Cheshire Academy

Cheshire, CT

NEPSAC Class AA

9 players

Program Scout Report

Overview

Cheshire Academy stands as one of New England's premier prep basketball programs, competing at the highest level in NEPSAC Class AA. With a foundation dating back to 1794, the institution combines historic academic excellence with elite athletic development, attracting top-tier prospects from across the nation.

Coaching Staff

The program maintains a commitment to developing complete student-athletes through disciplined coaching and comprehensive skill development. The coaching staff emphasizes both fundamental basketball principles and character building, preparing players for success at the collegiate level and beyond.

Player Development

Cheshire Academy has established itself as a reliable pipeline to Division I basketball programs, with a track record of placing players at competitive college levels. The program's development system focuses on maximizing individual potential while building team chemistry, as evidenced by their consistent ability to attract and develop elite prospects across multiple graduating classes.

Culture & Academics

The academy provides a structured boarding school environment that balances rigorous academics with high-level athletics. Students benefit from small class sizes, dedicated faculty, and state-of-the-art facilities that support both educational and athletic pursuits.

Recruiting Outlook

The current roster features strong depth with nine tracked players, highlighted by a promising 2026 class including James Caldarella, John Spinoso, Justin Brown, Dillon Hinkson, and Jeremiah Medor. This talented core positions the program well for continued success in NEPSAC Class AA competition while maintaining its reputation as a destination for serious college basketball prospects.

Analysis by PrepRadar Scouting Team