Richard Costello Helped Make The Squire A Chatham Icon

By: Tim Wood

Richard Costello. KIM RODERIQUES PHOTO

CHATHAM – For more than half a century, Richard Costello was the public face of The Chatham Squire, the iconic tavern in downtown Chatham. On most days, he could be found greeting customers and friends, making sure everyone was having a good time and the operation was running smoothly.

For most of those years he was also deeply involved in the community, sponsoring numerous events, including the popular Costume Caper Road Race on First Night, and serving as a selectman in the late 1980s.

Mr. Costello, 80, passed away Sunday after a short battle with cancer.

Mr. Costello opened The Squire with partner George Payne in 1968, converting the former New York Restaurant into a welcoming bar and restaurant. They choose the name based on the old English concept of the “squire” being at the center of a community.

“People would go to see the squire to get help, tell their tales of woe and just find out what was going on,” Mr. Costello said in a 2011 Chronicle profile. And, he added, “it was an easy name to remember.”

The duo made the funky, rambling building, whose core is an 1850s-era Greek Revival house, into a gathering spot for fishermen and executives alike, something Mr. Costello was proud of. Many patrons donated the license plates that decorate the main bar, and The Squire's annual Halloween party was notorious for the elaborate costumes of attendees. The restaurant became known for fresh seafood, including the cod cheeks that Mr. Costello discovered made for perfect fish and chips.

The Squire became one of Chatham's best-known exports. Tell anyone almost anywhere that you are from Chatham, and they'll tell you about the time they went to The Squire. Mr. Costello was passionate about the restaurant and was hands-on, while Payne was more of a quiet presence.

“They complemented each other,” said Richard Sullivan, The Squire's former manager who worked at the restaurant for 32 years. “That was really the formula for their success.”

While The Squire gained a reputation for its food and drink, it was the atmosphere Mr. Costello and Payne fostered among the staff that kept many customers coming back.

“It's a family,” Mimi van der Burg said in a 2018 story in The Chronicle about The Squire's 50th anniversary. “They take care of you when you're down and out. When you're happy, they're with you.”

“I really think he instilled a strong work ethic in all of us,” said Sullivan. Mr. Costello could be a tough boss, he said, and would sometimes come across as gruff because of his direct manner. “He didn't really mince words,” Sullivan said.

“But he really had a heart of gold,” he said. He wanted his staff to treat the customers well but also have fun, and would make unexpected kind gestures, such as having a masseuse come in or slipping some extra money to a worker about to go on vacation.

Mr. Costello was happy to share The Squire's success. He hosted an annual children's Christmas party, was an original sponsor of the Chatham Harbor Run, the First Night Carnival Caper and an old timers softball league team. He helped create the Pals for Life Foundation, which benefits hospitality industry workers. The Squire's familiar seagull logo often appeared on the sponsor list of Chatham events. For decades he gave out free Hoodsie ice cream during the town's Fourth of July parade; the only year he missed was when he was the parade grand marshal.

“He was very involved in charitable activities,” recalled William Litchfield, an attorney and the town moderator. “He was very, very generous. He did a lot in a quiet way.”

Mr. Costello served one year on the board of selectmen, winning election to the town's first part-time board in 1987. He also served on the town's public ceremonies committee and was very active in the town's business community. Until its sale in 2019, The Squire had been under continuous owners longer than any other restaurant in town, Litchfield said.

“Even after that, people tended to think of Richard” in connection with The Squire, he said. “He was so identified with it for so long.”

Born into a large Irish family in East Boston, Mr. Costello began cooking at an early age and worked in restaurants in Boston, building experience. He also took courses at Northeastern University's culinary school. He ran the kitchen at a bar and restaurant called the Branding Iron before purchasing The Squire with his friend George Payne. At first the restaurant was only open seasonally, but became a year-round operation in the late 1980s. No matter what the weather, it could always be counted on to be open, and its generator made it a welcome haven when storms knocked out power.

Mr. Costello always made sure the kitchen staff was taken care of, Sullivan said. Especially when it was busy in the summer, he'd give them words of encouragement or slip them a few beers. “He loved the kitchen people.”

Mr. Costello traveled extensively. In 2012 Mr. Costello was the top vote-getter online in the annual Ernest Hemingway look-alike contest sponsored by the Florida Keys Tourism Council, which flew him to Key West for the in-personal finals.

Mr. Costello was devoted to his wife Wendy, who passed away in 2007, and in fact died on her birthday, Sullivan said. Mr. Costello later met Ann Marie Doherty, who became his partner for his remaining years and who was by his side when he died.

When the restaurant was sold in May 2019, Mr. Costello said he enjoyed his years of ownership but “50-plus years are enough.”

“The good parts outweigh the bad,” he said.

Todd Hearle, who bought The Squire in 2019, called Mr. Costello “a great man.”

“He had brains, balls and a sense of humor that threw people off balance,” he said in an email. “He spoke a lot of truth in our dealings. He was loved by everyone and his legacy will live on forever within the walls of The Squire.”

Asked about The Squire's success in The Chronicle's 2011 profile, Mr. Costello said, “I don't do it alone. Surround yourself with stars and people who like people. And just be nice to everybody.”

A celebration of Mr. Costello's life will be held later. In lieu of flowers, donations in Mr. Costello's name may be made to the Pals for Life Foundation, 213 AP Newcomb Rd., Brewster, MA 02631.