McCulloch retires June 30 after 37 years in education, the last seven at Los Gatos High School. The Oakland native started out teaching mathematics at Piedmont Hills High School in San Jose, and then spent 12 years as a counselor at Piedmont Hills and Independence high schools. She's also served as vice principal and principal at Mt. Pleasant High School in the East Side Union High School District, and still lives on the east side of San Jose.

"When I was a teacher I said I'd never leave the classroom, and then counseling appealed to me because you saw the students in a different light," she said.

When she was a counselor, McCulloch thought she'd never leave counseling, and then she became an administrator.

"You can't believe anything I say," McCulloch said, laughing. "I see things and I say, 'I could do that.' I never disliked what I was doing, it was just something different."

McCulloch assumed the Los Gatos principal post when longtime principal and educator Ted Simonson retired.

"She's been wonderful not just as a boss, but as a friend," said Pat MacKay, McCulloch's secretary of seven years. "I work alongside her, not for her." MacKay credited McCulloch with making tremendous improvements to the school, its programs and its staff--all aspects that McCulloch's successor, assistant Principal Doug Ramezane, plans to continue.

"You can bring something to Trudy and discuss it with her, and she'll let you know if something can be done about it. It's been a real pleasure to work with her," said Tina Orsi-Hartigan, a new parent in the Los Gatos-Saratoga Joint Union High School District and Los Gatos Union School District board member.

James MacKay, Pat's son, who will enter his junior year in the fall, said McCulloch has raised the bar of educational standards at the school. She's also helped to lead the student population through the deaths of three of classmates--Eric Quesada, Megan O'Donnell and most recently Bryce Byrd.

"It's a relationship where we both acknowledge each other by saying hello, and she checks up on me and treats everyone equally. She makes sure students get help when they need it," James said.

Assistant Principal Dan Fowler used a sports analogy to explain that McCulloch lets the people who work for her play the game and do it the way they do best. But she's also there for them if they need a little coaching. Fowler said McCulloch has a desire to make the Los Gatos High campus safe and comfortable.

Fowler also said McCulloch's legacy will be the "Alive ... and Loving Life" program, which promotes safe alternatives to drinking and driving for teenagers. The program is a way to reach out to all students.

"I did announce at my last 'Alive ... and Loving Life' meeting that I will stay involved," she confirmed.

In her retirement, other than having fun, McCulloch hopes to mentor new teachers and possibly teach in the administrative education program at San José State University.

McCulloch also brought Turnaround Scholarships to the school district, with the help of the Los Gatos Kiwanis. The scholarships assist students who might not otherwise be recognized for their efforts.

"We're all going to miss her," Fowler said. "We're really fortunate Doug has worked with her for so long, and I think we're going to thrive under his leadership." Ramezane and assistant Principal Kathleen Eaton came on board when McCulloch started at Los Gatos High, so they've worked together seven years.

"The thing I'll miss most about Trudy is she's just a caring and loving person. She's sharp," Ramezane said. "I'll miss her spirit and warmth."

McCulloch has helped to broaden course offerings at the school that appeal to more students.

"My passion, one of them, is that every single person on this campus is treated like an individual with respect and dignity. I think we've made great inroads with that," she said.

She has helped to implement a diversity task force, international fair, challenge days, Camp Anytown leadership conference, the Link Crew freshman transition program, and many other opportunities that empower students. She's also overseen the school as it's undergone the Measure B bond renovation, which is nearing completion.

"We're almost there," she said. "I think I can confidently say the kids and the staff will have the buildings they deserve."