Craig Stewart is dedicated to educational excellence and helping people achieve their personal best. That's the thread that connects a career that has stretched in several directions—from soldier, to CIA officer, to college dean, to development director at Lakeside School, to trustee and president of Bruce '64 and Jolene McCaw's philanthropic foundation.

After graduating from Middlebury College in 1963, where he went through a Reserve Officers' Training Corps Program (ROTC), he joined the Army as a second lieutenant, spending three years on active duty, including in Korea. He did graduate work in law and public policy, then entered a career training program to become a case officer for the CIA. His work at the agency focused on Southeast Asia, a hot spot in the late 1960s.

He became an employee relations manager with Standard Oil of Ohio and later vice president of university relations at Lewis University, while earning an MA in ethnic studies and a doctorate in higher education. In 1976, Bruce Bailey '59, a fellow Middlebury classmate, told him Lakeside was looking for an athletic director and a physical education teacher. Athletics was a major passion for Stewart and when he and his wife, Val, met Dan Ayrault, then head of Lakeside, they felt an immediate connection.

"The next three years were a whirlwind," Stewart recalls. "Lakeside changed the athletic league we were playing in from single A competing with teams throughout the state to Seattle AA Metro—a move that allowed us to compete locally against schools with substantially more racial and ethnic diversity, which we valued. In addition to a new library and performing arts center the school raised money for a new field house. I also served as director of Lakeside Educational Enrichment Program (LEEP) for two summers. Val taught physical education. Our son Clint was born. The teachers were as talented as they are today. The students were highly motivated. It was an exceptional period of time for our family and the world."

To be closer to family Stewart headed East for a time to work at other schools but Lakeside pulled him back to become development director in 1986. "It was a wonderful 10-year run marred by Dan's untimely and tragic death in 1990. We had an amazing Board and development committee; the alumni and parent volunteer leadership were enthusiastic. I had a development team that was awesome! And both my kids were attending Lakeside."

"During the capital campaign at the time, several trustees, faculty, and some alumni shared with us their commitment to include the school in their estate plans," Stewart says. "This seemed an opportune time to launch the Founders Circle and to honor those individuals and families committed to Lakeside's future. The Board did so in 1993; it was the beginning of the school's planned giving program.

"I was pleased to join the Founders Circle by naming Lakeside as a beneficiary of a current life insurance policy held in my name, a simple thing to do. I since have decided to include Lakeside in my will and have designated this bequest go to the Dan Ayrault LEEP Endowment."

After 10 years of success at Lakeside, Stewart received an offer he couldn't refuse from a mentor and friend. Bruce McCaw '64 and his wife Jolene asked Stewart to oversee their philanthropic interests. "It has been quite a ride," Stewart says. "A centerpiece of our grant-making has been education, which resulted in the creation of Talaris Institute, whose mission is to support parents and caregivers in raising socially and emotionally healthy children. Many organizations in the Northwest, nationally, and internationally have been the beneficiaries of Bruce's and Jolene's generosity."

Stewart has dedicated his life to helping others reach their full potential. "My wish would be that everyone could have the same opportunities and access that I've had," he says. "That's why Lakeside School is so special. I feel deeply indebted to the teachers and coaches and all they have given our family."