Brian assumed his present position in February 2001 after serving 20 seasons with the club. He served as the head student trainer while earning an athletic training and teaching degree from North Park College in 1982. He is the founder of McCaskey Sportsmedicine Clinic in Mt. Prospect as well as a frequent speaker on sports medicine and athletic training.

Following eleven years as an assistant trainer with the team, McCaskey was named Player Liaison/Operations Assistant in 1993. He has also served as Director of Player and Staff Development involving various player programs with a focus on financial education, degree completion and family assistance. His knowledge of area businesses has been influential in developing the Chicago Bear career internship program.

McCaskey is also the Bears alumni liaison and has formed the Alumni Relations Department, which has created a data base of information of former players. This department also keeps past players informed on current team matters and sends out a quarterly Alumni Newsletter. In addition, he maintains the Bears archives and memorabilia and is working on expanding this program including cataloging of all archive materials.

Since 1999 McCaskey has served as Co-Director of the Bears Training Camp and was a significant part of the successful transition team when it moved in 2002 from Platteville, Wisconsin to Olivet Nazarene in Bourbonnais, Illinois. He is also a member of the Chicago Bears Board of Directors.

McCaskey serves on the Board of Directors of Pickens Kane Moving and Storage Company, is an auxilary officer of the Des Plaines Police Department, and is the Co-Host of the successful fundraiser, Golf for Kids which benefits North Park University’s Outreach Ministry.

McCaskey resides in Lake Bluff with his wife Barb, son Keegan and daughter Kelly.