Richard William Costello

Richard W. Costello lost his short battle with cancer on May 9, 2021 at his home with his faithful companion Ann Marie by his side. He was surrounded with love all his days, and if possible more so in his final days. Their home welcomed family and friends during his illness often sharing stories (of which there are many), good food, moral support and love, lots of love. Richard had a huge family. He was born on November 24, 1940 in East Boston to a loving Irish family to parents Mary Margaret (Rymill) and Michael Costello, but he eventually built another family in Chatham when he opened the Chatham Squire in 1968 with his friend George Payne. He was a mentor, a teacher, a friend and occasionally a tormentor to all of them. They learned lifelong lessons from him that will be passed on to the next generation and the one after that. He was legendary then and will be forever.

He loved being the center of attention; he basked in it. His Squire family called him “The King” and he loved that. He embraced the town of Chatham and created a safe haven for the working class and the elite alike in the Squire. Where else could you see a polo shirt-clad preppie enjoying a beer with a fisherman fresh off the boat? He recycled and repurposed before it was a trend. When he saw uneaten food scraped into the garbage, he came up with the idea of getting pigs. Those pigs were well fed! Another example is when he discovered cod cheeks and tongues; he heard the fishermen were throwing the codfish heads away or squirreling them away for their own consumption, he made a deal. Bring him the cheeks and tongues (cheeks as you know are the perfect fish and chip, and tongues gave a rich flavor to the chowder) to the kitchen back door, and turn in a slip at the bar for cash. Anyone who worked for him knew to be conscious of waste, and not just food but not to waste time, energy and of course good times with your friends.

He taught how to give back by example too. He served on the Chatham board of selectmen, and gave back to the town in so many diverse ways. On any Chatham event, the Chatham Squire was listed as a sponsor; he hosted an annual children’s party with Santa in December with a gift for every child (bought from the Mayflower Shop), was an original and continuing sponsor of the Chatham Harbor Run, sponsored the Carnival Caper kick-off event for First Night and backed an old-timer’s softball team. He loved the 4th of July and Halloween. The only year he didn’t give out Hoodsies on the 4th was when he was the Grand Marshal, and the Squire’s Halloween Party was infamous. The Squire stayed open year round serving lunch and dinner even when it wasn’t profitable. They did it for the town. Hurricane? Nor’Easter? The Squire’s lights were on.

He eventually found financial success from the Squire but he didn’t spend it on a lavish house or car; he bought experiences. He won an online Hemingway look-alike contest in 2012. He travelled making lifelong friends along the way, he helped others financially without a question asked, and he helped create the Pals For Life Foundation to help anyone in the hospitality industry. If everyone gathered together who he helped both financially and emotionally, you might need to rent his beloved Fenway Park to fit them all. He loved the Splendid Splinter, and celebrated his birthday every year.

When he lost his beloved wife Wendy Costello in 2007, family and friends mourned with him. He met Ann Marie Doherty, and while they shared the experience of losing their beloved spouses, they were blessed to be able to share many years together while laughing and living life to the fullest. God bless Ann Marie. Her love and loyal care-giving was a gift his family and friends cherish. His brother Bobby described her as an angel on earth.

He is survived by his loving companion Ann Marie Doherty, his brother Bob Costello and wife Laurel, his sister Margaret (Peggy) Coppola; nieces, Laurene Visco-Grzybala, Karen St. Clair, Patti Biggs, Kathie Eagle, Barbara Compton, Michelle Gordy, Tracy Schwartz, Susan Costello, Colleen Kudrikow, and nephews John Visco, Salvatore Indorato, Rick Coppola, Chris Coppola, Michael Costello, Bobby Costello, many great-nieces and great-nephews, his dear friend George J.H. Payne, brother-in-law Michael Wade, Midnight the cat and too many special friends to name here. He was predeceased by his wife of 20 years Wendy Wade Costello, siblings Michael Costello, Lorraine Indorato and Mary Josephine Visco; brothers-in-law Sal Indorato, Buddy Coppola and John Visco, and close friend Pete Shelley. In lieu of flowers the family has requested donations be made to the Pals For Life Foundation, 213 AP Newcomb Rd. Brewster, Ma. 02631. www.palsforlife.com Richard would like that. A celebration of his life will be announced later.

“The people you love become ghosts inside of you and like this you keep them alive.” –Robert Burns.

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