Obituary of James F. "Jimmy" Leland

James F. Leland, formerly of Duxbury, Plymouth, and Falmouth, passed away on March 11, 2025, at the age of 74. Born in Indiana to James and Georgina Leland, James was the third of eight children. His family moved to Kentucky and Virginia before settling in Dorchester, where he graduated from Boston English High School.

James began his professional career selling plumbing and heating supplies to support himself while attending business school. His entrepreneurial spirit led him to a successful career in life and disability insurance, where he earned a reputation as a natural salesperson. Known for his confidence and ability to build lasting relationships, James focused on providing value and trust over quick sales. He worked for esteemed companies such as Aetna, MetLife, Guardian, and Commonwealth Equities, before founding his own business, JFL Brokerage, in the early 1990s. After 20 years of running his company, James returned to where it all started, working as a salesperson for Portland Group. His vast knowledge, experience, and engaging personality earned him the loyalty and affection of countless customers, whom he treated as friends.

James was a passionate golfer, dedicating himself to constant improvement and achieving scratch golfer status for many years. He was proud to have made two hole-in-ones and was a member of the Halifax Country Club for over two decades, where he was a Club Champion on several occasions. He also cherished introducing his sons to the game. His last round of golf was spent with his three sons, sharing laughs and memories. James’ infectious sense of humor and lighthearted spirit earned him the affectionate nickname “the kidder” among friends, and he had a unique gift for bringing joy to any situation.

James’ warmth, unwavering dedication to family, and ability to brighten the lives of those around him will be deeply missed by all who had the privilege of knowing him.

James is survived by his three sons: Brent and wife Emily of Wenham, Daryl and wife Jaclyn of Nashua, NH, and Craig of Seattle, WA.  He was the proud grandfather of Margaret, Benjamin, Addyson, Wesley, and Cooper. He was a cherished brother to Mary Nardone of SC, John Leland of Portsmouth, NH, Joseph Leland of Kingston, Shana Martensen of CA, Michael Leland of SC, the late Robert Leland, and Barbara Leland.  He was also survived by many nieces and nephews, and friends. 

Relatives and friends are respectfully invited to greet the family during the visiting hours on Friday, March 14 from 4 to 7pm at the Edward V. Sullivan Funeral Home, 43 Winn Street, Burlington, MA. Funeral from the Sullivan Funeral Home on Saturday, March 15 at 9am and will conclude with a Funeral Mass at St. Margaret Church in St. Veronica Parish, 111 Winn Street, Burlington at 10am. 

In lieu of flowers, donations may be made to Alzheimer's Association to support those affected by Korsafoff syndrome.