Command Master Chief Robert McGregor is a native of Cimarron, KS and graduated from Cimarron High School in 1995.

He entered the United States Navy on 18 July 1996 and attended Recruit Training and Basic Engineering Common Core in Great Lakes, Illinois and Damage Controlman “A” School at FTC San Diego, CA.

His sea tours include; Repair Division LPO onboard USS Avenger (MCM 1) in Ingleside, TX, Repair LCPO onboard USS Crommelin (FFG 37) in Pearl Harbor, HI, Repair LCPO onboard USS Forrest Sherman (DDG 98) in Norfolk, VA where he qualified as Engineering Officer of the Watch. Most recently, CMDCM(SW) McGregor served as the Senior Enlisted Leader and MOB-D Material Assessor at Commander Destroyer Squadron THREE ONE in Pearl Harbor, HI.

Shore Tours include: Mine Warfare Training Center/Center for Naval Engineering Ingleside, TX as Leading Instructor at the Fire Fighting/Damage Control School, Senior Enlisted Leader at NOSC Sioux Falls, SD and NOSC Wichita, KS, and Force 3MC/Surface Programs LCPO at Commander Navy Reserve Forces Command. As an Individual Augmentee, Master Chief McGregor served nine months in Iraq with Navy Provisional Detainee Battalion Six as the Senior Non-Commissioned Officer-In-Charge for Compound 17 at Theatre Interment Facility Camp Bucca, Iraq.

Master Chief McGregor participated in EURO 97 and EURO 99 deployments to the North Atlantic and Mediterranean. He participated in Joint Warrior exercises in 2010 and 2012, Flag Officer Sea Training with the United Kingdom’s Royal Navy in 2012, and a 9 month deployment in support of Operation Active Endeavor in 2012. He has completed a deployment to the South Pacific in support of Counter-Narcotics Operations and UNITAS 45-04 and a deployment to the Western Pacific where he participated in CARAT 2006.

His personal awards include a Bronze Star, Meritorious Service Medal, Navy and Marine Corps Commendation Medal, Navy and Marine Corps Achievement Medal, and various unit awards and commendations. Master Chief McGregor is a Master Training Specialist, a graduate of the Senior Enlisted Academy (BC 55), and the CMC/COB Course Class. In 2017, he received his Bachelor’s Degree in Emergency and Disaster Management.

Master Chief McGregor reported to Patrol Squadron 69 in February of 2022. He attributes all of his personal awards and successes to his family, mentors and the Sailors with whom he had proudly served exemplifying the Navy's Core Values.​​​​​