John Caiola

John L. Caiola

1950 - 2020

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Obituary of John L. Caiola

John L. Caiola, age 70 of Fairfield, beloved husband of the late Donna Boland Caiola, died peacefully on Monday, June 1, 2020 with his loving family by his side. Born in Bridgeport on January 1, 1950, he was a son of the late Joseph M. Caiola, Sr. and Dolores Plante Caiola. Mr. Caiola was raised in Bridgeport and was a 1967 graduate of Central High School. He was a proud U.S. Navy Veteran of the Vietnam War and worked as truck driver for Standard Oil, and the Dalling, Brennan and Durante Construction Companies, until the time of his retirement. An avid collector of antiques and old toys, he was often found rummaging his way through flea markets and garage sales in search of aged and worn treasurers. Upon finding such gems, he would artfully and skillfully negotiate a price, never committing to the transaction until he tipped the scale, just slightly in his favor. Mr. Caiola was a lifelong automobile enthusiast and enjoyed attending area cruises and classic car shows, often followed by an evening at Pepe’s Pizza for his favorite pie. John will be long remembered as a loving father, poppi, uncle and moreover, as a loyal brother and friend. He is survived by his devoted daughters, Dana (Rob) Merchant of Fairfield and Tara (Zach) Pacacha of Shelton; twin brother Joseph (Debra) Caiola of Trumbull, Paul (Ruthann) Caiola of Monroe and Randy (AnnaMarie) Caiola of Trumbull; a sister, Joelle Caiola of RI; grandchildren, Sean Merchant of Fairfield, and Jake, Ava and Maddon Pacacha of Shelton; and God-daughters, Amber Caiola of Milford, Joanna Rosen of Trumbull and Jenelle Bartel of Orange; as well as many nieces, nephews and his feline friends, Zoey and Missy. A graveside service with Military Honors will be held on Thursday, June 4, 2020 at 10:00 AM in the Long Hill Burial Grounds, Middlebrooks Ave., Trumbull. Memorial contributions may be made to the Swim Across the Sound, St. Vincent's Medical Center Foundation, 2800 Main Street, Bridgeport, CT 06606, The Wakelee Memorial Funeral Home, 167 Wakelee Avenue, Ansonia is in care of arrangements. Online condolences may be made at

Graveside Service with Military Honors

10:00 am
Thursday, June 4, 2020
Long Hill Burial Ground
Middlebrooks Ave.
Trumbull, Connecticut, United States

Memorial contributions may be made to:

Swim Across the Sound, St. Vincent's Medical Center Foundation, 2800 Main Street, Bridgeport, CT 06606,