19 years as a Littleton resident. 15 years building a youth program. Ready to serve our whole community.
James Kennedy and his family have called Littleton home since 2007. As a business owner, civic leader, and youth program director, James has spent nearly two decades investing in the people and places that make this town special.
James is the founder and president of Littleton Youth Wrestling — an official Park & Recreation program and 501(c)(3) non-profit — giving him a unique perspective as both an insider who understands how the department operates and an advocate who has seen firsthand what Littleton families need from their parks and recreation programs.
As a former member of the Lowell School Committee (1992–1994), business owner, and President of the Littleton Business Association for over 10 years, James brings real governance experience, financial discipline, and deep community connections to this race. He's not running to learn on the job — he's been doing this type of work for decades.
James grew up in Lowell, MA, where he compiled one of the most outstanding wrestling careers in the storied history of Lowell High School. His discipline and work ethic on the mat have defined his approach to everything he has done since — in business, in civic life, and in coaching Littleton's kids.
James Kennedy is one of the most decorated wrestlers in the history of Lowell High School. Referred to by legendary coach George Bossi as "one of the best I ever coached," Jim compiled an extraordinary four-year high school record and went on to achieve All-American status at the collegiate level.
As a senior in 1986–87, James finished the season undefeated — winning the Merrimack Valley Conference, North Sectional, Massachusetts State, and New England Championships at 141 lbs. He was named Wrestler of the Year by both the Boston Globe and the Boston Herald.
“One of the best I ever coached.”— George Bossi, Legendary Lowell High School Wrestling Coach
“Wrestling taught me that you don't get anything you don't earn. That's how I've approached everything — business, coaching, and now this campaign.”— James Kennedy
Ask any Littleton family about P&R programs and you'll hear the same thing: they matter. After nearly two decades running a youth program alongside this department, I know what's working — and where we can do more.
Preserving, expanding, and improving the programs Littleton families love is the top priority. A Youth Scholarship Fund exists to help qualifying families participate — and every dollar saved through smarter operations is a dollar that protects program quality and keeps fees manageable for everyone.
Littleton operates within roughly 70–80 spaces — but most are only accessible by phone, email, or PDF form during office hours. I'll work with P&R staff, the Select Board, and the IT department to make our facilities easier to find, request, and use. Starting with our $3.5M investment at 36 King Street.
As a program director for nearly two decades, I've seen how board-level decisions affect families on the ground. I'll make sure the community always has a clear voice in how P&R resources are allocated — and that every technology investment is implemented responsibly and transparently.
In 2009, James founded Littleton Youth Wrestling — "Tiger Wrestling" — as an official Park & Recreation program and 501(c)3 non-profit. Open to all boys and girls in grades K–8, the program has served hundreds of Littleton kids over 15 seasons.
James serves as founder, president, and head coach. The program practices at the Littleton Parks, Recreation and Community Education facility at 36 King Street, and competes as an official Massachusetts USA Wrestling club — giving Littleton kids access to local, regional, and national competition.
No wrestling experience is necessary. The program builds physical fitness, confidence, and sportsmanship — the same values James has carried throughout his own career.
Visit littletonwrestling.org →“I haven't just used Littleton's parks and recreation — I've helped build it from the inside for 15 years. Now I want to serve the whole community.”— James Kennedy
Local races are decided by small margins. A contribution to this campaign — any amount — helps reach more Littleton voters before Election Day.
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Committee to Elect James Kennedy
Littleton, MA 01460
Paid for by the Committee to Elect James Kennedy. Contributions are not tax deductible. This committee has filed its Statement of Organization with the Town of Littleton in accordance with Massachusetts campaign finance law.
Election Day is May 9, 2026. Every conversation, every shared post, and every vote makes a real difference in a local race like this.
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