Leo Francis O’Leary, 93 of Weymouth, originally of Milton, passed away peacefully on Saturday, March 16, 2024 surrounded by family. Leo was the beloved husband of the late Barbara Kuja O’Leary . They were married 65 years, and she was the love of his life and best friend until her passing in late 2022. They lived and raised their family in South Weymouth and moved to Dennis in retirement.

Leo proudly grew up in Milton with his 2 brothers and 2 sisters. He was the 4th of 5 children. He is survived by his brother, Father Jim O’Leary of Yarmouth. He graduated from Milton High school and remained lifelong friends with many of his classmates.

Leo was the loving father of 4 children. Michael and wife Mary Lou of Norwell MA, Jill and her husband Brian of Stowe, VT, Chris and his wife Susan of Ipswich MA, and Julie and her husband Bill Delaney of Duxbury, MA. He enjoyed spending time with each of his 11 grandchildren - Patrick O’Leary (wife Micaela), Jon O’Leary (wife Vanessa), Kellie O’Leary, Seamus, Catherine, Tyler and Christopher Mullin, Cameron and Madison O’Leary, and Sean and Keira Delaney. He was great grandfather to Benson and Belle O’Leary.

Leo and Barbara enjoyed skiing at Sugarloaf, Maine with family and friends for more than 3 decades. In retirement they enjoyed living a relaxed life on Cape Cod. Leo and Barbara relished the performances of the Cape Cod playhouse, spending time at Cold Storage Beach, and were active members of the parish at Our Lady of the Cape.

Leo was a soft ball enthusiast, starting at Cunningham Park in Milton and continuing into retirement in the Cape Cod over 70 men’s league well into his 80s. He was also very active in coaching his kids from farm league through senior Babe Ruth baseball as well as girls’ softball.

He worked for Chase Parker, an industrial distributor, straight out of school and went on to found L.F. O’Leary Company, a precision measurement distribution company. The company is still thriving today with his oldest son Michael with third generation, Jon O’Leary.

A Mass of Christian Burial will be celebratred Saturday, March 23, 2024 in St Agatha's Church at 10:30 am. Visiting Hours in the Dolan Funeral Home, Saturday from 9 - 10 am. Interment Milton Cemetery.

In lieu of flowers contributions may be sent to either, Alzheimer's Association, 309 Waverly Oaks Rd., Waltham, MA 02452 or to Weymouth Food Pantry, P.O. Box 890009, Weymouth, MA 02189.