In 1996 he reported to the HSL-42 “Proud Warriors” where he deployed as Detachment SIX Training Officer in USS NICHOLAS (FFG 47) and Maintenance Officer for Detachment FOUR in USS DEWERT (FFG 45). While not deployed he served as Squadron Assistant Operations Officer and Quality Assurance Officer.
Captain O’Brien reported to HSL-40 in 2000 as a SH-60B Fleet Replacement Squadron Instructor Pilot. During his tour, he served as Training Schedules Officer and Assistant Training Officer and was recognized as the Naval Helicopter Association’s 2001 Instructor of the Year.
In 2002, Captain O’Brien returned to sea duty as Assistant Air Operations Officer for Captain Carrier Strike Group TWELVE in USS ENTERPRISE (CVN 65). He qualified as Flag Tactical Watch Officer and Battle Watch Captain, deployed to the Arabian Gulf and directed combat operations across the entire CENTCOM area of responsibility.
Captain O’Brien’s next assignment was with the “Vipers” of HSL-48 where he deployed as Officer in Charge Detachment SIX in USS O’BANNON (DD 997) to the North Atlantic and Mediterranean Sea. Ashore he served as Squadron Maintenance Officer. In November 2005 he was ordered to Naval War College in Newport RI where he graduated with distinction, earning a Master of Arts Degree in National Security Studies. Following graduation he reported to The Joint Chief’s Staff in Arlington VA where he served as an Action Officer and the Executive Assistant to the he deputy Director for Resources and Acquisition in the J-8 directorate.
In March 2010, Captain O’Brien assumed the duties of Executive Officer of the “Swamp Foxes” of Helicopter Anti-Submarine Light FOUR FOUR (HSL-44) where he completed a transition to the MH-60R helicopter. In June 2011, CAPT O’Brien became the first Commanding Officer for Helicopter Maritime Strike Squadron SEVEN FOUR (HSM-74).
Following a successful command tour, Captain O’Brien was assigned as Navigator in USS GEORGE H. W. BUSH (CVN 77) where he deployed to the Arabian Sea and Arabian Gulf supporting combat operations in Afghanistan, Iraq, and Syria.
Captain O’Brien has been awarded the Defense Meritorious Service Medal, the Meritorious Service Medal, Navy and Marine Corps Commendation Medal, Navy and Marine Corps Achievement Medal and various campaign, unit, and Service awards. He has logged over 2500 flight hours and hundreds of small deck landings in the SH-60B and MH-60R.