Coach McCaskey enjoyed his playing days at Paramus Catholic Boys High School during the nascency of New Jersey high school hockey where he was the Varsity team’s Captain. In the 1990s, Coach McCaskey served as a consultant to USA Hockey which included speaking engagements at coaches and referee clinics throughout the Atlantic District. Coach McCaskey also previously served as President of Ramsey Hockey Association which not only developed youth hockey in the Ramsey community but assisted in administrating Ramsey High School’s ice hockey program which captured two public division State Championships.

More recently, Coach McCaskey was on Coach Keough’s staff as an assistant coach for Bergen Catholic’s Varsity hockey team which captured two County Championships and two League Championships, had two alumni selected in the NHL entry draft and seven players recruited by Division I NCAA programs. Over the years Coach McCaskey has coached numerous hockey teams from the Mite through Midget age classifications which included Tier I level teams. Coach McCaskey is a USA Hockey Level 4 Certified coach and has served as a Level 3 Certified official.