James Carlisle MacLeod of Stuart, Florida and Boothbay, Maine, and formerly of Kent, Connecticut, passed away Nov. 24, 2023, at the age of 76, at Treasure Coast Hospice in Stuart, Florida, with his wife by his side, following a brief illness.

Jim was born in Gardiner, Maine on April 10, 1947, and was the son of the late Virginia Carlisle of Boothbay Harbor, Maine and Ronald F. MacLeod of Augusta, Maine. He is survived by his wife Carolyn Immordino MacLeod of 49 years; daughter Carrie S. MacLeod of Portland, Maine; daughter Jaime M. Berhanu and her husband Andy of Bowdoinham, Maine; and four grandchildren: Iyana Berhanu and Makeda Berhanu of Bowdoinham, Maine and Aviva Feinberg and Mayim Feinberg of Portland, Maine.

As a lifelong educator, Jim cherished the opportunity to connect with students. For 36 years, Jim was a dedicated and beloved faculty member at the Kent School in Kent, CT. During those years he served as a math teacher; student advisor; dean of students; football, basketball, and baseball coach; the Culture and Diversity Club advisor; and the school’s chess club faculty leader. Jim was the holder of the Kent School’s Independence Foundation Teaching Chair. For 25 years, Jim was the Kent School Boys varsity tennis coach. He took great pride in coaching his student-athletes. Jim also taught math and coached at the Hun School in Princeton, New Jersey for nine years before taking his position at the Kent School in 1982. He retired from Kent School in 2018.

Jim attended high school at the Deveaux School in Niagara Falls, New York, and the Nichols School in Buffalo, New York, before his family moved to Princeton, NJ. He graduated in 1966 from the Hun School in Princeton, NJ. He played football, basketball, and baseball at the varsity level at each prep school he attended. Jim graduated from the University of Delaware in 1970 with a BS in economics and earned an MAT degree in 1975 from Trenton State College (now known as The College of New Jersey).

Jim was a competitive and accomplished tennis player who competed in USTA tournaments from Maine to Florida from his mid-40s to his early 60s. He loved playing and watching basketball, and even after he stopped playing, he never lost interest in a good pickup game. He loved being on the water wherever he was, and could often be found windsurfing, kayaking, sailing, canoeing, floating, and swimming. Jim was passionate about chess and kept active in both local games and in the online chess community until his death. Before retiring in 2018, he hosted the Kent School Chess Club students at his home on the Kent School campus every Friday night where 20 or more students would gather in his living room and dining room to play chess and enjoy pizza.

Throughout his life, Jim found deep enjoyment in many life-enriching pastimes. He enjoyed playing the keyboard/piano, painting with acrylics and oil paint, listening to music (especially Queen), camping, biking, attending musical theater and concerts, and golfing. He especially loved spending time with his wife, daughters, and grandchildren at his beloved family home on Knickerbocker Lake in Boothbay, Maine, where he spent each summer of his life. Jim’s grandchildren brought him great joy and he was very proud to be their grandfather.

Jim served as president of the Knickerbocker Lake Association, Boothbay, Maine for 10 years. Jim also treasured a lifetime of companionship with his dogs, Dukie Darling, Knicky, Kelly and Casey, Firecracker, and Huey, and with his beloved Mama Cat.

Jim’s ability to connect with people endeared him to many. His sense of humor, easygoing manner, and friendly outlook allowed him to meet new friends wherever he traveled.

Jim is also survived by his brother Ronald MacLeod and wife Karen of Woodbridge, Virginia; his sister Mary Alice Brown and husband Dennis of Villa Rica, Georgia; cousins Jill Cummings of Stuart, Florida; David Rand and wife Julie of Jefferson, Maine; best friend Craig Stretch and wife Missi of Penn Valley, Pennsylvania; six nieces and nephews; many cousins from the Immordino/Bilancio family, and many dear friends, near and far.

Jim was one-of-a-kind, and he will be missed.

A memorial service will be held in the summer of 2024 in Maine at the family’s convenience.

In lieu of flowers, the family asks that donations in Jim’s name be sent to National Junior Tennis and Learning of Trenton (NJTLT), which shares the passion that Jim had for enriching the lives of youngsters through tennis, education, mentoring, and preparation for higher education: NJTL is a 501(c)3 non-profit so all donations are 100% tax-deductible. Donate online at https://www.njtloftrenton.org/donate-today or to their address at NJTL 949 W. State St, Trenton, NJ 08618.

Written remembrances can be submitted to  https://www.allcounty.com/obituaries/James-Carlisle-Macleod?obId=30000127