The Reverend Mr. Thomas Caldwell Bailey, PD of Yarmouth Port, MA and formerly of Branford, CT passed away peacefully on December 26, 2023. He was 102 years old.

Born on November 19, 1921, in Willimantic, CT to the late Theresa Flynn Bailey and Edward Caldwell Bailey. Rev Mr. Bailey was educated in Hartford, CT schools and graduated from Hartford’s Bulkeley High School in 1939.

Like so many of his generation, he enlisted in the United States Army after the bombing of Pearl Harbor and was ultimately assigned to the United States 82nd Airborne Division. In the run up to D-Day he was being trained as a chemical warfare specialist attending the Royal Army School of Chemical Warfare in Wiltshire England when a week before the invasion, all allied military bases went on lockdown.

Unable to return to his unit and jump with the 82nd Airborne, he went over on D-Day with the British in a glider. Over France, the tow plane was hit by German anti-aircraft fire and was unable to release the glider forcing both aircraft back to England. Once on the ground they got off one glider, counted off and then boarded another glider. “They didn’t even give us time to change our underwear,” he frequently quipped.

The second trip ended with his glider crashing not far from the famed Pegasus Bridge, earning him the unique distinction of being amongst a small group of soldiers who invaded Europe twice.

After getting back to his unit he participated in many of the key battles of Normandy, Operation Market Garden and the Battle of the Bulge. In April of 1945, he was ordered into Dachau to secure the gas chamber. A day that haunted him throughout his long life.

After the war, he attended St Bonaventure University earning a degree in Latin American History in 1948. He joined Merrill Lynch’s training class of “nine millionaires kids and me” shortly after graduation working for future Merrill CEO and Treasury Secretary Don Regan as a bond trader.

At Merrill Lynch he met Joan Arnold, an analyst. They married on January 19, 1952.

They moved to New Haven, Connecticut in 1955 and to Branford, CT shortly thereafter. Mr Bailey joined Harris Upham & Co in the early 1960’s and retired from Smith Barney Harris Upham in 1988.

In 1985, he was ordained a member of the Permanent Deaconate in the Archdiocese of Hartford. Upon moving to Yarmouth Port in Cape Cod he became a Deacon of St Pius X parish in South Yarmouth, MA where he remained until his death.

Deacon Bailey leaves his wife of 72 years, 11 months and 7 days Joan Arnold Bailey, three children, Alice Bailey Boyd of Scituate MA, Thomas Caldwell Bailey Jr (Mary Jo) of Dedham, MA and Richard D Bailey (Christina) of Scituate, MA. In addition to his children, he leaves nine grandchildren and eight great-grandchildren.

He was known and will be remembered by family and friends for having a song for every occasion, frequent and regular outbursts of poetry (especially Kipling) and incorrigibly slipping cash to his grandchildren.

Calling hours will be held at Hallett Funeral Home, 273 Station Ave, South Yarmouth, MA on Tuesday, January 2, 2024 from 3-5 p.m. A Mass of Christian Burial will be held on Wednesday January 3rd 2024 at 10:00 am at St. Pius X Church, 5 Barbara Street, South Yarmouth, MA with full military honors burial shortly thereafter at Chandler Gray Cemetery.