Chancellors Pride: 5 Unforgettable Athletes From Valley Regional High School

Sports run deep in Essex-Chester-Deep River, and Valley Regional High School has long been at the heart of it. It’s no surprise some standout talent once wore the Warrior uniform. Today we're celebrating five unforgettable athletes from Chatsworth High School who made a name for themselves well beyond the hometown field.

1. Brian Dayett - Former Professional Baseball Player/Coach

Brian Kelly Dayett was a multi-sport athlete at Valley Regional High School, competing in baseball, soccer and basketball, primarily excelling at baseball. His baseball career continued at Saint Leo College, where he was a standout batter in his two seasons before being drafted by the New York Yankees in the 1978 MLB Draft. Dayett played in the MLB for five seasons for the Yankees and the Chicago Cubs, appearing in more than 200 games. Dayett spent some time playing baseball in Japan before returning to coach professionally for some minor league organizations. Dayett is a member of the Saint Leo University Athletic Hall of Fame. (Sources: MLB, Saint Leo)

2. Olivia Cunningham - Collegiate Basketball Player

Olivia Cunningham was another multi-sport standout at Valley Regional, playing varsity basketball, volleyball and lacrosse during her high school career. She was a key contributor on the team’s 2023 CIAC State Championship run in Class M and provided a huge boost for the team. Cunningham was a member of the boys’ varsity basketball team during her senior season. After the girls’ season was cancelled, she became a team leader and co-captain. She continues her basketball and academic career at Union College, where she is already proving to be a contributor, appearing in every game her freshman year. (Sources: Union Athletics, WTNH)

3. Steve Woods - Retired Multi-Sport Coach

Steve Woods is best known as a longtime football and basketball coach for Valley Regional High School and later on for Old Saybrook. Woods was the head football coach from 1979 to 1996 and led his athletes to strong outputs and shaped the culture in the school. He was named to the Old Saybrook Athletic Hall of Fame in 2025. (Source: Zip06)

4. Maddie Riebold - All-State Soccer Player

Maddie Riebold is known as a girls' soccer standout for Valley Regional High School, All-Shoreline Conference recognition and All-State recognition her senior season, contributing to strong team performances in regional play. She was widely respected on her team and across the league by other teams and coaches. (Source: Zip06)

5. Justin Cheverier - Football State Record Holder

Justin Cheverier was a standout football star for Valley Regional, known for explosive performances and a nose for the ball as a defender. Cheverier set a state record for the most tackles in a career with over 500. His talent was recognized throughout the state, receiving All-Area honors. (Sources: CT Insider)

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