SOUTH PORTLAND- Timothy James O'Leary, 83, of South Portland, Maine, died in his home at Sable Lodge on January 30th, 2026, after a long, courageous battle with cancer.
Tim was born in Portland in 1942 to James E. and Marion R. (Horan) O'Leary. He graduated from Cheverus High School, St. Francis College, and went on to receive his master's degree in history from Niagara University.
Tim met his sweetheart, Joyce Ann Day when he was in his early 20s. He often said he was a better person when he was with her. They enjoyed a long courtship while he finished college, and Joyce completed nursing school. Tim, ever the comedian once told his grandson that: "Your grandmother followed me home one day, so I kept her, and we eventually got married (in 1966)".
Following his graduation, they moved to Clinton, Iowa, where he became a professor at Mount Saint Clare College, teaching history and Dogmatic Theology. He also created and taught a course in Black History.
While in Iowa, Tim and Joyce began their family, raising two beautiful daughters of whom he was immeasurably proud. When the family returned to Maine, he spent countless hours as their biggest cheerleader at all their track meets, basketball and softball games.
In Maine, Tim worked for Carr Brothers, State Paper and later retried from Federal Distributors.
Never a fan of long, cold New England winters, Tim and his wife moved to Tucson, Arizona in 2001, where he became a realtor for Long Realty. They made Tucson their home for over 20 years, returning to Maine in 2023 to be with family.
Tim possessed a strong social conscience and volunteered tirelessly. He served as the Director of Cumberland County Child Abuse and Neglect Council. He was part of the committees that procured lighting for the Deering High and Portland High Athletic fields. While in Arizona, he was on the Board of Directors for Top Dog, and he served as vice president, and then president of his church council.
Tim was a voracious reader throughout his lifetime. Other passions included a wide variety of music (particularly Buddy Holly, traditional Irish music and opera), drawing, Japanese culture and gardening.
He was known for his quick wit and droll, playful sense of humor. His reputation as a sharp, debonair dresser was legendary. He prided himself on always being "put together", because as Irish poet Oscar Wilde said: "The only way to atone for being occasionally overdressed is by being always absolutely overeducated".
Tim was preceded in death by his parents, James and Marion. He is survived by his wife and two daughters: Jennifer and her husband Jay Jones, Katharine and her husband Tony Decker; 2 grandchildren; Ryan and Haley Ball, sister Judith and her husband Robert Balko, brother Robert O'Leary, and several beloved nieces and nephews.
A celebration of life will be announced at a later date. In lieu of flowers, donations may be made to Hospice of Southern Maine, 390 US Rt. 1 Scarborough, Maine 04074, www.hospiceofsouthernmaine.org . The family would like to thank the entire team for providing extraordinary, compassionate and dignified care to Tim.
Arrangements have been entrusted to Poitras Funeral Homes, www.mainefuneral.com