Obituary for Thomas David Reilley Jr.

Thomas David Reilley Jr., 78, of Hilton Head Island, SC, passed away May 2, 2025, after facing his final challenge with the same courage and stubborn resolve that defined his life.

Tom, as he was known, was born April 12, 1947, in Providence, Rhode Island, to Vera Galassi Reilley and Thomas David Reilley Sr. He was one of eight siblings raised in a spirited Irish-Italian household, where the defining tradition was simple but profound: the door was always open.

At age 20, Tom enlisted in the United States Navy, where he served honorably as a Quartermaster Seaman aboard the USS Lafayette, a ballistic missile submarine from 1968 to 1971.

Following his honorable discharge from the Navy in 1971, Tom stepped into the food and beverage world—and never looked back. He began at Quidnessett Country Club in North Kingstown, then moved on to a dinner theater in Warwick, Rhode Island, called Chateau Deville. That job became unforgettable, as it was the place where he met the woman who would become his partner in all things, Diane.

In 1977, Tom and his wife Diane visited his sister Mary in Hilton Head Island and were quickly drawn in by the island’s charm and possibilities. They made Hilton Head their home later that year. Tom began as a banquet manager at the Hyatt and later worked as a food representative for American Foods, while Diane took a job at the Hofbräuhaus restaurant. When American Foods closed, with four children and a mortgage, Tom found himself at a crossroads. With help from Peter Kenneweg and Serg Pratt, he secured a loan and opened Reilley’s Grill & Bar in 1982. What began as a necessity became a legacy, growing into a family of restaurants and a family of his own who would proudly follow in his footsteps. Today, Coastal Restaurants and Bars is a partnership primarily between multiple generations of the Reilley and Kenneweg families that includes concepts founded by both generations, something Tom was very proud of.

There are countless stories—shared and unshared—that were born inside the walls of CRAB’s venues. One of the most unexpected and enduring came in the early days of the St. Francis by the Sea Catholic Church, when Tom opened the doors of The Crazy Crab to host Sunday Mass. For a time, it became known lovingly in the community as “The Holy Crab.”

In recognition of his service and contributions to the Catholic community, Tom received the Knights of Columbus Citizen of the Year Award in 1986.

Tom’s influence extended far beyond food. In 1983, he founded the Hilton Head Island St. Patrick’s Day Parade—South Carolina’s oldest and longest-running parade of its kind. What began as a modest neighborhood march grew into a beloved tradition, drawing over 40,000 attendees each year and earning recognition as one of the Top 20 Tourism Events in the Southeast. Tom proudly served as Grand Marshal in 1993, following in the footsteps of his father, who was honored in 1988. Tom’s wife, Diane, was selected to serve as Grand Marshal in the upcoming 40th annual Parade.

Also in 1983, Tom founded the Reilley’s Pro-Am—now the Reilley’s Match Play Championship—which has grown into Hilton Head Island’s second-largest golf tournament, drawing players from across the U.S., Canada, and Europe, and earning national recognition in Golf Digest and Golf World.

Due to both the economic and social impact brought in by both the parade and the tournament, in 2018, Tom was honored with the John Curry Tourism Award by the Hilton Head Island-Bluffton Chamber of Commerce, a recognition given to those whose dedication has fundamentally shaped the island’s tourism industry. In his acceptance speech, Tom said, “This is an honor and the best thing that has happened to me in a long time.” Chamber President Bill Miles called his hospitality “legendary” and praised his legacy as one built on “hard work, ingenuity, grit, and character.”

Tom proudly served as a trustee on the Heritage Classic Foundation Board and was the longtime chairman of the Heritage Classic Pro-Am. In 2023, he was honored as the RBC Heritage’s Honorary Chairman, as it was his final year on the board.

At the time of his passing, Tom was surrounded by his loving family—those who knew him as a devoted husband, father, brother, grandfather, and uncle. He will be forever remembered as the island’s warmest restaurateur, whose love radiated outward to family, friends, coworkers, customers, and even those just passing through. To know Tom was to feel welcomed, seen, and valued. He shared his wisdom freely, always encouraging others to grow—at work, in life, and in the quiet spaces in between.

His true legacy isn’t found in the restaurants, the parade, or the tournament he founded—but in the countless lives he touched with his humor, insight, compassion, and generosity. For Tom, generosity was his way of saying “I love you.”

Tom is survived by his wife of 47 years, Diane Reilley, and their seven children: Keith Reilley and his son Logan, Erin Reilley Booth, her husband, Jamie Booth, and their daughters, Jada (Matt) and Peyton, Brendan Reilley, his children Brendan Jr. (Ana), Taylor, Madison, and Aubrey, and his loving partner, Caroline Hamberg, Jeffrey Reilley, his wife, Lauren Reilley, and their children Jackson, Ansley, Addison, and Landon, Catherine Reilley and fiancé Todd Fox, Thomas Reilley, his loving partner, Whitney Wyatt, and their children Drake, Juliette, and Vera, and Tom’s youngest daughter Jenna Flynn. Tom is also survived by his siblings, Dennis Reilley (Deanna Lynn), Michaela Simmons (Kip), Pattie Culton (Bain), David Reilley (Laura), and Susan Reilley, along with many nieces and nephews. He was preceded in death by his parents, Thomas David Reilley Sr. and Vera Galassi Reilley, as well as his brother Michael Reilley (Marcia) and his sister Mary Rankin (Bill), whose daughters Reilley and Caroline spent life especially close with their Uncle Tom.

A funeral Mass will be held at Holy Family Catholic Church on Tuesday, May 13th, at 1:00 PM. In lieu of flowers, donations may be made to The Boys & Girls Club of Hilton Head in Tom’s honor.

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