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Master Chief Navy Career Counselor Jason Caldera is a native of San Antonio, Texas. He enlisted in the Navy in July 1998 and graduated from Recruit Training Command and the Fireman Apprenticeship Course, October of that same year. November 1998, Fireman Recruit Caldera reported to his first duty assignment USS Hopper (DDG-70), completing two deployments, Operations Desert Fox and Desert Thunder, and advancing to Electrician’s Mate Third Class. His follow-on assignments included Navy Recruiting District (NRD) San Antonio Sept. 2000 and USS Yorktown (CG-48) April 2001. July 2002, he reported back to NRD San Antonio where he earned the Recruiter Navy Enlisted Classification (NEC) and was subsequently awarded Classifier of the Year.
Master Chief Caldera departed NRD San Antonio January 2006 and reported to USS New Orleans (LPD-18), a pre-commissioning unit, where he served as the Leading Petty Officer for the Training Department and the Assistant Command Career Counselor. After a successful tour aboard the New Orleans, October of 2008 he reported to the Command Career Counselor Course. He graduated in November 2008 and was officially converted to Navy Career Counselor Second Class.
Master Chief Caldera’s first assignment as a Navy Career Counselor was aboard USS Gary (FFG-51), where his duties also included Executive Department Leading Petty Officer, Anti-Terrorism Force Protection (AFTP) Training Supervisor, and the Educational Services Officer. While serving aboard, in 2010 he was selected as the USS Gary, Sailor of the Year.
In 2014, Master Chief Caldera was promoted to Chief Petty Officer while serving aboard USS Fitzgerald (DDG-62). From October 2015 - October 2017 Caldera served aboard USS Blue Ridge (LCC-19) as the Division Officer for three divisions, and from there he was then selected to serve on the COMSEVENTHFLT staff from October 2017 – May 2019. May 2019 Master Chief Caldera transferred to Naval District Washington under a humanitarian transfer to support his wife YNC (ret.) Laura Caldera who was a high-risk pregnancy and diagnosed.
In March of 2022 Master Chief Caldera reported to USS Tripoli, where he served as the Executive Department DLCPO until detaching March 2024 with PCS orders to report to BUPERS-3 to serve as an Enlisted Community Manager (NC/LN/CRF). January 2026 Master Chief Caldera reported to United States Pacific Fleet where he is currently serving as the Fleet Career Counselor.
Master Chief Caldera is a graduate of the Senior Enlisted Academy, Class Brown 235, Sep. 2020 & Columbia Southern University, Associates, Business Administration. His personal awards include the Navy and Marine Corps Commendation Medal, (Seven); Navy and Marine Corps Achievement Medal (Seven); Military Outstanding Volunteer Service Medal; and various unit and campaign awards.