Colonel McCaskill is from Tallahassee, Florida. He earned a Bachelor of Arts in Political Science from Florida A&M University and a Master of Arts in International Affairs from George Washington University. He graduated from the Infantry Officer Basic and Quartermaster Advanced Course, Command and General Staff College, and the Army War College.
His key logistical assignments included: Transportation and Quartermaster Platoon Leader, 3rd Supply and Transport Battalion; Depot Commander, 596th Quartermaster Petroleum Depot Company; Deputy Branch Chief, Defense Contract Administration Services District, Reading, Pennsylvania; Province Logistics Advisor, Vietnam; Security Assistance Instructor, Army Institute for Military Assistance, Fort Bragg, North Carolina; Executive Officer, 260th Quartermaster Battalion (Petroleum Supply), Fort Stewart, Georgia; Executive Officer, Quartermaster Brigade and Commander, 240th Quartermaster Battalion (Petroleum Operating), Fort Lee, Virginia; Director of International Logistics, Army Tank-Automotive Command, Warren, Michigan; and concurrently in the Pentagon, as Deputy, Installation Assistance (Installations and Logistics), and Director, Installation Assistance Agency.
As both Deputy and Director of Installation Assistance Agency (Installations and Logistics) at the Pentagon, he exercised staff oversight, policy guidance, and implementation over the Army’s Model Installation and Commercial Activities Programs. The implementation of both programs resulted in in a cost saving of over $500 million dollars by Army installations world-wide in operations and maintenance costs. As Director of TACOM International Logistics Program, he increased the outreach and value of the program from $500 million to $2 billion for Security Assistance to allies with logistical support that included tank and automotive equipment. As a Petroleum Depot Commander in Thailand and Province Senior Advisor, Military Assistance Command Vietnam, he led a major refuel capability for aircraft in Thailand and Vietnam Theater of Operations, and performed quality assurance testing of all fuels used. He advised and assisted his Vietnamese counterpart in improving deficient logistics and civil affairs operations.