Richard William Costello

November 24, 1940May 9, 2021

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. 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.


14 May

Funeral Mass

12:00 pm

Holy Redeemer Catholic Church

Chatham, MA


Richard William Costello

have a memory or condolence to add?

Duke Courtnell

June 15, 2021

So long King. Richard was the Squire & the Squire was Richard. George Payne is my life long friend & we worked together at the New York Restaurant before George & Richie bought it & turned it into a legend. I was the bartender on opening night. In the early years before the Squire took off, Willy Five & I worked the bar & Richie would feed us after closing. We called him “Uncle Grampy” & my kids still refer to him by that nickname. The good times over all the years are too numerous to count (& should not be repeated in detail). He was THE BEST. His personality filled the room wherever he went. He & Wendy used to go to New Orleans for music festivals. They would always look up my daughter Patten, who worked at a bar called Lucy’s. The staff got to know him. When he walked in it was “Uncle Grampy’s back!”. He would pull up a stool, buy a round & tell a few stories. He was not just the King at the Squire. Have fun over there on the Other Shore, my dear old friend. See you there some day.

Vernon Smith

June 14, 2021

Hello Ann Marie,
We're so very sorry over Richard's passing! I know you were his lifeline these past years. We hope you,re OK, and finding some measure of peace.
To the family; Our sincere condolences at the loss of somebody truly larger than life!
To George; Very sorry for your loss of a dear friend. While I can never fully forgive you guys for getting me involved in this damn business, I'm grateful for your years of friendship, and the opportunity to learn from you.
To Ann; thank you for sharing your time with us ! Every visit was special for us .
We say good bye with tears, laughter, and much fondness.
Vern, Missy, Katie & all your Fish House friends xoxo

Amy Fierro Tagliaferri

May 23, 2021

Richard, I will miss you so much. I already do. I attended Squire University for over 20 years and learned how to enjoy life by working hard, playing hard from you. I quote one of your "Costello-isms" every day. I will keep your spirit alive. The group of us who adore you can't help but gather and reminisce often, and risk that "one hand grenade who would get us all!" My bartending years, and my travels with you are cherished memories. Thank you so. Hugs and kisses, Amy

Maxim Grebenyuk

May 20, 2021

As a long time employee of The Squire, I shall bring only the best memories of Richard!!! He was a pleasure to work for, he always treated all of us respectfully, always happy to talk to us. Over the years, I felt his support and kindness for me. May he Rest in Peace. Thanks for everything, dear Richard, I shall always remember you!!!

Kevin Rice

May 16, 2021

Richard will be very missed at Payomet in Truro... and we'll give him a special shoutout in August when one of his favorite music artists, Marcia Ball, takes the stage!

Paul Pornbeck

May 14, 2021

Thank you Richard for all the great memories I will always cherish Chatham partly because of you. God bless you and see you on the other side❤

Sheila Gaynor

May 14, 2021

Chatham Squire early 70’s...oh, what a time it was...happy,hippy,
fishermen’s bar...Beatles,Stones,
Dylan on the jukebox
The staff - Mike Ryan,Willy 5,
Terry,Karen,Tina,Kay H,Candy,
Chickie,Frank,Sue,Billy W,Janie,
McGovern,Mike H,Wade Bros,
And then there was Richard -
part Irish pol,,sometimes court
jester and always King.Thanks Richard.You kept the light on for a lot of people for a lot of years.
You had a great run and made
everyone feel they were part of something special.

Maryellen Murphy

May 14, 2021

Sending condolences from the youngest Murphy working at The Squire, summertime 1976. I started out at the Wychmere Harbor Club in the giant dining area and it was disastrous. So I eventually got hired at the Squire working in the dining room and the bar area. That summer I earned and exceeded my college savings expectations. RIP Richard; thank you for all that you started in creating a place for good food, lots of hard work and plenty of fun to go around. Its been a while since I've traveled to Cape Cod, so a road trip is in order to see what happening in Chatham and The Squire. Keep on and Carry on at the Sqiure.

Suzanne Brock

May 14, 2021

I did not know Richard personally but I would like say thank you to the man he was in terms of his committment to the community and his consistent support of the League of Women Voters of Cape Cod. The Chatham Squire has been a supporter of ours for many years and that happened because of Richard. Reading his obituary allowed me a brief glimpse of his life and illustrated why so many will miss him going forward. The LWVCCA has been grateful and will always be thankful for his years of support.
In sorrow,
Suzanne Brock, President- League of Women Voters of Cape Cod

Jay [JP] Murphy

May 14, 2021

Richard, I always loved listening to you and being around you. Thank you for the incredible times spent working at the Squire and all the friends gathered there. My sister Buffy introduced us in 1970 and I stayed working summers at the Squire until 1975. Some of the best and happiest times in my life aside from my 2 children, Patrick and Nell, and now my first grandchild born and named after me 'Jay'. There are just so many stories to tell from the early days at the Squire...some cannot even be retold. One of the times though we were on a boat, I think Otto was taking us to Nantucket for a big party and clam 5am we're sitting in the harbor with the fog thick as can we all just partied right there on the boat and never made it to Nantucket that time. I loved meeting up with you with my son Patrick at the 25th Anniversary...but now I'm living in Tampa Florida and couldn't make it to the others. My sisters Buffy and Emmy and I always laugh and talk about the days we all worked at the Squire. I miss those days of laughter and pure joy and living on the Cape. Rest in Peace Richard. Loved you like a brother. JayP Murphy, Bartender at the Squire 1970-1975ish also known as "Murph" at the bar.