A native of San Diego, California, Commander Caskie graduated from San Diego State University in 2008, earning a Bachelor of Science degree in Business Administration. Commander Caskie was commissioned through Officer Candidate School and reported to NAS Pensacola, Florida for flight training in May 2010. He earned his “Wings of Gold” in December 2011.

Commander Caskie’s operational assignments include HSM-70 “Spartans” where he deployed to FIFTH and SIXTH FLEET aboard USS GEORGE H.W. BUSH (CVN 77) and USS Roosevelt (DDG 80), participating in Operation ENDURING FREEDOM and Operation INHERENT RESOLVE; HSM-35 “Magicians” where he served as Detachment ONE Officer in Charge deploying aboard USS MOMSEN (DDG 92) in support of FIFTH and SEVENTH Fleet Operations. He also served as the Aviation Safety Officer, Safety Department Head, and Maintenance Officer.

Commander Caskie’s shore assignments include the HSM-41 “Seahawks” where he served as an MH-60R Fleet Replacement Squadron Instructor Pilot. Following his instructor assignment he was selected for the Fleet Scholar Education Program, graduating with a Master of Business Administration degree from San Diego State University. Additionally, he was assigned to United States Central Command, J3 Operations Directorate as a Action Officer directly supporting multiple named operations in the Area of Responsibility.

Commander Caskie has accumulated over 2,200 flight hours with 1,900 flight hours in the MH-60R. His personal awards include the Defense Meritorious Service Medal, Navy Commendation Medal (2 awards), Navy/Marine Corps Achievement Medal, and various unit and campaign awards. He and his wife, Ashley have 2 children.
 

Last Updated: 15 January 2026