An Independent School • Grades 5-12
Bruce Bailey ’59 receives Lakeside’s 2022-2023 Distinguished Alumni Award

Bruce Bailey ’59 was presented the Lakeside/St. Nicholas Distinguished Alumni Award at Upper School assembly on Nov. 2. Bailey was introduced by alumni board member Stephanie Saad ’94 Cuthbertson, who said, “Bruce Bailey was already a legend at the school when I was here as a student. …To Bruce, the word ‘alumni’ is a verb.” Bailey spoke movingly about how meaningful his long association with the school has been, especially being surrounded by such smart, motivated, and caring faculty and staff, and by such thoughtful and energetic students. He shared: “It never felt like going to work. It felt magical.” He shared a brief history of Lakeside and reflected on its evolution over the years, also acknowledging the 16 current alumni among Lakeside’s faculty and staff. Before fielding questions from students, Bailey closed with the following advice: “Whatever you end up doing, commit some of your energy and talents to the places that helped make you who you are. … Be good. Work hard. Vote, if you’re eligible. Go Lions.”

The following citation was read aloud as part of the presentation. 

Alumni board member Stephanie Saad ’94 Cuthbertson hands a framed award citation to Bruce Bailey '59

Bruce Bailey ’59
Distinguished Alumni Award 2023

What does it mean to be alumni? For all of us, there was —or will be — the simple fact of graduating from this institution, each of our specific class years mere pushpins to denote a certain place at a certain moment, a transition that quickly becomes the realm of the past. But for Bruce Bailey, who has been an integral part of the Lakeside community since he began seventh grade here in 1953, alumni is very much an active verb: He has contributed to and enhanced the culture, evolution, and spirit of Lakeside for almost 70 years, and his effortless generosity and irreplicable résumé have bettered every facet of our school. In fact, it was Bailey himself who created the Distinguished Alumni Award in 1971, who wrote the first four citations, and who helped choose many of the recipients. This honor, he says, has typically gone to someone with achievements from without — Lakesiders who have made an impact elsewhere in the world, well outside the bounds of campus. Bailey, as he puts it, is “very much in this place.” And he’s all the more deserving for it.

It is tempting to turn Bruce Bailey into a laundry list of positions and accomplishments, something that he would rather avoid. But the sheer number of his contributions, too many for a single page, beg recognition. He has held 14 different titles at this school, 11 of them as Director, and occupied 14 different office spaces. As a student in the 1950s, he was class president for four years and earned eight varsity letters. As a coach, he took the boys’ basketball team to 13 district and eight state tournaments — and was voted into the Washington State Basketball Coaches Hall of Fame in 2003. As a college counselor for 35 years, he guided thousands of students through their journeys beyond Lakeside. As an educator, he pioneered an economics course and taught it for 20 years. As a constant presence and a jack-of-all-trades, he is the symbol of both our continuity and our willingness to change and improve. Why is commencement held outside? Why are there class retreats? What’s up with the old brass lettering on St. Nick? The answer, inevitably, is Bruce. Chances are, if he isn’t responsible for a tradition or tidbit, he likely knows who is. Along with his nicknames of Mr. Director and Mr. Lakeside, some say he’s Mr. Living Archives, too, a man with an uncanny memory of Lakeside history, people, sport, tradition, and story.

Just walk down the stairs into his home office and it’s readily apparent that Bruce Bailey’s story is Lakeside, and Lakeside’s story is Bruce Bailey: There’s an impressive replica of Bliss Hall, thanking him for 42 years of service. There are at least seven gold plaques for excellent coaching. On one bookshelf sit green spiral notebooks containing detailed player stats from every one of his basketball seasons; if you were to ask him what gives him the most pride, he may well point to those pages and all the triumphs and challenges they represent. In the college counseling office, he adored helping students learn to describe themselves with authenticity, to answer the question: Who are you?

So who is Bruce Bailey? For those who have been lucky to know him, he is a compassionate advisor, loyal friend and colleague, and intuitive leader. For those who don’t, he is something harder to describe: a maker and protector of legacy, a proud supporter, a link between past, present, and future Lakeside. He is a true and distinguished representation of what alumni can be, especially if distinguished also connotes down-to-earth, direct, and self-deprecating. He is, simply put, a legend. But who is Bruce Bailey, according to Bruce Bailey? When pressed, he says, “It might sound kind of corny, but as a coach and teacher I really tried to emphasize the fun factor. That’s why we’re here. I’ve always been a positive person who’s interested in the process, not the outcome. Instead of what can’t we do, I always asked: what can we do?” And if we had to answer back, we’d say: Bruce, with you as our example, we can do everything.

For his decades-long dedication to and outright love for our community, for his impossibly generous service and effective leadership, and for his incalculable impact on generations of students, the Lakeside/St. Nicholas Alumni Association is proud to honor Bruce V. Bailey ’59 with the 2022-2023 Distinguished Alumni Award.

Learn about Lakeside's Distinguished Alumni Award and read citations from recent recipients, including Ruth Kagi ’63Noah Bopp ’92Marjorie Liu ’96, and Lt. Col. Tim Curry ’94here.