Ann Monica (Holohan) O'Leary

Ann Monica (Holohan) O’Leary, a lifelong resident of Worcester, Massachusetts, passed away peacefully Sunday, June 8, surrounded by her family. She was 86 years old.

Ann married the love of her life, John T. O’Leary, Jr., and together they built a beautiful life filled with faith, family, and hard work. They raised three children who were the pride of their lives: Patricia A. O’Leary Engdahl of Worcester, Christine A. Devine and her husband Gregory of Barre, and John A. O’Leary and his wife Megan (O’Sullivan) of Boston.

A devoted great-grandmother, Ann’s heart was fullest when she was with her grandchildren: Ellie and her husband Michael, MaryPat and her husband Patrick, Katie and her husband Conor, Billy, TJ, and Gracie. She lit up even more brightly with the arrival of her great-grandchildren, Rosie and Jack, who brought her immense joy and pride.

Born on September 8, 1938, Ann was the daughter of George A. and Dorothy M. (Grady) Holohan. She grew up just outside Newton Square, in a home filled with warmth, stories, and the sounds of her father’s nearby family business—Holohan Brothers Cafe on Park Avenue, a local institution.

Ann attended Blessed Sacrament Elementary School and St. Peter’s High School before earning her B.A. and M.A. in elementary education from Worcester State Teachers College. From there, she began a life dedicated to teaching, learning, and building community. She taught in several area schools, but found her true vocation as an ESL (English as a Second Language) teacher. She worked for many years with Worcester Adult Education and later volunteered at the Worcester Senior Center after her retirement. She cherished her students deeply, often marveling at the cultural richness they brought into her life. She took great joy in the stories, recipes, and tokens of their homelands they shared with her, and she considered herself lucky to learn as much from them as they did from her.

In earlier years, Ann and Jack co-owned Courtside, a local sneaker store, a venture that combined her love of community and family collaboration.

Ann lived her faith with quiet constancy as a devoted member of Christ the King Church. In the 1980s, she and Jack were deeply involved in the parish’s youth ministry, serving as CYC advisors and giving generously of their time—chaperoning dances, organizing field trips, and always showing up with a chocolate cake. She also treasured her friendships, especially her years with the “Friday Afternoon Club”, and the Worcester State Alumni. 

Ann will be remembered by her family for her warmth, her flair, and her steadfast love. She had a gift for making every holiday feel special—Valentine’s Day, St. Patrick’s Day, the Fourth of July—always complete with themed decorations, festive outfits, and thoughtful gifts for each grandchild. Her impeccable style—her brooches, her coordinated shoes and handbags—were a reflection of the care she brought to all areas of her life.

Ann’s funeral Mass will be held Tuesday, June 10, at Christ the King Church, 1052 Pleasant St., Worcester. Calling hours will be from 9:00 to 10:45 a.m. in the church, followed by a funeral Mass at 11:00 a.m. She will be laid to rest beside her beloved husband Jack in St. John’s Cemetery.

In lieu of flowers, donations may be made to the Worcester State Foundation, Inc.