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Jim Drake has a diverse work experience in the aviation industry. Jim started their career with the United States Air Force in 1979 as an Aircraft Commander F-4E, participating in multiple Air to Ground missions and deployments throughout Europe. Jim then served as an Assistant Chief of Weapons and Tactics, F-4E, leading missions in the politically sensitive Korean Buffer zone and deploying to the Philippines and Japan. Later, they became an Instructor Pilot, F-4E, responsible for providing flight instruction to pilots of varying backgrounds. After joining the Hawaii Air National Guard in 1985, they held various roles including Squadron Pilot, Operations Officer, and Commander, with deployments to locations such as Guam, Korea, Saudi Arabia, and Singapore. Jim continued their military career with the US Air Force Reserve as the Joint Operations Center Director from 2004 to 2006. In 2008, they started working with Aloha Airlines as a Captain until the company ceased operations. Jim then joined USA BMX as a Track Operator for their BMX race track until 2013. In 2014, they became the Chief Pilot at Aloha Air Cargo.

Jim Drake attended the United States Air Force Academy from 1973 to 1977, earning a Bachelor of Science (BS) degree in Civil Engineering. Jim completed Undergraduate Pilot Training in 1978 and went on to attend Fighter Lead In School in 1979. In the same year, they also completed F-4 Replacement Training. In 1981, Jim attended Squadron Officers School for Air Force Leadership Training at the Squadron Level. Jim then completed F-4 Consolidated Instructor School in 1983 and Air Command and Staff College in 1984-1985. In 1987, they attended F-15 Replacement Training. Jim also attended Deployed Commanders Law School and Squadron/Flight Commanders School in 1999. In 2000-2001, Jim attended Air War College, and in 2001, they participated in the Senior Leadership Seminar.