(Jimmy) of West Roxbury and formerly of Natick died on July 19, 2020 after a period of declining health. Jimmy was born to Myril and Helen (Shea) O'Leary on October 20, 1936 in Needham, MA. He was raised in South Natick and attended Natick public schools. After school, he proudly joined the Navy and served from 1955 through 1959 after which he was honorably discharged. During his military career he spent some time stationed at Point Mugu, California.
He was brother to six siblings, including Sister Clarine O'Leary of Sydney Mines, Nova Scotia and the late Myril R. O'Leary, Jr., Jean G. Cohan, Nancy L. Topham, Alice E. O'Leary and Arthur C. O'Leary.
Jimmy had four children: James O'Leary, John O'Leary, both of Natick, Jean Flem of Framingham, and Joy Murphy of Shrewsbury.
A self-employed truck driver and mechanic for most of his post military career, he enjoyed long drives delivering cargo wherever needed. He lived on the North Shore for many years including Reading and Burlington. Hunting and fishing were two of his favorite hobbies. An avid sports fan, he enjoyed watching New England sports teams and NASCAR races.
Jimmy's niece Brenna would like to thank the compassionate staff at the Brockton VA Hospice Care unit for their devoted care of Jimmy during his final weeks.
Funeral service at John Everett & Sons Funeral Home 4 Park Street NATICK COMMON Sunday July 26 at 10am. Relatives and friends are kindly invited to attend. Visiting hours Sunday, July 26 from 9-10am in the funeral home. Interment Glenwood Cemetery, Natick. Due to the Coronavirus, guests are required to wear masks and practice social distancing in the funeral home.
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