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Katherine B. (O'Keefe) O'Leary

September 13, 1942 ~ October 27, 2020 (age 78)

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SALEM – Mrs. Katherine B. (O’Keefe) O’Leary 78, of Salem, beloved wife of the late Richard A. O’Leary, died Tuesday, October 27, 2020, following a lengthy illness. 

Born in Salem, she was the daughter of the late Richard and Helene (Reddy) O’Keefe. She was raised and educated in Salem and was a graduate of the former St. James Girls School and the former St. James Girls High School. She continued her education at Bentley College. She was an educational pioneer as she earned the recognition as the first female Graduate of Bentley College in 1964. 

Mrs. O’Leary was certainly well educated, but overall, she was incredibly intelligent, honest and bright, especially with numbers. She was elected the Essex County Treasurer for three terms. She was also the Cofounder of O’Leary Financial Services with her daughter Bethann. She was a member of the Essex County Retirement board as well as the City of Salem Retirement Board. In addition, she was a member of the Salem Parks and Recreational Department and served one term as President of the Massachusetts Retirement Board. 

Athletics were a family tradition and sports played a large part of Katherine’s life. She was an exceptional athlete and would often be found playing with the boys. She shared her love of sports with others through coaching. She was a revered Softball and Field Hockey coach throughout New England. She was the Salem High School Varsity Softball Coach and the Salem State College Varsity Softball and Varsity Field Hockey Coach for many years. She was truly a legend at Salem State and paved the way for other women looking to advance in the sports field. She was a great mentor, teacher and motivator of young people. She was also the first woman Softball Umpire in New England. 

Katherine and her beloved husband Richie were a love story made in heaven. They were attached at the hip and devoted to one another and their family. They travelled all over the world and enjoyed going on cruises and spending time in Las Vegas. She could often be found cheering on her children and grandchildren at their sporting events and never missed a game. Her love of sports earned her the title of Red Sox and Patriots “expert” by family and friends and she passed her passion for sports on to her family. She will be deeply missed. 

Katherine is survived by her daughters, Maureen Ouellette and her husband, Steven of Salem and Bethann Jellison and her husband, Robert of Salem, her son, Richard O’Leary Jr. and his wife, Nicole of Salem, her grandchildren, Hayley, Tayla, Jessica, Kyle, Kory, Bobby, Cassadi and Ryan, her siblings, Mary Lou Tuttle of Salem, Michael O’Keefe of Venice, Fl, Joanne Riccciardiello of Naples, Fl, sister-in-law Barbara Sirois of Salem, MA and several nieces and nephews and extended family. She was also predeceased by her sister Judy Kidney. The family would also like to thank Jean, Betty-Anne, and Angel for their wonderful care of their mother during the last weeks of her life.

 ARRANGEMENTS: Her funeral Mass will be held in St. James Church, Federal St., Salem, Monday, Nov. 2nd at 10 A.M. All attendees must register to attend her funeral mass by clicking the RSVP link below. Visiting hours at O’Donnell – Cremations – Funerals – Celebrations, 84 Washington Sq., (at Salem Common) Salem, Sunday, Nov. 1st from 3 to 6 P.M. All attendees are required to wear face coverings, practice social distancing and are respectfully asked for no physical contact with the family. There will be a public celebration of both Richie and Katherine’s life to be held in the spring of 2021. Expressions of sympathy may be made in Katherine’s memory to Care Dimension, 75 Sylvan St., Danvers, MA 01923. To share a memory, offer a condolence or register attendance at church, please visit

To send flowers to the family or plant a tree in memory of Katherine B. (O'Keefe) O'Leary, please visit our floral store.


November 1, 2020

3:00 PM to 6:00 PM
The O'Donnell Funeral Home
84 Washington Square
Salem, MA 01970

Funeral Mass
November 2, 2020

10:00 AM
St. James Church
160 Federal Street
Salem, MA 01970

Please note

Attendance is limited to a maximum of 71 people. Family and friends planning to attend are kindly requested to RSVP to reserve their place

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