For Captain Rich O’Sullivan, aviation was not the original plan. A summer training cruise aboard a Navy submarine quickly revealed he was claustrophobic, prompting a change in course that launched a remarkable four-decade career in aviation.

Today, Rich brings that wealth of experience to Delta Professional Services (DPS) as a B767/757 Instructor supporting DHL Guatemala in Miami. With more than 18,000 flight hours and an exceptional safety record, he remains passionate about helping the next generation of pilots grow and succeed.

Rich graduated with honors from the U.S. Naval Academy in 1977 with a Bachelor of Science in Ocean Engineering. He would go on to further his education with advanced degrees from the U.S. Naval War College and Salve Regina University while building a career dedicated to service and aviation.

After realizing life aboard submarines wasn’t for him, Rich set his sights on the skies and embarked on a 20-year career as a Naval Officer and Aviator in the U.S. Navy.

From 1977 to 1997, Rich flew the P-3 Orion, a long-range maritime patrol aircraft, and served as a Patrol Plane Commander, Mission Commander, and Instructor Pilot across multiple squadrons.

One of the highlights of his Navy career was commanding Patrol Squadron Five (VP-5), a 350-member frontline squadron responsible for global P-3 operations in support of national defense missions. Throughout his service, he earned numerous military honors, including the Defense Meritorious Service Medal, Meritorious Service Medal, and Navy Commendation Medal.

Following his retirement from the Navy, Rich joined Delta Air Lines in 1997 as a First Officer on the B737. Less than two years later, he upgraded to Captain on the Delta Express operation.

His passion for teaching quickly became evident. As Seniority List Instructor, Rich trained new hire first officers and newly upgraded, earning his reputation for going “the extra mile” for his students and the company.

Over the next 17 years, Rich flew the B757 and B767 as both First Officer and Captain, based in New York. He led flight crews with a strong focus on safety, professionalism, and Crew Resource Management (CRM) principles.

He later served as a Line Check Airman (LCA) for the B757/767 fleet, conducting more than 200 line checks and operating experience evaluations. In that role, he helped ensure pilots met operational standards while reinforcing the importance of Safety Management System and threat mitigation.

When Rich reached the mandatory airline retirement age of 65 in 2020, he wasn’t ready to leave aviation behind.

Encouraged by friends in Delta’s Flight Standards Department, he joined DPS in 2021 and trained as a simulator instructor. Over the next two and a half years, he instructed pilots on the B767 and B757 before transitioning to the DHL Guatemala client group in Miami in January 2024, while also supporting the ATP-CTP program in Atlanta.

Today, Rich is endorsed by Guatemala’s aviation authority (DGAC) to administer proficiency checks to DHL Guatemala pilots and consistently receives outstanding feedback from trainees and fellow instructors.

“My favorite thing about teaching is when the ‘lightbulb comes on’ and my student finally grasps the concept I am trying to teach. It has been especially rewarding working with the DHL Guatemala pilot group alongside fellow DPS’ers Mike Maguire and Fred Gackerheimer,” he shared. “The DHL pilots, led by their Training Captain Gerardo Berganza, have been super enthusiastic and eager to learn what we have to offer. They are a pleasure to teach.”

Rich also gives back through his work as a U.S. Naval Academy Blue and Gold Officer, where he mentors prospective students and coordinates outreach efforts throughout Central and Northeast Florida.

When he’s not in the simulator, Rich enjoys spending his life with Allison, his wife of 48 years in Orlando, Florida. Together they enjoy traveling, cruising, staying active, and making memories with their son Andrew, daughter-in-law Lucy, and two grandsons in Memphis, Tennessee.  

After more than 40 years in aviation, Rich’s passion for flying has evolved into helping others reach new heights. Whether in the cockpit, the classroom, or the simulator, he continues to make a lasting impact on every pilot he teaches.