Cape Cod League: Tom and Sheri Gay, Mainstays with the Wareham Gatemen

Sheri Gay and Tom Gay, postseason 2025. (Courtesy of Sheri and Tom Gay)

 

The Cape Cod Baseball League has a long history. With the exception of 1940 through 1946, when the league was curtailed by World War II, and 2020, when baseball was halted by the pandemic, the league has provided a team each summer since 1923 for a player to enjoy his love of the game.

For a league and a team to be formed and to exist, volunteers are needed. There have been hundreds, if not thousands, of volunteers who share their time, talent, and treasure to make the players, teams, and Cape League successes. The volunteers work throughout the year to make the seven-week season happen.

Each team has its volunteers. There are volunteers who have just begun to offer service to a team and to the league. Some may have a season or even less experience, while others have offered service to a team and the league for decades. Two people who have served the Wareham Gatemen and the league for years are Tom and Sheri Gay.

Tom and his six siblings were raised by Peter and Laura Gay in Taunton, Massachusetts. During summers, Peter and Laura had to find a way to occupy their children so they purchased a home at Onset, a village in the town of Wareham, Massachusetts. The family had been visiting Wareham during the summer for years. When Tom and Sheri were married, they continued the summer visits. The larger Gay family has been coming to Wareham for 70 years. Tom and Sheri enjoyed the area and purchased a home in the neighboring town of Marion, Massachusetts, where they have lived for the past 40 years.

Tom and Sheri are parents of Thomas Jr. and Lindsey. The children played Little League and Babe Ruth baseball, while Lindsey also played high-school baseball for Old Rochester Regional High School in Mattapoisett, Massachusetts. During a summer, the Gays attended a few games of the Wareham Gatemen. They learned of the baseball skills clinics hosted by the team as their children participated in the clinics run by the players. “The players were such role models,” said Sheri.

Tom and Sheri heard about the need for the players to have a home to live at as they played in the league. “We began to host players in 1997,” Tom said. “We have hosted close to 20 players.” Some seasons the Gays hosted only one player, while on occasion they hosted as many as three in one summer. “The players became part of our family,” said Tom. “We’ve attended a number of weddings of our players and have visited the players at their homes to meet their families.”

Tom has been involved with the team beyond hosting players. He became assistant general manager of the Gatemen after longtime GM John Wylde stepped down for health reasons. Wylde had been the general manager for 25 years. Tom became general manager in 2008 and added president to his title, holding both positions from 2009 to 2014. Then he became president of the Gatemen from 2014 to 2021 and was named senior vice president of the Cape Cod Baseball League since 2018.

 

Sheri Gay and Tom Gay behind Gatemen logo sign in July 2016. (Courtesy of Sheri and Tom Gay)

 

Sheri enjoys the Gatemen and the league. “The lure of the league is enticing once someone becomes involved,” she said. For her, the best part of the league is meeting people. “John Wylde, Judy Scarafile, Chuck Sturtevant, Andrew Lang, and Paul Gallop are and were great people,” she said of the many league representatives and administrators she has worked with over the years. “We have met players from across the country, their families, and we help the players to achieve their goals and their dreams,” she said. “We have made lifelong friends. I’m getting the chills remembering all of these people.”

She also mentioned Ben Crockett, senior vice president of baseball operations for the Boston Red Sox, and Jeremy Sowers, manager of major-league operations for the Tampa Bay Rays, who were involved with the Wareham franchise at one point.

When asked what makes the Cape Cod Baseball League special, Sheri answered, “I know it is the best summer baseball league in the United States. The league officers believe strongly in the league and want to give the players exposure to major-league scouts.”

“The teams play near one another, so scouts can see two or three games a day,” she continued. “We make the players feel at home and we want them to be better players when they leave the Cape. We also hold the players responsible for their behavior with their host families. The league also works hard to get the fans to cheer the players.”

Tom and Sheri’s long involvement with the league also gives them a perspective of it. “The league has its challenges,” said Tom. “The league is in a better place now than it was 10 years ago. Everyone across the country knows of the Cape Cod Baseball League.”

Tom noted the current issues with the NCAA and the portal that has caused problems throughout the league. “Say there is a player who is bringing in money and using the portal, the player can go from one team to another team. They can even go home,” he said. “If there is money involved and a player gets that money, why come to our league? The player’s advisers will tell them to stay home. Don’t go to the Cape.”

Tom focused on the positive aspect of what the Cape Cod League gives to a player. “At every game, the batters are facing great pitching. We help the players take their skills to the next level. We help them to learn what it takes to move to the next level,” Tom said, adding that host families play a pivotal role in the continued success of the league. “We always need beds for our players.”

Another challenge for the league is noticing how to keep a player in the league. “The league needs to move with the times,” said Tom. “In 2000 a Cape League coach would develop a relationship with a college baseball coach. A telephone call would be made to get a certain player to play for Wareham and there would be 20 players and five roster moves. Now the roster has 30 players. Players come and go. By the end of the season, half of the roster will have changed. These roster moves put a strain on beds and housing.”

There has been conversation about expansion of the league. Mashpee, New Bedford, and Plymouth have approached the league to add a team to the league. Expansion is difficult. “The league is used to 10 teams and 10 teams are good financially today,” Tom said. “With expansion, there would be a strain on finances and housing. With the Gatemen staff, we know where the beds are located. We know who the sponsors are. If a team is added, the team could ask sponsors and housing hosts to support the new team and possibly take these from the existing team.”

Tom believes the Cape Cod Baseball League is the best collegiate league in summer baseball. “Every person involved in the league before my time did a great job in building the league, in organizing the league. They made smart moves.”

In 1963, the league went from town teams to college teams and built the organization to attract the best college players. Today 15 to 25 players are drafted by Major League Baseball as first-round draft picks. There were over 400 players on major-league rosters in the 2025 season.

Tom shared a story about his time with the league concerning Toronto outfielder George Springer when he was with the University of Connecticut and played for Wareham in 2009 and 2010.

“In his first year, he had to make up school work and took a class at Bridgewater State University, but the University of Connecticut would not recognize the class,” Tom explained. “So, George’s grandfather would pick him up at 5:00 A.M. and drive him to Storrs, Connecticut, where he would attend class and then drive him back to the Cape for the daily game. That summer, George really grew at the Cape.”

Tom is pleased with the progress the Wareham Gatemen team has made during his current tenure. “There are new lights being installed for the 2026 season. Spillane Field has been renovated with town and team collaboration and the playing field and seating areas have been improved,” he said. “Younger people are involved and they are moving the team forward. They are doing a fabulous job.”

STEPHEN A. TRIMBLE has followed baseball for many years. He first joined SABR in 1981. In addition to following baseball, he enjoys serving as a Scout leader, exploring family history, listening to classical music, playing the piano, reading and collecting books, and playing Strat-O-Matic Baseball. He pastors First Baptist Church of North Attleborough, Massachusetts, where Bernie Carbo gave his faith testimony. He also works as a realtor on Cape Cod.

 

SOURCES

The author interviewed Tom and Sheri Gay on November 24, 2025, and on January 2, 2026.