Thomas John Flanagan, Sr., 92, of Madison and Ridgefield, beloved husband of the late Jane Frances Erickson Flanagan, died peacefully Nov. 12 in Branford. He was born Nov. 15, 1942 in Somerville, Massachusetts to the late Michael Flanagan and Bridget “Delia” McCarthy Flanagan of Ireland. 

Mr. Flanagan was a graduate of Boston College High School and Boston College and served on the board of trustees for his beloved alma mater. He attended Columbia Graduate School of Management at Arden House, along with further graduate studies at Harvard and Oxford in air transportation. He joined the Civil Pilots Training Program at Boston College at the start of World War II, where he discovered his love of flying.

He was hired by Pan American World Airways and served in the United States Navy as a pilot during World War II. After his wartime service, Captain Flanagan continued his aviation career with Pan American World Airways out of JFK and the Pan Am Building for more than 45 years. He befriended many VIPs throughout his career, including Juan Trippe, Charles Lindbergh, Willy Brandt, “Tip” O’Neill, Maureen O’Hara and Charlie Blair; and meeting Presidents Reagan and Bush Sr., as well as many other dignitaries from around the world. 

By the end of his distinguished career, he had flown aircraft ranging from “clipper” ships (flying boats) to the Boeing 747, and served in more than 20 executive administrative roles, continually rising through the ranks of management. He was appointed Senior Vice President of Operations, International Affairs, Far-East Operations, and Assistant to the President, to name a few. He was responsible for introducing the 747 into airline service, for negotiating hostage crises, and for opening flight routes into China. In 1978, he started Pan Am World Services Inc., a wholly owned subsidiary of Pan Am and was president and CEO of this $500 million venture until his retirement.

Captain Flanagan received several awards for his military and aviation career including The Commanders Cross of the German Order of Merit from the German government, for his outstanding work in connection with service to Berlin during the Berlin Airlift from 1953 to 1961, and a Certificate of Merit from the United States Department of Defense General Westmoreland, as Director of the R&R project for outstanding contributions to the morale and welfare of the troops in Vietnam from 1966 to 1969. He served Pan Am well in its mission to unite the world and was truly a member of the “Greatest Generation.” Loving uncle, godfather, friend and mentor to many. He will be deeply missed.

He is survived by his daughter Elizabeth (Flanagan) Viloudaki of Madison; his son Thomas J. Flanagan, Jr., and his wife Kimberly of Dunstable, Massachusetts; and grandchildren Eva Grace and Thomas J. Flanagan III of Dunstable; and Emily Jane and William James Viloudaki of Madison. He was predeceased by three sisters, Rita Foley, Josephine Fallon, and Mary Tighe; and two brothers, Francis and James Flanagan.

A Mass of Christian burial will be celebrated Saturday, Nov. 16 at 12 p.m. at St. Margaret’s Roman Catholic Church, 29 Academy St, Madison. Burial with military honors will follow in West Cemetery, Route 1, Madison. In lieu of flowers, contributions in Captain Flanagan’s memory may be made to the Asthma and Allergy Foundation of America, 8201 Corporate Drive, Suite 1000, Landover, MD 20785, or online at www.aafa.org, or to the Wounded Warrior Project, P.O. Box 75817, Topeka, KS 66675. The Guilford Funeral Home is in charge of arrangements. www.guilfordfuneralhome.com