Gary May, beloved Pop Warner football coach, passes away at the age of 69
By Cary Shuman
Gary May, one of the most influential and inspiring Chelsea Pop Warner coaches in the history of the city, died Monday, March 3, 2025, following a lengthy illness. He was 69.
Born on August 3, 1955, in Chelsea, Gary May was the son Ray and Fay May. He grew up on Grove Street and spent a lot of his childhood playing sports with his friends at nearby Bosson Park. He graduated from Shurtleff Junior High and Chelsea High School.
“My loved to tell people he was from Chelsea,” said his son, Gary May II.
Mr. May had a successful career in logistics, overseeing West Coast operations for Ames Color-File, a company based in Somerville, for 25 years.
The leader of The Junkyard Dogs
Throughout the 1980s, when Chelsea Pop Warner had more than 150 players in multiple divisions, Gary May was considered football coaching royalty. He affectionately nicknamed his teams, “The Junkyard Dogs.” His brother, Enos May, his nephew, Eric May, Larry Dulong, and Ray Deleidi were among the assistant coaches who served on his staff.
Gary May II, recalled the origin of Coach May’s “Junkyard Dogs.”
“My father started playing Queen’s Greatest Hits album and the Junkyard Dog was a famous wrestler at the time who used the song, “Another One Bites The Dust,” as his entrance music. My father would play that song after every game over the loudspeaker. Also, our family dog, Meeko, a White Samoyed Husky, used to work in the junkyard across the street from Borr’s Auto Parts, because May Security ran the overnight security there. So, the coaches called their football players The Junkyard Dogs, and Meeko became the team mascot.”
Mr. May also had a great sense of humor, according to his son, Gary May II. “My father would reward the kids after every win by loading up his Chevy S-10 with hundreds of bags of peanuts and each player could take home several pounds of peanuts home.”
“The kids loved him,” said Gary May II. “He was also a great father, so generous that he would literally give you the shirt off his back. My father never missed a Chelsea High football game in which I played. He never a Northeast Regional game in which my brothers (Danny, David and Kevin), played. Sometimes he had four kids playing baseball at the same time, from Little League to Pony League, and my father made sure to make every single game.”
Mr. May not only taught his football players the techniques of the sport, but he became a mentor and father-figure to his players.
Some of the standout players for Coach Gary May during that magical era of Pop Warner football included Gilberto Castro, Robert Yee, Michael Yee, Ernie Lombard, Gino Gillis, Mark Sujko, Luis Roman, Pedro Roman, Anthony Covino, and Ole Andrades.
Many credit Gary May for setting the foundation with his former Pop Warner players for the title-contending 1989 Chelsea High School team that advanced to the Commonwealth Conference championship game at Greater Lowell, falling one win short of a Super Bowl berth.
Mr. May also mentored one of Chelsea High School’s greatest players, Qasim Ward, a teammate of Mr. May’s son, Gary May II, on the 1995 Super Bowl champion Red Devils under the leadership of head coach Joe Gaff. The quarterback of that championship team was Stephen Turner, who benefited greatly from Mr. May’s support and advisership through the years.
A loyal fan of the Red Devils Mr. May felt at the time that running back Jadiem Brooks, who had graduated in June of 1995, was a true superstar. “My father and I had the same opinion: Jadiem Brooks was the greatest football player to run through Chelsea. And my father had watched Chelsea football for decades.”
A supportive family
Mr. May encountered health problems in his later years, but he battled them with the toughness and tenacity that he had instilled his sons and his football players during his amazing career as a youth coach.
One shining star who assisted Mr. May greatly during his medical situation over the last 10 years was daughter-in-law Jacqueline Caraballo.
“She accompanied him to his doctor’s appointments and was by his side through the last days of his life,” said Gary May II of Mr. May’s former daughter-in-law. “She provided excellent care for him.”
April May and her partner, James Jobes, assisted Mr. May with in-house care.
‘Dad, I love you’
Gary May II said he will deliver the eulogy at his father’s private memorial observance.
“I will a story of my favorite memory, which was my father, [grandson] Jackson, and I singing “Folsom Prison Blues” by Johnny Cash at Jackson’s graduation party on Webster Avenue,” said Gary May II. My best friend, Yoel, said it was the coolest thing he had ever seen.”
And Gary May II will express his love and admiration for his father in his speech: “Dad, I love you. I will love you forever.”
Mr. May leaves sons, Raymond May II of Billerica, Gary May II of Chelsea, Daniel O’Connor Jr. of Florida, David O’Connor of Revere, Kevin O’Connor and his wife, Melissa (Egan) O’Connor, of Hudson, N.H., and Stephen Turner of Clearwater, Fla. He was the brother of the late Enos May and his wife, Leatha May. He also leaves three grandchildren, Jackson May of Chelsea, Enos May of Lowell, and Makayla May of Saugus.
In lieu of flowers, donations may be made to any football program in the City of Chelsea.