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Leo Stapleton Obituary
View the online memorial for Leo D. Stapleton
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Memories and Condolences
for Leo Stapleton
Sponsored by O'Brien Funeral Home - South Boston.
Mike McAllister
May 26, 2025
Chief Stapleton, you exemplified what being a fireman truly is. In this business there are some who stand out amongst those who stand out. You are that person.
Rest easy Chief from all of us, your brothers.
Bill Connors
April 23, 2025
I walk every day down at the pumpy that´s the pumping Station in houghs neck.and every day I say thanks Commish for keeping us safe in all those busy years you always be remembered by us"jakes" always (peace be with you Leo)
BFD duffer Bii Connors
April 30, 2024
You will always be missed and in our hearts Commish thanks for all those years you keep us safe sea ya one of these days keep the ball in the shot grass up there
Michael Heraty
July 9, 2023
I met Leo when he came to my house and he signed my copy of "Commish" in 1991. I played the sax at a concert at the Hatch Shell on the Esplanade a month later. He came to my gig. I saw him at the Boston Firefighters Ball a couple of times. I attended one of his lectures and he wrote a letter of recommendation for me in 2000. He was a kind-hearted humble man and a great friend.
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Beano
April 24, 2023
There was a time, in time, when complete men walked the Earth. The Deputy was one.
denise c mcleod
April 23, 2023
I always felt good when I ran into Leo and Doris. He always said something kind to me. Our Mom was his cousin, I used to visit Nanny and Unkie which Leo had the same smooth talk like his father. They don't make men like him any more, kind hearted what a wonderful man he was
God rest his soul
Denise(O'Donnell) McLeod
Bill connors
April 23, 2022
Love talking with the Commis a real jake and the camaraderie out on the golf course will never be forgotten miss you Leo.
Jim Shake Jr
May 12, 2021
I'm sorry to read of the passing of "The Commish". Having read some of his early writings, it was indeed an honor and a pleasure to have met him many years ago at the New England Association of Fire Chiefs Convention. "Commish" had just come out and he was kind enough to sign my copy. "The Commish" will certainly be remembered for many things - leadership, tactics, innovations - most of all he will be remembered as a firefighter to the core, a jake's jake. My condolences go out to the Stapleton Family. Rest in peace Chief, God Bless.
Jim Shake Jr
Past Chief
Niantic Fire Department
Niantic CT
Robert Breen
May 3, 2021
Thank you for all the innovations, progress, made under your leadership. The great understanding for those that served under your command and direction on the fire ground. I will never forget you or what you have done. Beano
Agnes Stapleton Rath
May 1, 2021
Sad to learn of your death; a great son and father. Only three of us in our generation of Stapleton/Baldwin are now left: Frank Stapleton of Dedham, MA and Agnes Stapleton Rath of Madison CT. Peace to us all, the Stapletons.
Jack and Joan Joyce
May 1, 2021
Sorry for the loss of a wonderful person and a great boss. He will be in our hearts and minds forever.
Jack and Joan Joyce
Priscilla O'Donnell/Hatch
April 30, 2021
To all my Stapleton cousins,
Leo always brought a smile to my face whenever I saw him. He always had a funny story to tell. I am sure he inherited his story telling talent from Nanny. He and Doris were a wonderful couple. They loved each other very much and were so proud of each of their children. He was a South Boston treasure and I am honored to have been a member of his extended family.
Fred Postel
April 30, 2021
Sincere condolences to the Stapleton Family! Leo was a good friend, a professional, fun to be with, knowledgeable about the fire service and willing to share his knowledge with all, and he did! We became good friends soon after meeting in 1989 and had many fun times together with our wives and other Boston Jakes especially Marty and Ellen Pierce. Leo was a great firefighter, leader and chief! It was always good to see Leo after his retirement. I feel very grateful to have known him, to have been his friend and to have learned about Boston and the Boston fire Department from him.
Fred Postel, Retired, Chief of Department, San Francisco Fire Department
PS: In SFFD Jakes are called Jakeys
Dave McEttrick
April 30, 2021
A great American! I remember as a kid while living in Chicago, Leo had called the house to talk to my dad and my younger brother answered the phone. Mike was probably 6 at the time. After hearing Leo's voice, Mike asked Leo if he was Santa Claus! A great memory that we fondly recall routinely. Always enjoyed the visits and conversations with Leo! Best wishes to the family as you celebrate his life!
Edward O’Toole
April 30, 2021
Dear Family,
Leo was an amazing person, firefighter and Boss. We had amazing careers together and loved every minute. RIP
Stapey, Commish.
Edward O’Toole BFD, Aide to Commissioner Stapleton (ret)
Michael Heraty
April 29, 2021
My condolences to the Stapleton family. I met him in 1991 when I read his books. He visited me at my house in the summer. He signed a copy of his book. He went to one of my gigs when I played the sax. I saw him a couple of times at the Fire fighters Ball and I attended one of his lectures called "Leadership in the Firefighting Profession." We talked after the lecture. He sent me a card when I graduated with a Fire Science degree and he wrote a letter of recommendation for me. He was a great friend. I'll miss him always.
Anne Rheault
April 29, 2021
My condolences in the passing Commissioner Stapleton's Family and Friends ,along with his follow firefighters.
Such a wonderful person .
My He Rest In Peace . Again my condolences on your loss .
Tim Campbell
April 29, 2021
My heart hurts to hear the news. I’ll always remember the stories that the Commish would tell in the booth at any number of fire shows over the years. Rest in Pace, Leo. I’ll miss your genuine smile and good nature very much.
Jack McKenna & Family
April 29, 2021
Our deepest sympathies to the entire Stapleton Family. Words can't express our love of Leo and our sadness in his passing. R.I.P. , pal
Gerry
April 29, 2021
Dear Family , Sorry for your loss, my thoughts and prayers are with you all. What a full and accomplished life your Dad has lived surrounded by loving children.
Nick Dimarino
April 29, 2021
I am sorry for your loss. I had the pleasure of working with Leo Stapleton when he was the Fire Commissioner. I was in the Other Division when he was a Deputy. As a firefighter he was always concerned about our safety and getting us the best equipment available to make our job safer. I was also in the Golf League at Easton Country Club for a short time and enjoyed see him each week. Thank you for being there for us Commish RIP
Denise O'Donnell-McLeod
April 29, 2021
To Leos family, I enjoyed hearing stories from Nanny about raising her boys!
I used to love running in to Leo and Doris, usually at St. Brigids, Doris sang beautifully, and Leo always said something kind to me, he was always a gentile soul, may he rest in peace
God Bless
Denise
Mark hoban
April 29, 2021
A good friend of my dad roger hoban of south Boston,
And a member of the wildcats.rest in peace mr.Stapleton.
A.Chase
April 29, 2021
We were sad to hear of the loss of our dear friend. Leo was a wonderful human being, a great role model for the BFD and mentor to many a young jake in Boston and beyond. Our prayers are with his family that they continue to make him proud. Chubby Chase, Retired BFD, his wife Andrea and family
john howard
April 29, 2021
The best boss the city of Boston ever had and a true friend to all,
Patricia Ritz
April 28, 2021
Pops was one of the best men I ever knew. I loved him like a father.
My deepest sympathies to all those who loved him. He will always hold a special place in my heart
Willie K Harris (BFD ret)
April 28, 2021
Rest In Peace Commissioner. One of the BFD’s best and a true gentleman.
Pat and Tom marsters
April 28, 2021
Rest In Peace Leo. Was a pleasure knowing you and reading your books. You were the best of the best. My husband says you were a great Commissioner- he was proud to have known you. Until we meet again. Rest In Peace. Tom Marsters retired BFD. Pat Marsters.
Bill Connors
April 28, 2021
The commish was the best of the best kept all us jakes pretty safe especially during the seventies and eighties . Great guy to play golf with ,peace be with you Leo thanks for the memories
Barry Stafford
April 28, 2021
The Commish appointed me in '84. I know he went out on a limb to do it. He made my dream come true & allowed me to achieve the success I have. I will forever be grateful for the faith & confidence you showed in me. Boss, I hope I made you Glad you made this choice. Thank you so very much! Rest in peace.
Judy Gibbs
April 28, 2021
Best Uncle ever! My beloved Uncle Leo, I will miss our conversations and all the love you showed and your words of wisdom. You were a remarkable human and will be missed. RIP, and hello to Aunt Doris for me. Sleepless in Seattle, Judy Gibbs (Parsons) OXO
Bill Noonan
April 28, 2021
Leo was a great friend and boss..he will be missed....I have great memories...RIP old friend....
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