John Irving Bailey

John Irving Bailey of Old Saybrook, CT, born March 24, 1943, passed away after a long illness on November 20, 2024 at the age of 81. John survived two major cancers during his lifetime only to succumb to number three. During his battle with cancer, John never stopped working. He continued to spend time with his pilot friends from the old days; friends that John kept in touch with for many decades including, the "Friday Lunch Gang", and of course Joe Jillson his friend since the 4th grade. John wanted to thank his pilot friend doctor; Gary Bertman, MD., and Dr. Bill Hale of Norwalk Hospital for decades of care, research medical advice. Also a special mention of Bob Derosa and Gerry White, two very good friends.

In 1968, he graduated from the University of Hartford earning a Bachelor of Science degree in business and economics and was a member of the University of Hartford Business School Honor Society.

John was a licensed pilot holding an Airline Transport Pilot Certificate and Advanced Flight Instructor Ratings as well as an FAA Airframe and Power Plant Mechanic’s License. He also was licensed as a Federal Aviation Pilot Examiner certifying aspiring airline pilots during the 1980’s and 1990’s.

John was also a musician. He taught himself how to play the piano during high school after being a trumpet player in the elementary school band. While in college, he would often sit in and play the piano at the Rocking Horse Tavern on Franklin Street in Hartford playing popular sing-a-long songs.

One of John's early activities was in auto racing. In the 1960s he worked with his brother and cousin Norm Blodgett entering into racing at the Waterford Speed Bowl in the "Bomber Class". He also won several trophies for cars that he customized and raced at a drag strip in Colchester, CT, often competing with his high school friend the late Louie Dunn.

John started his commercial pilot career with Pilgrim Airlines in the mid 1960’s, before starting a flight school business at the old Waterford Airport with partner, Captain Pete Snyder of U.S . Airlines In 1970, John founded Yankee Airways, a regional air-taxi business, joining up with partner Lt. Thomas Rolf, a former nuclear submariner and pilot. In 1974, he began operating a seaplane and multi-engine flight school in East Haddam. He also operated a seaplane charter and "sky-ride" business on the Thames River in Groton in association with pilot and former newsman Dale Reynolds. In 1978, John went on to co-found Action Air Charters in Groton with partner and Chief Pilot, the late John Rutledge of Pilgrim Airlines. While located at Groton Airport, he later specialized in Multi-Engine airplane instruction and Airline Transport Pilot training specializing in Airline Pilot trainees from all over the world. During the 1970’s and 1980’s, John also served as consultant, pilot and advisor to CityTrust Bank in Bridgeport CT, aiding in the establishment and management of a separate aviation finance division known as City Trust Aviation Group. John was also a pilot for the late Sen. Ted Kennedy on many occasions when called upon. In the 1980’s, John also served on the Bradley International Airport Commission during the Lowell Weicker administration.

In recognition of John's accomplishments in aviation and his 50 year devotion to aviation safety, the Federal Aviation Administration awarded him the distinguished Wright Brothers “Master Pilot” Award in 2017.

After retiring from commercial flying, John became a licensed Private Investigator and opened the John Bailey Investigations Agency in Fort Lauderdale, FL. He specialized in aviation matters. John later expanded investigations to the general public, the legal community and corporations. John was recognized by his peers for preventing and solving criminal and financial crimes for his clients as well as locating missing persons. John remained an active investigator until his recent death.

John was a dog lover and was a one time member of the Springer Spaniel Rescue League, serving at times as a rescue officer and foster home for abandoned dogs. Dali and Casey were his latest Springers that he loved dearly.

John was predeceased by his mother, Kathryn C. Bailey, his father, Robert K. Bailey and an older brother, Robert Bailey. He was also predeceased by his nephew Robert Bailey. John is survived by his life partner, Catherine White, with whom he operated the The Stork & Fashion Exchange in Westbrook, CT. He is survived by his niece, Alisa Marie Bailey of Middletown, CT, and his great nephews, Cameron and Kyle Bailey of Haddam, and their mother Darlene Bailey and their partners. He also leaves behind two great great nieces and a soon to be born great great nephew. John is also survived by Cathy’s father, Kent, her brothers Mike, Gerry, David and Greg and their families.

John and Cathy would also like to remember retired teacher and long time friend, Sharon Schnare, for her unwavering support and loving care during John’s illness.

A private burial for John will be held at the Haddam Cemetery. A Celebration of Life will be held at a later date, where we can tell Bailey Stories and share our memories of this incredible and unique man we all called JB. Rest in Peace JB! In lieu of flowers, please do a random act of kindness in JB’s memory.

Funeral Arrangements are in the care of the Robinson, Wright & Weymer Funeral Home, 34 Main Street, Centerbook, CT.