FOR a while, it wasn’t clear whether Billy Gilroy was going to accumulate more restaurants or marriages. Until a few years ago, he was dead even, five apiece. But he opened Macao Trading Co. last November in TriBeCa (his sixth), and will open his newest, East Side Social Club, on 230 East 51st Street in Manhattan next month. And he has managed to stay married this, his fifth time, for three years now.
Robert Wright for The New York Times
FAMILY FEAST Billy Gilroy with Devon, 25, and Grace, 26. They will combine their know-how at their new restaurant, East Side Social Club in Manhattan.
“You would hope you get smarter as you get older,” said Mr. Gilroy, 53.
Looking back on it, he has come to see that the very thing that made him a successful Manhattan restaurateur probably made him very bad at marriage.
“My restaurants are meant to be romantic places where you forget your problems,” he said.
His Employees Only restaurant in the West Village is a replica of a 1920s speak-easy. The lounge at Macao is decorated like a Far East brothel. Both spots go until the wee small hours, 4 a.m., and are best known for exotic cocktails.
A 1994 New York magazine piece on the hot-hot restaurant scene (“There’s a Model in My Soup”) described Mr. Gilroy, then 37, as a major player, a Page 6 fixture, “looking dapper in his Panama hat,” posing with his live-in model girlfriend RaShelle Murri and scoring mega-points for hosting and Cindy Crawford during the first month his Match restaurant was open.
“People want to believe in the glamour, believe in the romance, forget their problems for a little while,” Mr. Gilroy said while a power saw buzzed and he walked a visitor around the construction at his newest place, which will look like a 1950s mafia social club. “It’s a lot of fun, a lot of superficiality. Everyone’s happy, then the next day you wake up and it’s real life.”
Mr. Gilroy bought into the very romance that he peddled. “I never married somebody I didn’t love,” he said. “But a year later — hopefully you got a year of happiness out of it — you sort of wake up, you’re just two people and there are surprises.”
Among the things he woke up to in the course of five marriages was three children. He acknowledges not being the best father. “It’s an industry riddled with pitfalls, working to 4 or 5 in the morning,” he said.
His two oldest lived with their mother a three-hour drive away in Connecticut. He would try to see them once a month, but on weekends, when they were free, restaurants are busiest. When Devon was 11 and Grace 12, they would ride the Peter Pan bus into the Port Authority and their dad would take them to work at Lucky Strike. It was worst during their teenage years. His son abused drugs and was kicked out of two schools. His daughter stopped talking to him for five years, until she was 19.
Now, as she’s introduced, to put herself in family context, Grace Gilroy, 26, explained, “My mother was the first wife.”
“Second, baby,” Mr. Gilroy said. “She was the second wife.”
Billy Gilroy is a high school dropout from Flushing, Queens, who worked his way up Manhattan’s night life, busing tables as a teenager at Broome Street Bar; bartending in his 20s at the Water Club; managing Nell’s; becoming, at 32, a partner in Lucky Strike; and then, in the ’90s, at his flamboyant peak, an owner of the Match restaurants (two in Manhattan, one in the Hamptons).
It wasn’t as flambé as it appeared to be. “I over-leveraged myself, not only financially but emotionally,” he said.
In 2001, he closed the Match restaurants. His fourth marriage broke up and, he said, he had to take custody of his third child, a 5-year-old daughter. For two years he lived off the money he made from selling the time that remained on the closed restaurants’ leases.
The man in the Panama hat became, of all things, a single stay-at-home dad. “I watched my savings drop,” he said.
But he also slowed down enough to notice that his two oldest shared his work ethic and a love for the restaurant biz.
At 19, Grace asked to live with him. This was expediency at first — she was starting at and wanted a free place nearby. She’d stopped talking to him when he had the daughter with his fourth wife.
“I was so angry,” she said, “seeing him start a new family.”
With her father rarely around, and her single mother working two jobs, Grace had to be a parent to her younger brother, Devon.
“We were still little kids,” Devon said, “and she’d order for me at restaurants.”
In time, her feelings toward her dad softened. “We built a relationship,” she said. “I was able to see that he was just a human being. It wasn’t easy for him, either.”
This, of course, sounds smoother in retrospect. “All three of us were in therapy,” Mr. Gilroy said. “Cost me $500 a week.”
He was impressed that as a full-time student Grace worked a 40-hour week at the Maritime Hotel’s restaurant. By 22, she was the manager.
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