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A Field of Dreams and Summer Saturdays

A Field of Dreams and Summer Saturdays

Jeff Wight’s involvement with Cayman Islands Little League spans about every imaginable role.

He played baseball and softball as a child and played in the co-ed league as an adult. He has coached, volunteered, worked as league commissioner and ultimately was inspired to pursue a master’s degree in sports business management thanks to his experiences playing as a kid.

“I can’t say enough about the programme and what it has done for me,” said Wight, who in addition to being a senior property manager with Dart, now serves on the YMCA Cayman Islands board.

These are the types of stories shared by thousands of children who have passed through the Cayman Islands Little League over the last three decades. They’re also the inspiration for a CI$2.7 million renovation project at the Field of Dreams that organisers hope will keep these success stories coming for decades to come.


J.C. Calhoun began organising what was to become the Cayman Islands Little League in 1989 and the first games — limited to youth co-ed softball — were played the next year on the George Hicks Middle School field.

“J.C., his whole big thing was, ‘It’s about way more than ball skills and winning,’” said long-time volunteer Sara Mackay, who now sits on the YMCA board. “It’s about [building] character.”

There was no fee for the players — which was a tradition that continued until this year, when a $100 fee was introduced — providing the opportunity for anyone to play, regardless of background.

“Race and social status didn’t really matter,” said Wight. “You’d be playing with a CEO’s kid and maybe [the child of] an hourly worker from a restaurant. Everybody was integrated perfectly.”

Little League Association President John Cridland said the inclusive nature of the programme made it unique. He recalled a team he coached on which there were children from various schools across various districts on the island.

“There’s nowhere else [in Cayman's children's sports scene] that you bring that dynamic together.”

Once it began, the league quickly grew and outgrew the field. Between 1996 and 1997, the Cayman Islands Little League acquired roughly 17 acres of land off Walkers Road in George Town and built what is now known as the Field of Dreams.

“The stands were always full and people cheering and going crazy,” Wight said, recalling the games he played at the Field of Dreams as a child. “Summer Saturdays were consumed from morning straight through until the evening with baseball and softball.”

Over time from so much use, the turf fields wore down. The Field of Dreams needed upgrading, but the core group of Little League volunteers were stretched thin.


YMCA in the Cayman Islands was established in 2012 with the mission of inspiring youth and strengthening the community. What it didn’t have, however, was a facility to call home.

Soon, leaders from both organisations saw the potential for partnership and in 2018 the YMCA signed on to operate the programmes and facilities at the Field of Dreams, which included its camps and programmes in addition to baseball and softball.

“What attracted us to Little League and helped it work was the league really had great facilities,” said YMCA Board Chairman David Watler. “And it had a really good, strong volunteer base.”


There’s arguably no better example of how the partnership between the YMCA and the Little League benefits Cayman than the recent renovations at the complex.

Little League originally planned a $1 million upgrade that would have addressed the turf, but with the YMCA’s vision, those plans were scrapped in favour of a $2.7 million renovation that is not a short-term fix, but a long-term investment. The new plans included upgrades to the facility’s lighting, fencing, parking lot, canteen, clubhouse, play area and more.

Dart recently announced a $350,000 sponsorship over 10 years to help fund the field improvements.

Meanwhile, the YMCA is surveying community members to learn what’s most needed from them and the complex.

“We need programmes and facilities and venues for the community to come together,” Watler said.

That includes the possibility of the YMCA — which has operated as a “Y without walls” up to this point — building its home at the complex as well.

That’s music to the ears of Wight, who now enjoys time at the fields in the stands as his sons follow in his footsteps.
“The vibe is coming back. That vibe of, ‘Wow. Little League is the place to be,'" Wight said. "It's happening and I'm still a huge advocate.”

This article appears in the February 2022 print edition of Camana Bay Times.

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