In just her first high school season, Medway shortstop Alessandra Cautilli left an imprint on the Tri-Valley League that won’t soon be forgotten. The freshman phenom was named the 2025 Daily News Fans Softball Player of the Year, adding Tri-Valley MVP honors to her growing list of accolades.
Cautilli’s numbers tell the story: .556 batting average, 11 doubles, 25 RBIs, and 8 stolen bases, but her impact went beyond stats. Defensively, she was rock-solid at shortstop, showing range, arm strength, and awareness well beyond her years. Her season reached a high point in the Division 3 Round of 32, where she went 3-for-4, scored three runs, and crossed the plate with the walk-off winner in a 5–4 victory over Cardinal Spellman.
The Mustangs advanced to the Round of 16 before falling to eventual champion Dighton-Rehoboth, but the postseason run solidified Cautilli as a centerpiece for the program’s future. As a rising sophomore and reigning league MVP, she enters next season with both the talent and the mindset to lead Medway toward a championship.
