Saint Louis School was on the verge of closing its doors on a long, storied history when Kauai-born Glenn Medeiros, a pop singer-­turned-educator, was hired in July 2015 as head of school to turn around the private institution’s fortunes.

The all-boys Catholic school was $10 million in debt, and administrators were concerned about whether they could make the next payroll. Enrollment was declining, as were endowments.

Medeiros, who came from positions at Maryknoll School and Chaminade University, huddled with a couple of Saint Louis trustees after being brought on board to develop a strategy to restore the nonprofit school to prosperity. One of the first steps Medeiros took in conjunction with the board was cutting a half­-million dollars in expenses his first year to stem the bleeding.

About 10 positions were eliminated from the roughly 90-person staff during Medeiros’ first month at the helm. Then two years later, maintenance, classroom cleaning, landscaping and human resources positions were outsourced, resulting in the loss of about 20 additional workers, many of whom had been there for almost 20 years. After that, in preparation for the pandemic, nine more employees were let go.

To boost enrollment, Medeiros approved adding a fifth grade to the school’s sixth through 12th grade. The following school year, as the newly named president at Saint Louis, Medeiros added kindergarten through fourth grade.

Now in the eighth year under his oversight, the 176-year-old school has boosted its enrollment more than 50% from the mid-500s — prior to adding fifth grade — to about 860 today, doubled its endowments and reduced its debt to about $3 million, with the balance scheduled to be paid off in about 18 months.

“We are in good financial shape now,” said the 52-year-old Medeiros, who achieved global music fame in the late 1980s and early ’90s with hit songs like “Nothing’s Gonna Change My Love for You” and “She Ain’t Worth It.”

“We still have some ways to go to be where we want to be, but we’re quite healthy right now. And I must say thank you to our faculty, staff and administrators that have worked so hard. But, in particular, at Saint Louis School, the alumni are fantastic.”

During his tenure, the school raised funds needed for classrooms, educational programs and office space while building the new Clarence T.C. Ching Athletic Center. Saint Louis’ debt, which had dropped to below $1 million, increased to about $3 million because of the athletic center, but Medeiros said the school has pledges to pay off the athletic center and expects the school’s entire debt to be wiped out by the middle of 2024.

In addition, Medeiros improved employee benefits to provide discounts to families with multiple children, as well as grandchildren, attending Saint Louis School, which has a tuition of $15,100 for elementary school, $16,630 for middle school and $18,700 for high school.

While Medeiros’ moves have paid off financially, eliminating positions, outsourcing and other cuts didn’t make him the most popular man on campus among those affected.

“It’s very difficult to let people go from their jobs,” he said. “It’s their livelihood. The hard part for me as president, I need to be able to look out for the school, also. And in my position I have to make the tough decisions. By making the moves that I did, I ultimately helped save the jobs of others that had been at the school, because it could have gone the other way (and the school could have closed).”

An undercurrent of discontent and upheaval has persisted, however.

Saint Louis’ chief financial officer, principal, athletic director and dean of students for the lower school were among those who resigned, as did a couple of trustees, citing Medeiros’ decisions, management style or both.

There were two formal complaints about Medeiros that the board investigated, and consultants were hired by the board to advise him on handling employees. Medeiros said those consultants have helped him deal with some management issues.

Dr. Arnold Kop, a Saint Louis alumnus who resigned from the school’s board of trustees in September, said he stepped down because he felt the board wasn’t holding Medeiros accountable for his actions as a leader.

“Despite the investigations, I didn’t feel there was much change in terms of where I saw the school going,” Kop said. “I think he should resign because he has run the school in an underlying toxic environment.

“He has been supported by the majority of the board of trustees, and I believe many of them haven’t done their fiduciary duty to oversee the deficiencies of the president of the school. How he treats people repeatedly is not very Christian.”

Kevin Chong Kee, a board member and president of the Saint Louis Alumni Association, said he is concerned about complaints the school has received and that the school needs to “hash it out” with all the parties involved.

“His management style is different,” Chong Kee said. “Because of the number of resignations, it comes into question. If you’re laying off your workers or people are resigning, you need to find out what the problem is and have an open discussion about what’s going on.”

Saint Louis School Board of Trustees Chair David Coleman said when Medeiros was hired, he was brought in as a visionary to turn around the school’s dire financial situation. Coleman acknowledged that there was discontent with some of Medeiros’ moves but said that following an internal investigation, the board gave him a 24-0 vote of confidence in June.

“He had to make some pretty hard decisions, and some of that discontent that we had to deal with to some degree is coming from those changes,” said Coleman.

Coleman said there were two formal complaints that the board investigated and some informal ones.

“We took those complaints very seriously and engaged an internal but independent investigator,” he said. “We brought in an investigative lawyer who spent about six months in a process of interviewing and recording and working with the trustees. Following the findings of the investigator, the board of trustees and the president worked out a new leadership structure that would enhance and clarify collaborative decision­-making for senior and middle-level management. We believe the causes of discontent had to do with the ability and clarity of communication. That new structure we’re in the process of implementing. We’ve seen positive results for the leadership team. From our point of view, those particular issues are closed.”

Coleman also takes issue with the toxic-workplace characterization. “I would clearly disagree with the description of the work environment as being toxic, certainly in the way we use that term,” he said.

Saint Louis head football coach Ron Lee said the school’s culture has turned around since he and his brother, Cal, came back to the school in 2014.

“We had a lot of kids that were on probation academically, really struggling, and the school was really in bad shape financially and the enrollment not going in the right direction,” Lee said. “When I see the change from 2014 since Glenn Medeiros has come on board, the attitude, the culture of the school and the kids, it’s a tremendous difference. We don’t have anyone on probation like it was eight, nine years ago.”

Retired First Hawaiian Bank CEO Walter Dods, who graduated in the Saint Louis class of 1959 and is a former chair of the trustees, acknowledged the school was on the verge of collapse when Medeiros took over.

“The school was in trouble,” he said. “It had gotten pretty close to the number (of students) where it couldn’t sustain itself. He’s done a dramatic job.”

Dods said people really don’t understand how Saint Louis compares with the other high-profile private schools.

“We compare Saint Louis with Punahou and ‘Iolani, but Saint Louis historically is a blue-collar school,” he said. “We hadn’t raised a lot of money, but in recent years under Glenn’s watch, we started raising money again. Within the last six months we raised $3 million, which seems like peanuts for Punahou and ‘Iolani. But that’s $2.5 million more than they’ve ever raised. From my point of view, he’s really rejuvenated the school.”

P. Gregory Frey, who preceded Chong Kee as president of the Saint Louis Alumni Association and is a trustee emeritus, was on the selection committee that chose Medeiros and said he has never seen anyone as passionate as him.

Medeiros, who said he became a teacher because he wanted students to believe in themselves, began his education career in 1994 and capped it off with a doctorate in educational leadership from the University of Southern California in 2014.

“I’ve never seen him do anything but be thoughtful, professional, dedicated, devoted to protocol and amazingly in tune with the positions of everybody in the room, even if they are diverse and divergent,” Frey said.