Pat McCaskey ’68, corporate secretary and vice president of the Chicago Bears, came back to Cheshire Academy for Homecoming Weekend 2025, enjoying dinner with the football team and offering inspiring words before their victorious match-up against Brunswick School.
“He had dinner with us in Bowden Hall, which is big for the kids because they see the connection,” Head Football Coach Bill Mella said of the CA Hall of Famer. “I always say this is team number 129. This is the 129th football team and our alumni are part of that history here.”
McCaskey, who ran cross-country and track while at CA, started working for the Chicago Bears in 1974, after serving as a contributing editor to the literary magazines at both Loyola University Chicago and Indiana University. In addition to his current leadership role with the Bears franchise, he is chairman of Sports Faith International, which recognizes people who are successful in sports while leading exemplary lives. He is the author of 12 books, including Bear with Me: A Family History of George Halas and the Chicago Bears and Sports and Faith: Stories of the Devoted and the Devout.
A 2025 Alumni Achievement Award recipient, McCaskey accepted the inaugural recognition at Cheshire Academy’s Reunion in May. The award is presented to those alumni who have attained outstanding success and national or international distinction in their chosen profession or life’s work, and whose accomplishments reflect admirably on or bring honor to their alma mater.
