Thomas O'Reilly, 89, with a life well-lived, passed away on Monday, November 24, surrounded by his family.
Tom was known for his love of his family, his outgoing personality, and his warmth and charm.

Born to Mary and Thomas O'Reilly in Philadelphia, Tom grew up in nearby Broomall with his younger twin siblings, Marianne and John. He spent childhood summers racing along the boardwalk in Atlantic City and his teenage years slipping into West Philadelphia jazz clubs to hear Dizzy Gillespie, John Coltrane, and other greats—nurturing a love of music that stayed with him for life.

After graduating high school in 1954, Tom entered Villanova University where, as he liked to joke, he "majored in pinochle." He soon left school and went to work as a salesman—peddling Gerber baby food, vacuums, and whatever else he could sell with his signature mix of humor and charm—before enlisting in the Army in 1957.

In 1962, while stationed at Fort Devens in Massachusetts, Tom met Lillian Leblanc. After only a few short weeks, and on Valentine's Day, he asked her to marry him. They wed on July 20, 1963, and welcomed their first son, Michael, the following year. Together, they would celebrate 60 Valentine's Days together before Lil's passing in 2022.

In 1967, the young family was posted to Japan on the northern island of Hokkaido. Their three years there were unforgettable. Tom and Lil embraced every opportunity to explore the island's natural beauty and culture, and the mementos they brought home decorated his home to this day. Their family also grew during this time, with sons Sean and Kevin arriving while they lived abroad.

After leaving military service, Tom and Lil settled in Maine in 1972, where their youngest child, Laurie, was soon born. Tom embarked on what became a long and respected second career in the tractor-trailer industry. He had a natural gift for connecting with people, and over the decades he built a reputation not just as a skilled salesman but as a trusted partner to customers across Maine and, later, the East Coast.
Never one to stop learning, Tom returned to school as an adult, attending classes at night while working full time and raising four children. He graduated from Westbrook College with top honors and received the President's Cup, an accomplishment he cherished.

In mid-life, Tom made another decision that shaped the rest of his years: He entered recovery and remained 36 years sober. His sobriety was a source of deep pride and gratitude, and he hoped that by sharing his story, he could help others on their own journeys to recovery.
While Tom was proud of his military service and professional achievements, he took greatest pride in his family. When his children were young, he devoted hours to volunteering as a coach and head umpire for the local Little League. His booming voice, fairness, and sense of humor made him unforgettable to a generation of neighborhood kids. He also served in many volunteer roles at St. Bartholomew Church as his kids grew up, including as heads of CCD and youth ministry, always eager to help guide young people with warmth and patience. He was also a member of the Knights of Columbus.
Tom rarely missed a soccer match, baseball game, track meet, or band concert, cheering on his children with enthusiasm and pride. And he joyfully carried on the tradition with his three grandchildren, spending hours perched on softball field bleachers or standing rinkside at ice arenas to support them.

As a retiree, Tom indulged his lifelong passion for golf (he even sank a hole-in-one in 1995), delighted in trips to Dairy Queen and IHOP with his grandkids, and often took to the road with Lil—whether for a Sunday drive, their annual leaf-peeping jaunt to New Hamphire, or for longer trips along the eastern seaboard, the strains of 50s doo-wop or old-style bluegrass drifting from the car windows. Their road trips took them from Niagara Falls to St. Augustine, Savannah to the Outer Banks, Myrtle Beach to Ocean City, among many other destinations.

When Lil's health declined, Tom cared for her with quiet dedication. His patience, steadiness, and commitment during those years reflected the depth of the love they shared across six decades. He never saw it as a burden—only as the natural extension of a lifetime of partnership.
Tom is survived by his three sons, Michael and his wife Joanne, Sean and his wife Carol, and Kevin and his wife Nancy; his daughter, Laurie; his three grandchildren, Madison, Jake, and Felicia; and his brother, John O'Reilly, along with numerous nieces and nephews.
Tom leaves his family with countless memories of laughter, guidance, and unconditional love. He will be deeply missed by all who knew him, and his family take comfort knowing he is at peace and reunited with Lil, the love of his life.

Visiting hours celebrating Tom's life will be held from 4:30 to 7 p.m. on Thursday, December 4, at Hobbs Funeral Home, 230 Cottage Street, South Portland. A funeral mass will be held at 10 a.m. on Friday, December 5, at St. Bartholomew Church, 8 Two Lights Road, Cape Elizabeth, followed by an interment ceremony at Calvary Cemetery, 1461 Broadway, South Portland. A reception will be held at Purpoodock Golf Club, 300 Spurwink Road, Cape Elizabeth.

In lieu of flowers, Tom's family asks that you consider a donation to Disabled Veterans of America (https://www.dav.org/).