By Joshua Boyd
Posted May. 14, 2016 at 8:52 PM IPSWICH
Bob Greenleaf still salutes and supports what the Intertown Twilight League provides for baseball players today, more than 10 years after his final games with the Ipswich Chiefs.To the 45-year-old Ipswich resident, the country’s oldest adult amateur league is an indispensable competitive outlet for players coming from so many different backgrounds.
“Throughout my time playing with the Chiefs [from 1988 through 2002], I played with college players from all divisions, and at least a dozen if not more who played professional baseball with Major League organizations,” said Greenleaf, who also was a coaching “mentor” from 2003 through 2005 for the Chiefs. Greenleaf was a player-coach from 1992 through 2002 for Ipswich’s ITL entry, taking over that job for the retiring legend Mike Singer.
On Saturday, Greenleaf – a multiple batting title winner in the ITL – joined Singer and other former Chiefs in the Intertown Twilight League Hall of Fame during its annual induction ceremony.
“It’s a really nice mix of players who made it very competitive. It also gives high school players a little higher level than they’re used to playing,” Greenleaf added, on the wide appeal of the ITL. “If you played high school and you don’t compete in college, or if you played in college and don’t go pro, you’re a competitor and you lose something if you don’t have that opportunity to compete.”
The ITL gave many players like Greenleaf, who played baseball for Ipswich High but switched to golf in college at North Carolina’s Catalba College. After his college athletic career was over, he knew he could always play golf, but also wanted to get back to his love of baseball.
With the ITL being so extremely competitive, Greenleaf remembers paying his dues during his first couple of years under Singer.
“Like in most leagues, you have to earn your stripes, and it took me a couple of years to steadily start playing for the team,” said Greenleaf.
In 1992, perhaps the most memorable conversation in his baseball life happened when Singer approached Greenleaf about taking over management of the Chiefs. “Because I loved the sport so much and wanted the team to continue, so I took on the responsibility as a player-coach for those years [1992-2002],” said Greenleaf, who currently works as a general manager with a commercial moving company out of Boston. During these times, not only was Greenleaf in charge of game-time decisions, but he also made impacts during the games. Along with a pair of batting titles, he also made the ITL All-Star team nine times. Those ITL All-Star teams would go on to play against All-Star teams from the Intercity League and North Shore Baseball League.
“Bob is a Chiefs icon,” said longtime Chief and later player-manager and manager Gardy O’Flynn. “He was such a steady player at third base for so many years, and he was instrumental in keeping the Chiefs going for over a decade.”
O’Flynn and Greenleaf were teammates in the early 1990s and later again in the 2000s as either teammates or as player (O’Flynn) and coach (Greenleaf). Joining other Chiefs staples like Ryan Montecalvo, David Shoreman, Andy Workman, Brad Eaton and others, they helped Ipswich win the 2003 ITL championship. It was Ipswich’s first since back-to-back titles in 1974 and 1975.
“For several years, Ipswich didn’t have a team that competed. We dedicated the championship to Mike Singer,” said Greenleaf. “He is the reason why the league is still where it is, through his love of the game. That was a huge accomplishment.”
Singer shocked Greenleaf a bit last year, when Singer invited Greenleaf and his wife Megan to join Singer and his wife at the Ipswich Athletic Hall of Fame induction ceremony. There, Singer was inducted primarily for his contributions to Ipswich High sports prior to his graduation in 1947. “He was certainly a mentor to me. I hadn’t seen Mike in a while, but he asked me and my wife to attend the Hall of Fame banquet with him,” said Greenleaf. “We enjoyed every part of it.”
Like Singer before him, Greenleaf hung up the cleats and glove, and just coached the team for three years, though he considers it more of a “mentor role” prior to handing over the reins of the team to Shoreman, Montecalvo and O’Flynn. “I played if the team needed me to play because of a lack of numbers in a game, but mostly I mentored Gardy, Ryan and Dav. Mostly, I just managed the team and made sure there was a team to play for within Ipswich,” said Greenleaf. Because the Chiefs, he feels, is important as part of the fabric of life in Ipswich. “As a baseball player, as someone who loves the game, the Chiefs are one of the most important things to a player in town,” he added. “The competition between the teams within the league is fantastic. The fun part is that you’re competing against seven different towns, and you make friendships.
“I can’t tell you how many times I’ve run into someone I played against from Rockport or Manchester or Beverly and the common theme is, ‘let’s get together for a beer,’” said Greenleaf. “It’s a nice bond throughout the years.”
Today, Greenleaf is the parent of an Ipswich High School student-athlete, his daughter Mackenzie. She was a member of the varsity swimming team this past winter and also was a member of the high school golf program last fall. Bob himself remains a competitive golf player, playing in many area golf tournaments. “I love the ability to compete, and it allows you to use what you’re born with, this fight and drive to win,” added Greenleaf. That fight and drive helped Greenleaf steer his favorite baseball team to the 2003 ITL title, and it has helped Greenleaf into the ITL Hall of Fame.
“It was really a pleasant surprise [when he heard about the HOF nomination],” said Greenleaf. “It’s really nice to be able to say you’re inducted into a Hall of Fame. The ITL is the oldest twilight baseball league in America, so I’m certainly proud to be inducted.”
