James (Jim) Michael Shields, Jr. of Hyannis, Massachusetts, affectionately called Jimmy, by family and friends, passed away, March 23, 2024 at his home. He was 65 years old.

Jim was born on June 8th, 1958, in Hyannis to Mary (Wallace) Shields, and James Michael Shields, Sr. He attended Barnstable high school, joined the army, then relocated to Quechee, Vermont, where he grew a successful landscaping business: Shields Lawn & Landscape, and raised his two daughters. He returned to Hyannis where he met his wife, Karalee (Gibbons), and got the chance to welcome four stepson and 10 grandchildren into his family.

Jim was a talented and avid golfer, once winning a tournament, playing the last few holes with one hand. Jim was a "more the merrier" kind of person, making everyone feel welcome. He especially loved spending time with family. He could be found listening to old time radio shows with friends, or being out on the ocean in a boat or clamming. Few people loved being on the ocean as much as Jim.

Jim is survived by his wife, Karalee Shields, two daughters, Lillian Shields and Shaelagh Shields, sons, Andrew, Moran, David Gibbons, and Kristofer Gibbons, three sisters; Kathleen Castellini, Cynthia Darling, and Mary Jo Castellini, and their partners and spouses, as well as 10 beloved grandchildren. He is predeceased by his parents and son, Peter Gibbons.

A graveside service will be held at 10:00 AM on Friday, April 19, 2024, at the Massachusetts National Cemetery.

In lieu of flowers, donations may be made to First Tee Massachusetts.