Mr. Chertok’s Journey to Becoming an Assistant Principal


Rosalie Johnson

Chertok waves from his desk phone.

by Rosalie Johnson, Reporter

Alexander Chertok is dedicated to his newfound role as Central Kitsap High School’s new assistant principal. An overseer of academic departments, conflict resolution within the school and bigger projects like Smarter Balanced Assessments or ASB, his general responsibility falls under the umbrella of “reacting to strange things that arise in a school of 1,700 people.” 

Though Chertok was “thrilled” to be offered this position, loved his experience in teaching for South Kitsap School District and was surrounded by educational influences throughout his childhood, pursuing an educational career was never his grand plan.

“I bounced around at the beginning of my college years,” he explained. His first year was at Gonzaga, which was followed by a transfer to the University of Washington. “I was never really focused…I wasn’t really that serious about being in school.”

Chertok eventually dropped out of college and enrolled in the US Navy. However, when he was 24, his military career was cut short by a car accident that broke his back. The following year was focused on physical rehabilitation to heal his injury and completing the military retirement process.

Upon leaving the military and after his car accident, Chertok realized that he had not finished school nor had he been able to finish a military career. 

“That’s not who I wanted to be,” he found. “No matter what I was going to do, I was going to take it seriously from there on out.”

This philosophy stuck with him from that moment throughout his reentry into college – where he enrolled in Portland State University (PSU) – as well as throughout his professional career. At PSU, Chertok focused on English, which had always been his favorite subject.

However, soon into his college experience, Chertok realized that simply enjoying the subject of a class is not a good enough reason to pursue a career teaching it. When it comes to teaching, Chertok carries the belief that the sustenance of the class is not as important as enjoying working with students and treating them with respect: “I think that the people I’ve seen struggle most as teachers and enjoy it the least are those who put content over kids.”

He graduated PSU with a degree in English, a master’s in education and a teaching certificate. 

After Chertok’s 2012 college graduation, South Kitsap High School (SKHS) was one of few schools in need of teachers, so Chertok “packed up and moved” to Washington State.

He filled whatever teaching positions needed to be filled at SKHS during the beginning of his nine years there – though his specialty ended up being AP Senior Literature, which took up the majority of his schedule towards the end of his teaching. “It was a blast. I loved teaching and working with kids,” he expressed.

Around the middle of his time at SKHS, Chertok was elected as the Chair of the English Department, which set him on the path to becoming a principal. Though he enjoyed working in the classroom, he began to focus more on potential leadership roles and making an impact on the school as a whole. He missed the ability to build connections with students and felt a “weird sense of guilt” about leaving the classroom, but he was continually pulled towards the leadership direction.

After receiving a principal certificate from Western Washington University, a position for assistant principal at CKHS opened up within a year. The interview process involved 20-25 people on the interview panel and around 15 questions as well as a follow-up interview with CK district leadership.

The afternoon after the final interview, he received a call that offered him the position. “I was thrilled and super excited. It was just a big long day and it felt sort of surreal, and I was just kind of stunned.”

Chertok’s introductory year at CKHS – or in his eyes, “the best school on the peninsula” – is the first year since 2019 that the school has seen students and staff at full time and capacity. Despite the struggles that students and staff have endured as well as obstacles encountered  (for example, the readjustment to pre-COVID-19 work and engagement levels) Chertok’s vision of opportunity at reidentifying and recreating a culture that best represents CKHS is an “exciting environment to be in.” 

“We have a very real fresh start, a clean slate, in deciding what the culture of our building is, in terms of traditions and who we are as a community,” Chertok explained.

Chertok’s journey to pursuing an educational career has not been easy. The difficulties have shone a light on the importance of not only perseverance, but finding an occupation that allows for joy and opportunities to improve communities – especially after the challenges that the past year and a half have posed to them. Entering this new academic and social atmosphere is uncertain, but Chertok instead looks to the positive change that this uncertainty can be transformed into.

“We have a real opportunity to make this school what we want it to be,” Chertok finalized. “I think it’s pretty special to be a part of a school that is rebuilding all of that.”