestuous relationships amongst the previous people at Kamehameha, it was necessary to have a new confidence built around someone who had nothing to do with the controversy," said Dawson.
Mailer earned nearly $600,000 as CEO. The Kamehameha Schools says it will conduct a global search for her successor.