Paul K. O'Leary

  • Born: December 30, 1935
  • Died: September 10, 2020
  • Location: Stoughton, Massachusetts

Farley Funeral Home

358 Park Street
Stoughton, MA 02072

Tel. (781) 344-2676

Tribute & Message From The Family

Message From The Family

Thank you for your support during this difficult time. Please enhance this tribute to Paul by adding your memories and photos.

Paul K. O'Leary of Stoughton and East Sandwich passed away peacefully on Thursday, September 10th, 2020 at the Copley at Stoughton.

He was predeceased by his wife Diane Deltano O'Leary in March 2019. He leaves his two children, Erin Kittell and her husband Stephen of Beverly, and Justin O'Leary and his wife Kathleen of Worcester. He was the beloved Pops of three grandchildren: Ethan Kittell and Patrick and Kate O'Leary. He is also survived by many nieces and nephews.

Paul was born in South Boston, the son of the late Jeremiah and Muriel O'Leary. He was predeceased by his brother Gerald O'Leary. Paul received his undergraduate degree from Boston College. He did post graduate work earning a master's degree in education from Boston State College.

He was an educator for over 40 years starting in the Stoughton school system as a guidance counselor and then moved on to become an administrator in Southeastern Regional Vocational Technical High School where he was a superintendent for 13 years.

Paul and his wife Diane loved to travel throughout the United States and abroad. He cherished spending time with his family on the beach in Sandwich.
The family would like to thank all the nurses and staff at the Copley for their loving care and support that was given to Paul during his stay.

Family and friends will honor and remember Paul's life by gathering for calling hours at Farley Funeral Home ~ 358 Park Street, Stoughton on September 19th from 8:00 – 8:30am followed by a Funeral Mass at St. James Church 560 Page Street Stoughton at 9:00am. Burial will follow in Holy Sepulchre Cemetery, Stoughton. Masks and social distancing are required.

In lieu of flowers, donations in his memory may be made to Boston College, Office of University Advancement Development, 140 Commonwealth Avenue, Chestnut Hill, MA 02467.


Condolence & Memory Journal

Please accept my condolences . I'm so sorry for the loss of your loved one. May the word of God comfort and strengthen you. 2 Thessalonians 2:16,17

Posted by D T    September 22, 2020


My first years at Southeastern had Mr. O'Leary at the helm, at which time I collected many fond memories. My sincere sympathy to his family. on his passing. God Bless you Mr. O'Leary!

Posted by Ginnie Giovanello - Brockton, MA - Teacher   September 14, 2020

Dear Erin and Justin and family,
Our sincerest sympathy to you as you say goodbye to your Dad.
He is probably having a beer or volleyball game on some heavenly beach volleyball court with Linc who died a few weeks ago on July 29th. We had a lot of fun with our families in the summer, visiting from Mattapoisett to Sandwich beaches.
Paul was my first boss as Pupil Personnel Director at Southeastern, when Ch 766 and IDEA were in their infancy. We had a very cohesive dept in those years and as long as we did our best for our students, Paul encouraged our Ideas and methods so that each student in SPED Could be successful.
I'm sure your Mom is saying Oh, you know Paul, he wants to to travel so off we go! Our thoughts and prayers are with all of you.
Judy,Stephanie and Bessy Medeiros and family

Posted by Judy Medeiros - Mattapoisett & Naples, FL - Friend   September 13, 2020

Our deepest condolences.

Posted by Charlie Ahern - Melbourne Beach, FL - Friend   September 13, 2020


We are deeply saddened to hear of Paul's passing. We offer our sincerest condolences to Paul's family during this difficult time. We fondly remember the impact he had on our school. Sincerely, The teachers of the Southeastern Regional Vocational Technical High School Federation.

Posted by SERSD Teachers' Federation - Easton, MA - Coworker   September 13, 2020

Mr. O'leary was my Social Studies teacher. Sorry to hear of his passing

Posted by Diane Catalano Alden Manory - Charlestown, NH - Student   September 12, 2020

It is with great sadness that I write this note to Erin, Justin and their families on the passing of their father and grandfather. I had the privilege to work with Paul at UMASS Boston for almost ten years. He was an outstanding educator, very smart and dedicated to his profession. Paul loved his South Boston heritage but never stopped talking about his wife Diane, children and grandchildren. He was very proud of his family with all their accomplishments. Paul was a very good man, a great friend and will be missed by all who knew him May he rest in peace.

Posted by Richard McLaughlin - West Roxbury, MA - friend   September 12, 2020

Outstanding educator and administrator,Paul dedicated his career to the needs of all his students. A wonderful loyal friend and colleague whose advice and wisdom made him a great mentor.He was proud of his South Boston Irish heritage and was respected and admired by his multitude of friends. May you Rest In Peace my dear friend

Posted by Jimmy Murphy SHS Massasoit CC - Coworker   September 12, 2020

Paul; our six years together at SER was an adventure to be sure. Godspeed Paul, RIP. John Avery

Posted by John Avery - Ormond Beach, FL   September 11, 2020

Dear Justin and Kathy and children: we are sending condolences on Justin's dad's recent passing. May he be in peace and joining his wife forever. Our love to all. Diana and Paul Browning

Posted by Diana/Paul Browning - Vero Beach, FL - Family Friend   September 11, 2020

Family Album