Hailing from Davis, California, CDR Easterday graduated from the United States Naval Academy in 2001 with a Bachelor of Science Degree in History. As a division officer, CDR Easterday served as ASW Officer aboard USS GARY (FFG-51), in Yokosuka, Japan and as Assistant Officer in Charge / Operations Officer of MOBILE SECURITY DETACHMENT SEVEN ONE in Guam. Among other missions during this tour, he deployed aboard USNS MERCY (T-AH 19) conducting humanitarian relief operations in the aftermath of the 2004 South Asian Tsunami and later aboard USNS GYSGT FRED W. STOCKHAM (T-AK 3017), conducting counter-terrorism operations in support of Joint Special Operations Task Force - Philippines. Following Department Head school, he served as Operations Officer in USS PREBLE (DDG 88). In 2011, CDR Easterday took command of PATROL COASTAL CREW LIMA, embarked successively in USS HURRICANE (PC 3), USS THUNDERBOLT (PC 12), USS SHAMAL (PC 13), USS SIROCCO (PC 6), USS TORNADO (PC 14) and USS MONSOON (PC 4), deploying twice to the FIFTH Fleet Area of Operations and overseeing the first homeport shift of a Patrol Coastal crew to the Kingdom of Bahrain. He served as Executive Officer in USS JOHN S. McCAIN (DDG 56) from December 2017 to June 2019.
Ashore, CDR Easterday served as an Ocean Systems Watch Officer and Quality Assurance Officer at the Joint Maritime Facility, St. Mawgan, UK, and as a Logistics Operations Planner at Special Operations Command, Africa. CDR Easterday is a graduate of the Advanced Command and Staff Course at the Defence Academy of the United Kingdom's Joint Services Command and Staff College, and has a Master's Degree in Defence Studies from King's College, London.
His personal decorations include the Defense Meritorious Service Medal, Navy Commendation Medal and Navy Achievement Medal as well as various unit and campaign awards.