After graduation, Admiral Highfill completed the Aviation Officer Candidate School in Pensacola, FL and was commissioned an Ensign in the U.S. Navy in 1967, later receiving his Wings of Gold as a Naval Aviator, his lifelong ambition. He spent the next 33 years in the Naval Service, retiring in 2000 at the rank of Rear Admiral. During that time, Admiral Highfill accumulated over 1000 carrier landings, made two combat tours completing 350 combat missions in Vietnam, participated in Operation Desert Storm and Operation Provide Comfort for Kurdish Refugees in Northern Iraq, commanded two carrier aviation squadrons (VAW-117 and RVAW-110), two ships (USS Guadalcanal (LPH-7 and USS Belleau Wood (LHA-3)), and was Operation Officer on USS Enterprise (CVN-65) and Aide to Commander Strike Group SIXTH Fleet in Naples, Italy. As a Flag Officer, he was Vice Director for Command, Control, Computers and Communications (J-6) on the Joint Staff, and Commander Amphibious Forces Seventh Fleet out of Okinawa, Japan. During this period he was awarded the Defense Distinguished Service Medal, the Legion of Merit (4), the Air Medal (6) and 55 other decorations, medals, and campaign ribbons. Admiral Highfill was a Distinguished Graduate of the Naval War College earning a Master of Arts degree in International Security and Foreign Affairs.
Upon retirement from the Navy in 2000, Admiral Highfill settled in Great Falls, VA, where he was appointed as a Vice President for SAIC. Later, he was appointed as a Vice President for C4ISR at the Titan Corporation. He then was appointed as the President and CEO of Base Technologies where, under his leadership, the company was recognized as one of the Top 100 Information Technologies companies in the US. Admiral Highfill was recognized by all who worked for him for his depth of knowledge, attention to detail, focus, hearty laugh, and love of life. He was generous with his time and talents and mentored many along the way. Upon his second retirement, he settled in the Grand Strand region of South Carolina where he worked in real estate, fished, played golf, told tall tales of his many adventures, some of which were true, and, most of all, enjoyed to the fullest his many friends and family.
Admiral Highfill was a loving husband, father, and grandfather. He is survived by his beloved wife, Jenny, his daughter, Cheryl Highfill Woods, her husband, CDR Jeffrey Woods and their three children, Connor, Keira and Kendall of New Freedom, PA; his son, Dr. Jeffrey Scott Highfill, his wife, Dr. Jessica Colburn and their two children, Madeline and Liam of Silver Spring, MD; and his step-daughter, Lauren Jordan Perry of Charleston, SC. He was preceded in death by his beloved daughter, Kristin Leigh Highfill, in 2005 and his faithful companion Boxer, Lucy, in 2015.
Admiral Highfill's family will receive visitors on Sunday, October 14, 2018 from 2-4pm at The Dunes Golf and Beach Club in Myrtle Beach, SC. Burial at Arlington National Cemetery will be held at a later date.
In lieu of flowers, donations can be made to The Ronald McDonald House and The LilaBean Foundation.