Obituary of Robert William Gay

Bob Gay


Robert William Gay, 74, a proud veteran of the US Army, passed away on May 29, 2022, after a short battle with cancer. Bob was born on June 8, 1947, and graduated from Searles High School in Gt. Barrington, Massachusetts.  After graduation, he entered the United States Army and completed two tours of duty in Vietnam.  He received the Bronze Star Medal for meritorious achievement in ground operation against hostile forces and he received three (3) Army Commendation Medals for outstanding achievement in connection with military operations against a hostile force.

Bob was a gifted athlete and a devoted sports fan.  His high school yearbook read, “The outlook wasn’t brilliant for the Searles High nine that day, ‘Til to the mound to save the game went Robert “Lefty” Gay.”  Bob always knew the Vegas odds on every major sporting event.  He loved horse racing and owned a racehorse named Dare-a-Bet in the 1970s.

Golf was a passion of Bob’s and he took to the links each spring, summer, and fall with his golfing buddies Paul O’Brien, Jpat Murphy, and Bill Gillooly.

Bob was an avid outdoorsman.  He loved fishing and in the winter months, he and his good friend, Rich Dupuis, spent countless hours hunting deer during the shotgun, archery, and black powder seasons.

Bob was a beloved grandfather.  He cared deeply for his granddaughters, Jordan, Hannah, and Sierra Wynn.  They went ice fishing together, shared holidays, and Bob was their biggest fan at their plays, sporting events, birthdays, and graduations.

Bob is survived by his family, David and Nancy Carpenter of Lenox; Jeffrey and Winona Carpenter of Ashley Falls; Gregory and Elizabeth Carpenter of Pittsfield; Charles and Susan Wynn of Groton, MA; and Deborah Owens of Pittsfield.  His family also includes Jeb Carpenter, Jasmine Carpenter and her children, Jaiden and Olivia; Joseph and Sherri Carpenter, and their children Nathan, Markus, and Paityn; and Zachary and Jamie Carpenter and their son, Callahan.

He is predeceased by his longtime friend and companion, Jane B. Carpenter, and his good friends, Steve Conte and Thomas Hitchcock.

A Celebration of Bob’s life is planned for Saturday, June 25, 2022.  For information, contact Susan Wynn via phone or text at 978-595-8117. Condolences may be made through

4 Responses to Obituary of Robert William Gay

  1. Will miss Bob. Played many rounds of golf with him

  2. Bob was always a pleasure to play golf with.
    He had many good stories, suggestions and comments.
    Too soon gone; will be missed.
    Rest in peace my friend.

  3. bob and i were like the two old guys in the balcony on the muppets. We logged a lot of hours in the woods behind the carpenter estate. I will miss you old friend. Rich Dupuis

  4. I am very sorry for your loss. Bob and I graduated from High School. I would sometimes meet him in the grocery store and we would have a good chat and he was always at our class reunions. He would always have a story about my late husband and we would have a good laugh. RIP Bob

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