Steve Hollingsworth ’84: The Heart of the Boston Red Sox

Steve Hollingsworth ’84:  The Heart of the Boston Red Sox

Even when Steve Hollingsworth was attending classes at Fairfield back in the 1980s he was daydreaming about what he would most love to do when he graduated college — become a baseball broadcaster.

Hollingsworth, who graduated in 1984 with a degree in marketing and a minor in communication, didn’t go on to call games on the radio or television. Instead he launched a successful career as a financial planner, helping manage individuals’ finances for when they retire. But a chance meeting allowed him to become personally involved with his favorite baseball team, the Boston Red Sox.

“Ten years ago, while on a trip to Chicago with my wife we sat across from the past BoSox (Club) president, Ed Keohane and his wife Joan,” said the now 52-year-old Hollingsworth, who lives in Wellesley, Mass. with his wife and their three boys, Nick, 13, Ryan, 9, and Brandon, 7. “We started talking to them over lunch in a cafe and he recruited me to become a member.”

The BoSox Club had its genesis with the Major League Baseball season of 1966, when the Red Sox lost 90 games and finished last in the American League. In 1967, the first year, the club signed up 305 members from around New England, and officers were elected.

Whether it was good fortune, good play, the hitting of Hall of Famer Carl Yastrzemski, the efforts of the newly-formed club, or all of the above, 1967 resulted in what is still known around New England and beyond as the “The Impossible Dream” season, one in which the Red Sox won 90 games and the American League pennant to make it to the World Series.
The Red Sox have had their ups and downs since that season, including winning three World Series in recent years, and the BoSox Club has continued to carry out its mission and grow in membership. The Club is recognized by the Red Sox as the “Official Booster Club of the Team” and contributes to a variety of charitable causes through a number of events and special programs. Mostly though, the BoSox Club continues to provide an intimate “behind the ropes” experience for its members through monthly luncheons, spring training trips, barbecues and more.

Hollingsworth spoke about his rise through the organization to become its president. “As president, I oversee the club’s board of directors and run the 10 to 12 events we have during the season, especially the spring training events. It is very rewarding to get to know all the passionate BoSox members, professional players and club executives of the Red Sox. But the most rewarding part of my job is to see how much we are able to give back to the Red Sox charities.”

While a Red Sox fan his entire life, Hollingsworth really notched up his interest and enthusiasm in the early 1990’s. “My fondest memory of Red Sox baseball was being able to attend almost every home and away playoff game during the 2013 season (that resulted in a Red Sox World Championship). It was truly a magical and surprising season for all Red Sox fans.”

He said his time at Fairfield and work with the BoSox Club goes hand in hand. “My Fairfield Jesuit education had always ingrained in me the importance of giving back and supporting humanitarian work. As the leader of a charity organization like the BoSox Club, I am able to help along with my fellow members improve the lives of others who are less fortunate. That is the most rewarding part of being the 25th BoSox Club president.”

There’s one other important byproduct of his involvement with the Club, the fantasy that floated through his mind while in class at Fairfield. “Being BoSox Club president lets me live out that dream I had of being a broadcaster, as I have the opportunity to interview Boston Red Sox players in front of our group of members all the time.”