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Commander Crosby completed his division officer tours aboard USS LEYTE GULF (CG 55) as Damage Control Assistant, deploying to the Arabian Gulf in support of Operation Enduring Freedom, and Training Officer aboard USS DEWERT (FFG 45) conducting Counter Narcotic Operations in the 4th Fleet AOR. As a department head he was Operations Officer onboard USS O’KANE (DDG 77) home-ported in Pearl Harbor, Hawaii and USS COWPENS (CG 63) forward deployed in Yokosuka, Japan. He was Commanding Officer of Patrol Coastal Crew MIKE and subsequently USS TYPHOON upon the ending of rotational crewing. During his command USS TYPHOON was awarded the 2014 Battle “E” award for Patrol Coastal Squadron One.
During his shore tours he attended Naval Postgraduate School, receiving a Master’s Degree in Systems Engineering Analysis and completing Joint Professional Military Education Phase I. His most recent tour was as Sea Power / Surface Warfare Analyst, in Assessments Division (N81) on the OPNAV Staff.
His awards include the Meritorious Service Medal, Navy Commendation Medal, Navy Achievement Medal and various unit and campaign awards.

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Previous at sea assignments include a tour as Missile Officer in USS TICONDEROGA (CG 47) in Pascagoula, MS where he where he contributed to the ship winning the COMDESRON 14 Gunslinger Award. He later served as Electrical Officer and CIC Officer in USS WHIDBEY ISLAND where he was able to participate in the 2006 Lebanon Non-combatant Evacuation Operations. His Department Head tours were served as the Operations Officer onboard USS OSCAR AUSTIN (DDG 79) and USS LEYTE GULF (CG 55).
Previous shore assignments include Chief Staff Officer at COMDESRON SIX ZERO Detachment Rota, Spain from 2014-2016. Served as Deputy Executive Assistance for Commander, Naval Surface Force, U.S. Pacific Fleet from 2016-2018. Finally served as Strike Officer for Commander, U.S Third Fleet. He received his Master’s degree from the Naval Postgraduate School in Operations Research and completed his Joint Professional Military Education (JPME) Phase I.
His personal awards include the Meritorious Service Medal, the Navy and Marine Corps Commendation Medal (3), Navy and Marine Corps Achievement Medal (2), the Battle “E” Excellence Award and various campaign and service medals and ribbons.

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He reported aboard USS Peterson (DD 969) in Dec 1999 as a Sonar Technician. On the PROUD PETE, he deployed in support of OIF and earned the Enlisted Surface Warfare Specialist before decommissioning PTE in 2002. He then reported to USS Monterey (CG 61) in Nov 2002 where he deployed in support of GWOT
In November 2003, he reported to Naval Recruiting District Kansas City and was assigned to Naval Recruiting Station Rogers Arkansas. There he served as the Recruiter-in-Charge earning the Distinguished Graduate Bakarian Award
In November 2006, he reported to Littoral Combat Ship Pre-Commissioning Detachment San Diego and served as the Leading Petty Officer before transferring to USS Dewey (DDG 105) in April of 2008.
In October 2010, he reported aboard USS Sterett (DDG 104) where he served as CA Division Leading Chief Petty Officer, and deployed twice in support of OND and OEF.
In June 2012, he reported to Commander Naval Surface Atlantic Norfolk, VA where he served as Force Sonar Technician. His follow on orders were Commander Surface Squadron Fourteen Mayport, FL as the Anti-Submarine Warfare Officer in 2015 and in USS The Sullivans (DDG 68) serving as Departmental Leading Chief Petty Officer in 2018. During this time, he earned an Associates Degree in Business, attended the Senior Enlisted Academy, and was selected into the Command Senior Chief Program.
CMDCS Callaway currently serves aboard USS Little Rock (LCS 9) Blue Crew in Mayport, FL as the Command Senior Chief.
His awards include the Navy and Marine Corps Commendation Medal (3), Navy Achievement Medal (6), Navy Good Conduct Medal (6), and various unit and campaign awards.