John Conway Gleeson

Honoring the Life of a Hero: An Ordinary Man Who Did Extraordinary Things

Obituary

John Conway Gleeson, a revered Hawaii aviation legend, WWII and Korean War veteran, and most importantly to him, a man of deep faith in Christ, passed peacefully on January 15, 2026, at the age of 102, surrounded by loved ones. Born in Mitchell, South Dakota, he later became a longtime resident of Honolulu, Hawaii, where he devoted his life to aviation, community, and service.

John grew up in Long Beach, California. The day after the attack on Pearl Harbor, December 8, 1941, he recalled feeling “a wave of patriotism” and knew he had to join the fight and help his country and fellow man. He enlisted in the United States Army Air Corps and went on to serve as a B-24 flight engineer and top turret gunner with the 8th Air Force, flying perilous bombing missions over Europe during World War II.

One of the most extraordinary chapters of his service was his time with the OSS, the predecessor to the CIA and Special Forces, where he was selected for undercover missions as part of Operation Carpetbagger. He and his crew flew black-painted, “civilian-looking” aircraft on covert nighttime missions to deliver ammunition and supplies to Norwegian underground resistance fighters in Nazi-occupied Norway. These missions were conducted without fighter escort, relying solely on darkness, precision, and courage.

After World War II, John met and married the love of his life, Barbara, and together they went on to raise three beautiful daughters. He earned his civilian pilot’s license in 1947, witnessed Howard Hughes’ first and only flight of the Spruce Goose, and continued flying throughout his life with both the Civil Air Patrol and the U.S. Coast Guard Auxiliary. During the Korean War, he reenlisted in the military, continuing a lifelong devotion to aviation and service to his country. In recognition of his lifetime of flying, he was awarded the FAA Master Pilot Award in 2006.

John was a founding member of the Pearl Harbor Aviation Museum, and throughout his centenarian years remained an active and beloved volunteer, hosting weekly meet-and-greet and storytelling sessions where visitors could ask questions and hear firsthand about his time in service. He was also a proud ambassador of the veteran nonprofit Beyond The Call, participating in numerous programs and events throughout the year and leaving a lasting impression on all who spent time with him and heard his stories. He had the honor of representing the state of Hawaii as the only WWII veteran from the state to attend the 80th Anniversary Commemoration of D-Day in Normandy, France, hosted by American Airlines, accompanied by his daughter, Colleen.

John never met a stranger. Known as “Mr. Sunshine” at his assisted living facility, he brought warmth, laughter, and life wherever he went, filling the halls with stories, smiles, and genuine kindness. 

A successful entrepreneur, John ran several businesses and founded John Gleeson Limited, while also serving in numerous civic leadership roles, including chairman positions with planning commissions, civil service commissions, and the Reno/Sparks Hydroplane Regatta. He organized major aviation and community events, including the Great Hawaiian Air Race benefiting the Make-A-Wish Foundation, supported Civil Air Patrol cadet programs, and helped bring aviation history to life for countless people across generations. He continued to fly up until his very last year of life.

Above all, John loved his family and was most proud of them. He was known for his honesty, loyalty, and unwavering integrity. His word was his bond. A man of deep faith, he took great comfort in his final days knowing he would soon be reunited with the Lord and his beloved wife of 75 years, Barbara.

John is survived by his daughters Colleen Roe (Bill) and Cathleen Gleeson (David Maughan); his grandchildren Katie Forman, Alex Kochis, David Roe, Joshua Roe, and Beth Graves; 11 great-grandchildren; and one great-great-grandchild. He is preceded in death by his wife, Barbara Gleeson; his daughter, Maureen Reynolds (Ron); and his granddaughter, Amy Davenport.

John was deeply loved by his community and meant a great deal to so many. He gave endlessly of his time and heart, and his presence filled our lives with meaning. He reminded us not only of the sacrifices of the Greatest Generation, but also of the kindness, humility, and courage that defined it. He left this world better than he found it, and his legacy will be carried forward with gratitude and honor.

Gallery

Memory wall

January 27, 2026

On behalf of the Board of Trustees, volunteers and staff of the National Museum of the Mighty Eighth Air Force, we extend our deepest and heartfelt sympathies to the family of John Conway Gleeson. He represented the courage, character and patriotism displayed by the men and women of the Eighth Air Force.

National Museum of the Mighty Eighth Air Forc

January 25, 2026

I was fortunate enough to be one of John Gleeson’s hospice nurses. He would regale me with wonderful stories of his life. My favorite was when he went AWOL & danced with Betty Grable. Another was how & when he met his wife. She was surrounded by a few young men & John told ‘em to “get lost.” And they left immediately! As I learn more about John, I realize how humble he was. He could have bragged about his dangerous missions but he never did. Of course he told me that he was in combat, but I am flabbergasted to read the extent of his service. He is one in 8 billion.

Hannah Hurvitz

January 21, 2026

There is an old saying,”When a wise man dies a library burns to the ground.” There isn’t a library big enough to contain John’s life.

John Frauens

January 21, 2026

We are so blessed to have met you and so lucky to live in your beloved condo. We will always remember your warm visits to your old home. We feel your presence and you inspire us all. We love you and miss you! - Shirley & John

Shirley Xiaoyi Sun

Service