Kyle Cassamas

Since 2017, Kyle Cassamas has served as the leader of the Stevenson Pirates football program, turning it into one of the most respected and competitive small-school teams in the Central Coast Section.

His leadership has brought a new standard of discipline, toughness and player development to the program, one that is now recognized across the PCAL and beyond.

Over the past eight seasons, Kyle has compiled an impressive 36–28 overall record, including a dominant 32–6 mark in league play. Stevenson has captured two PCAL division championships, with undefeated league seasons in both 2022 and 2024, and just one league loss over the past three years. The Pirates have become the standard for consistency and competitiveness.

Defensively, Kyle has built a unit that not only dominates in a single season but consistently ranks among the best in the PCAL year after year. Recent seasons reflect the program’s defensive evolution:

• The 2024–25 season was a defensive high mark with just 12.3 PPG allowed (fewest in the division) and a dominant +17.9 average margin.
• Historical data (ratings from 2017–2024) places Stevenson among the top defensive programs in the region, underlining Kyle’s sustained impact on the program’s identity and results.

Off the field, Kyle is known for his mentorship and long-term investment in student-athletes. More than 20 Stevenson football athletes have gone on to compete at the collegiate level, from Division III to Division I. Recent graduates Evan Johnson (BYU) and Charles Du (Notre Dame) are finding success both on and off the field, exemplifying the values developed within the Stevenson program.

Kyle’s coaching career began at his alma mater, The Moses Brown School, where he contributed to the development of several future college standouts – linebackers and edge rushers who went on to play at schools like Stanford, Brown and Penn, with one player eventually reaching the NFL and now working for the New Orleans Saints. These formative coaching years laid the foundation for the values and principles that define his program today: discipline, preparation, resilience and belief.

At Stevenson, Kyle has dramatically grown participation at both the varsity and JV levels, assembled a loyal and talented coaching staff, and instilled a culture rooted in accountability, pride and growth. He is also Stevenson’s director of summer & auxiliary programs, a dorm head and father to two Stevenson Pirates, Quinn and Clover. He resides on campus with his wife Megan and their children, and is a dedicated contributor to every facet of the Stevenson community.