With his loving family by his side, Leonard Edward O’Leary went home to be with the Lord on Wednesday, December 7, 2022 at Cape Cod Hospital after a brief, but valiantly hard-fought illness.
“Lenny” was born on August 28, 1946 in Worcester, Massachusetts, the youngest child of the late Francis J. and Margaret (Leonard) O’Leary, where his roots to his Irish heritage and Main South neighborhood began and remained a constant throughout his life.
Born, raised and educated in Worcester, Lenny was a graduate of South High School and The College of the Holy Cross, where he was a member of the Navy ROTC program. Commissioned upon his graduation from Holy Cross, he began his service in the Navy and proudly served his country in the naval intelligence division in Pensacola, Florida. Upon returning home to Worcester, Lenny married the love of his life, Kathleen Terrio, and they started their family as he began a long and esteemed thirty-year career with the United States Postal Service – first as a US Postal Inspector and later in varying executive management roles, including time spent at the US Postal Service Headquarters in Washington, DC. He retired in 2001 as Postmaster of Providence, Rhode Island.
Upon his retirement, Lenny and Kathleen (“Kath” as he called her) made a beautiful home for their growing family on Cape Cod where they have resided for over twenty years. It was here that the family shared endless summer days filled with family cookouts, love and laughter and through the fall, Lenny enjoyed family time while passionately rooting for Tom Brady, the New England Patriots and Notre Dame football. - All priceless family memories that will be cherished forever.
Lenny was fiercely devoted to his family, and they always felt blessed to have him as an extraordinarily generous, giving and loving husband, dad and Grampy. Most of all, Lenny was especially devoted to his grandchildren. He was an active participant in each of their lives and marveled at absolutely everything they did. He made them feel so very special and forever loved.
He leaves behind his beloved wife of nearly 53 years, Kathleen (Terrio); his daughter, Meggan E. O’Leary of Charlestown; his sons Michael L. and his wife, Stephanie of Sandy Hook, CT and Kevin P. and his wife, Mary of Sutton; and his cherished grandchildren Addison, John and Grace. He also leaves behind many brothers and sisters-in-law, nieces and nephews, including his beloved nephews Michael, Kevin, Brian and Timothy Boyle, of whom he shared a special bond going back to Maywood Place and whom he was so very proud of. He was predeceased by his siblings Patricia Taylor, Maureen Boyle and Francis O’Leary and we are all comforted in knowing they have all been reunited in heaven with their parents, enjoying their traditional Irish coffee hours once again.
The O’Leary family would like to extend their heartfelt appreciation and gratitude to the entire ICU team at Cape Cod Hospital, especially Ruth Nebrosky, for the extraordinary care and compassion they provided not only to Lenny, but to the entire family.
Family and friends will gather to honor and remember Lenny’s life on Tuesday, December 13th with a funeral Mass at 11:00 a.m. in St. Peter’s Church, 931 Main Street, Worcester. Burial will follow in St. John’s Cemetery, 260 Cambridge Street, Worcester. Calling hours are private. O’CONNOR BROTHERS FUNERAL HOME, 592 Park Avenue is assisting the family with arrangements.
In lieu of flowers, and to honor Lenny’s lifetime love for his Main South neighborhood and St. Peter’s Parish, memorial donations in his memory can be made to St. Peter’s Catholic Church, 929 Main Street, Worcester, MA 01610.