Remembering Tom Reilley: Father, husband, and the face of a Hilton Head restaurant empire

Yahoo

11-05-2025

It's almost five o'clock at Reilley's Grill and Bar on Hilton Head Island, and the long mahogany bar is already filled with silver-haired patrons enjoying a happy hour drink. Most of the tables in the restaurant are unusually empty; the rain is coming down hard outside, keeping most of the usual crowd of locals at home. But there's one more person missing from the scene who will never take his usual spot at the corner of the bar again.
Thomas Reilley, iconic Hilton Head restauranteur best known for founding Coastal Restaurants and Bars, passed away on May 2, after battling severe health problems for nearly three months. He celebrated his 78th birthday in the hospital in April.
His death marks the third loss of a major personality for the island this year — entrepreneurs and leaders in the food, beverage and hospitality industry who left their marks on locals' hearts through the connections they made.
The story of Reilley's Grill and Bar is a classic tale of Hilton Head Island: a young couple leaves behind their snowy hometowns in search of opportunity on a small island on the onset of becoming one of the biggest tourist destinations on the Atlantic coast. The Reilley family came to be more than the owners of a couple of successful restaurants — like others who established roots on the island in the early days, Tom's legacy is woven deep into the fabric of the town's history.
Tom was born in Providence, Rhode Island to an Irish father and an Italian mother. The oldest of eight siblings in a family that didn't have much money, Tom took on leadership and responsibility at a young age. He was protective of his younger siblings — taking his sisters to school dances when no one else could, keeping a close eye on who they were getting into cars with.
The future entrepreneur worked nearly all his life, starting out at his grandfather's marble and tile company from the age of 12 or 13. He spent years climbing the ladder in the food and beverage industry, often hiring his siblings to work underneath him. Tom's father, a realtor who at one time also owned a bar, passed down a valuable piece of wisdom to his children:
''Don't ever work like an employee,'' sister Michaela Simmons recalls her father saying. ''Work like an owner.''
Their family moved to Warwick, Rhode Island, when Tom's sister Patti Culton was a young girl. She recounted fond memories of playing with the neighborhood kids during the daytime but coming home when the street lights came on. Every evening, the whole family would come together for dinner and talk about what happened during the day and who said what to whom.
'Our whole childhood revolved around the kitchen table,' Culton said.
When Tom opened his first restaurant, his father told him to treat the restaurant 'like the kitchen table.' And he did, his sister said, carrying on the tradition of making people feel seen and heard and valued the moment they walked in the door.
'All I could think of when he passed away was that feeling like somebody had shut the kitchen lights off,' Culton said.
One evening in February 1977, Tom hopped in his Ford Torino and picked up his now-wife Diane, who thought he was taking her to go see the recently released film Rocky. Instead, he changed the course of their lives.
'He got on 95 the other way,' Diane recalled. 'I said, 'Where the heck are you going?' He said, 'South Carolina.''
They made the 18-hour journey from Boston down to Hilton Head Island, a place that had one traffic light and no big grocery store, and ended up staying. In the start, they lived with Tom's sisters Mary and her husband. Diane picked up at job at the the Calibogue Seafood House in Harbour Town, in a building that now houses the Crazy Crab; Tom started off at the Hyatt Regency as a manager in the banquet department.
It would be a few years before Tom and Diane got the opportunity to open their first restaurant: the original Reilley's, established in 1982. That building no longer exists; a fire in 1995 prompted the family to move the current location across the street, and the restaurant was remodeled in 2004. But the spirit of the Reilley's stayed the same: a place where Tom knew everybody's name and treated customers like family.
'Like Cheers,' Diane said.
Life with seven children got chaotic at time. The Reilley kids spent their youth running wild around a version of Hilton Head Island that's much different than the world their children will grow up in, a world where everybody knew everybody and neighbors watched over each others' kids. They'd run in and out of the nearby shops and restaurants: a boutique clothing store called The Porcupine, Curry Dry Cleaners, and restaurant down the road called Julep's, none of which are still standing on the island.
Tom was a man of routine up into his final years. Every morning at nine o'clock, he'd walk in to the restaurant to count the money from the night before, watching golf on the TV and chatting about with restaurant manager Kiel Phillips as he opened the bar. He had lunch every day with his son Jeff, and popped in for happy hour every evening to greet the regulars and enjoy his favorite drink: a glass of red wine over ice.
He worked seven days a week, and practically lived in his office. Back in the old days, his office was crammed into a small, nondescript room not much bigger than a storage closet. At five o'clock, he'd walk next door to what was called 'the boardroom' — a private, a dimly lit 'guy's club' where Tom and his buddies played darts and gin rummy. Kids weren't allowed, but sometimes son Thomas would steal a key and sneak in with his friends.
That's how things were until 2011. 'Then the group of guys just got a little small,' the son remarked. He and his brother Brendan transformed the place into a bar and music venue, and Tom moved to a nearby office in the same plaza.
As Tom got older, adult children began to take over the family company. Brendan has been the key driver in the company's growth in recent years, and has opened new restaurants with his brothers Thomas and Keith. His oldest daughter Erin Booth, who worked with him for 26 years, is now managing partner of Reilley's Grill and Bar along with her husband Jaime Booth. Catherine joined the group in 2021 after burning out from a long career worked in marketing for firms in New York, Chicago, and Boston. Jeff works as a real estate attorney, but owns a minority stake in some of the family's restaurants. 'Free-spirited' Jenna, the youngest of the bunch, is the only one not involved in the business, and lives in Colorado.
Tom's family extended beyond his seven children, son Thomas remarked.
The doors of the Reilley family home were always open. The kids' friends would come in and out, frequently spending the night. It wasn't uncommon for there to be twenty extra people in the house on the weekend. Tom and Diane also took in a handful of people not just friends and family, but anyone who needed a safe space to call home. Two of Tom's 'adopted' children were there by his bedside when he passed away.
One Monday morning in early February, Tom drove himself to Reilley's after going to a regular doctor's appointment, where he was told he had an irregular heartbeat. As he tallied the receipts like he did every morning, Tom started to feel very unwell.
Erin, who has worked alongside her father for 26 years, remembers sitting in her office when Tom called her to drive her home. She and her husband Jaime took him home and returned to the office to carry on with work. Less than 30 minutes after, Erin got another call from Tom.
'He said, 'I think I need to go to the hospital,'' said Erin.
An ambulance took Tom to Hilton Head Medical. Tom's wife Diane was in Jamaica at the time on a missionary trip. When she got back, she and Erin drove two hours north to the Medical University of South Carolina, where he stayed for two months.
He never really got better.
Tom's family made the difficult decision to transfer him to hospice care, after watching him battle his illnesses for nearly three months. He died surrounded by his wife, children, grandchildren, siblings, and cousins.
Most of Tom's family members were able to hold back tears as they spoke about the father, husband, or brother that they loved and admired so deeply. Erin, Tom's oldest daughter, broke down in tears almost immediately when asked to recall the man who was not just her father, but also her best friend.
'He had so much wisdom,' Erin said tearfully. 'He cared deeply. He really loved everybody and saw the positive in everybody ... I always knew that he was somebody that I could come to and I could rely on.'
The walls of Tom's office are coated in dozens of framed photographs and memorabilia. Sitting at his desk, Tom would have been surrounded by memories of weddings, family vacations, beach photo shoots, brothers and sisters, children and grandchildren all smiling from the walls. Taped to the left side of his computer monitor, alongside scribbled notes and reminders, is a printed photograph Erin and her husband Jamie.
The future of Coastal Restaurants and Bars is now in the hands of the surviving Reilley children, who admit they're not quite as outgoing as their father was. His personality, showmanship, and the ease at which he was able to connect with people made him a foundational piece of the restaurant empire that the family will never be able to replace.
'You don't have to know who owns Benny's,' son Thomas remarked, referring one of the family's more recent business ventures. 'Reilley's survived because Tom Reilley was there, and thrived.'
A funeral service for Thomas Reilley is schedule for May 13 at 1:00 p.m., at the Holy Family Catholic Church at 24 Pope Ave.