Caskey graduated from the Indiana University of Pennsylvania Police Academy in May of 1988. Immediately after graduation he was hired as Assistant Chief in Smethport serving in that post from May of 1988 to January of 1990. In January of 1990 Caskey started his career in the City of Bradford as a patrolman. In 2005 Caskey successfully completed the civil service testing procedure for the rank of Lieutenant. In February 2006 Caskey was promoted to the rank of Lieutenant and placed in charge of six men working the night shift. During his time as a Lieutenant Caskey has handled payroll, scheduling and has been involved in policy decisions.
Caskey is a member as well as a past President and Secretary/Treasurer for the William Hanley Sr., Fraternal Order of Police. During his time in those offices he was part of a negotiating committee that successfully completed contracts between the F.O.P. and the City of Bradford. Caskey is also a member and Past Master of Liberty Lodge #505 F&AM of Port Allegany. He is also a member of the United Methodist Church in Port Allegany and Pine Acres Golf Club in Bradford. He has been a volunteer coach for Little League baseball for 8 years and Midget/Pony football for 5 years.
Caskey is a lifelong resident of McKean County. He was born and raised in Port Allegany, where he lived until starting his career in Smethport. He is married to Debbie (Crattie) Caskey and has 2 sons Donald age 16 and Patrick age 12. The family resides in Bradford.