WILTON — Colum (Joseph) O’Brien died peacefully at home on January 10, 2024, surrounded by his loving family. Colum was born on March 17, 1944, in Dublin, Ireland, to Patrick and Bridget O’Brien. Colum grew up in Ireland surrounded by the family chaos of 11 children. He served his apprenticeship as a jockey in Lambourne, England, and met the love of his life, Jacqueline (Ward) while visiting home in 1961. Colum and Jackie started a long-distance love affair that included many love letters between them. Colum came to the United States in 1964 to work with his brother Leo and eventually emigrated fully in 1966. He was with his older brother Leo, and soon joined by another brother Michael. Together they became known on the riding circuit as the “Jumping O’Briens” and they successfully fulfilled their dreams of becoming steeplechase jockeys. 

On February 3, 1968 Colum and Jackie wed in Middleburg Virginia, and their first daughter Michele was born in Leesburg, Virginia in December of 1968. Their second daughter, Colleen, arrived in February of 1974. In 1978, Colum switched careers and became a thoroughbred horse trainer. He started training at Belmont Park, in Elmont, NY. Training and riding his own horses were Colum’s passion and calling in life. Throughout his 40-year career as a horse trainer, he traveled the East Coast winning races, mostly in New York. His favorite place to train and race was Saratoga Springs. He was a true horseman and loved to ride the horses that he trained, in fact, he continued to ride well into his early 70’s. He retired from training horses in 2017 and left Elmont to retire in Saratoga Springs with his wife Jackie.

To know Colum, was to love him. He was a charismatic man who loved to talk to everyone. He enjoyed sharing his views and laughing with all. His pride and joy were his three daughters, Michele, Colleen, and Tara (who arrived in August of 1980). His greatest achievement was ensuring that his daughters got the best education possible. All three girls went on to college and had successful careers. Colum never met a stranger, he welcomed all into his barn and his home.  He gave many of today’s leading riders their first shot. He loved everything about the horse industry and loved to travel to farms to see the young horses and how they were developing. He also made sure to find the retiring horses he trained loving second careers or homes.

Colum’s greatest skill was unconditional love, both with his wife, his daughters and his grandchildren. One of the unique aspects of this love was involving his whole family in his career as a horse trainer. Jackie often brought the three girls to the barn to “help” out when they were younger. As his daughters got older, they worked with their Dad at the barn on the weekends and school holidays. All three of his daughters spent time with him and learned every aspect of the business. He taught them how to ride, but most importantly he shared his passion and love for horses with them. The O’Brien family was always together at the barn and at the races. And when Colum won a race, it was a family affair and celebration. He continued that tradition of sharing his love of horses with his three grandchildren, Bridget, Keellyn, and Angelo. Many mornings you would see him proudly giving his grandkids pony rides around his barn.

Colum is survived by his wife Jacqueline (Ward), his daughters Michele (Angelo Vescio), Colleen (Jay Cummings), and Tara, and his grandchildren Bridget and Angelo (Vescio) and Keellyn (Cummings). In lieu of flowers, the family asks for donations to the Thoroughbred Retirement Foundation at www.trfinc.org.

Family and friends may call from 5 to 7 p.m. on Tuesday, January 16, 2024 at Compassionate Funeral Care, 402 Maple Ave. (Rte 9 and/or Marion Ave.), Saratoga Springs, NY 12866.

A mass service will be held at 10 a.m. on Wednesday, January 17, 2024 at St. Peter’s Church, 241 Broadway, Saratoga Springs, NY 12866. 

In lieu of flowers, the family asks for donations to the Thoroughbred Retirement Foundation at www.trfinc.org.

Condolences may be shared at compassionatefuneralcare.com