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61 Entries
Jeanne Healy
October 21, 2024
Mr. Hennessey, I think of you often and tonight being one of those nights, I was inspired to google you. I was very sad to find this obituary and although 12 years have now passed since you left this earth, I would still like to send deep condolences to your family and express to you in this writing what a wonderful, caring, calm, compassionate and fair-minded headmaster you were to me at Madison Park in the 1970s, during the most volatile period I ever experienced in this city. My first day of high school coincided with the first day of mandatory busing and the city is in chaos. My bus pulls to the curb and police are lined up as far as I can see as we get off the bus and file through the door. It was so scary and intimidating to this 9th grader, but then the first person I see standing on the other side of the door is you, smiling, reassuring us that we are safe inside the school and then every day thereafter - keeping order and making sure we knew that you always had our back. I often think back on those days and marvel at all you had on your plate and how you handled it all with such wisdom and strength and grace. I will always be grateful for the influence you had in my life and I truly hope to meet you again one day on the other side to thank you personally. Rest well now, kind sir. You deserve all the reward. - Jeanne Healy
Dianne C.
May 8, 2023
I wanted to expressed my deepest condolences, i had remember Mr. Hennessy..during my years in Madison park high..1980's. He really about Care all the students.
Dianne C
Richard Balzarini
January 27, 2016
Mary, Tom was afriend as well as my boss at both Brighton Annex & Madison Park. He was a fine man and a great person. Rick & Carolyn Balzarini
Betty Bridgforth
January 27, 2016
Mr. Hennessey was a good man and a wonderful headmaster to work for. I thank God for his presence in my life. All that knew him were blessed.
Susan Taurinsky
January 27, 2016
I am very sorry for your loss. Mr. Hennessey was the Headmaster at Madison Park High School when I was a student - I can still see him standing in the halls between classes making sure things were uneventful. He was really good to me and I think of him often.
Jim Houhoulis
January 27, 2016
Dear Mary, God Bless Tom's soul and your family. Tom was a great coach and an even greater man.
Lindsey Martinez
January 27, 2016
Sara and Scott - Peter and I send our deepest sympathies for your loss. Peace be with you and your family. Fondly, Lindsey
Karen Parial
January 27, 2016
I'm so sorry for your loss. Your father was such a great man. Thinking of you all with sympathy.
Hackey Kassler
January 27, 2016
My heartfelt sympathy goes out to Tom's family. Tom was a great athelete, teacher and friend. His service as a Selectman for the Town of Brookline was outstanding. All good memories...
Tom Ireton
January 27, 2016
Too many great classmates taken too soon and you, Tom, were one of our best. My deepest condolences to your family.
Thomas Flanigan
January 27, 2016
With Deepest Sympathy and Condolences to all of his family and many friends. May God Bless and Keep HIM always!
Steven Comen
January 27, 2016
As extraordinary as Tommy was in high school, I saw in subsequent years how truly special he was. His humility, empathy, integrity and genuine caring for others were always present. Over the years whenever we chatted, he was most passionate and proud of his family. My most recent memory is the long conversation we had on the boat ride about a year ago with many of our classmates and how quietly fulfilled he seemed. May his memory be a blessing,
JUDITH CHAIT
January 27, 2016
Dear Sara, I am so sorry for the loss of your father. You and your family were so kind to me when I lost my dad as a little girl, and my mom and I have never forgotten how much that support and kindness helped us during such a difficult time. He lives on in your heart and your memories of him: may those memories give you comfort in the days to come. Judith (Dantowitz) Chait
Bud and Betty Small
January 27, 2016
Mary and Family, Our hearts and prayers go out to all of you. Tommy was a great friend for over sixty years. He was a man of great integrity. I know how devoted he was to his family, so proud of his beloved daughters. We will miss him greatly.
Rosa {Jim Lee} Hunt
January 27, 2016
To Mary and children, my sincere condolences. My thoughts and prayers are with you all. May God comfort and keep you always. I will always remember Tom's smile!
David Wagner
January 27, 2016
To all of the Hennessey Family, I'm so sorry for your loss. Tom was a wonderful guy and will be truly missed. My thoughts and prayers are with all of you. David & Michele Wagner
Terry Donahue
January 27, 2016
My sincere condolences to the Hennessey family. Tom was my classmate at Holy Cross. A good man gone to his eternal reward.
Louis Theodos
January 27, 2016
Tommy was a very special person from grammar school on up.Tom was a great athlete but a truly greater friend.God Bless Him
Nancy Fox
January 27, 2016
Sara, Very sorry to hear of your father's passing. You and your family will be in my prayers. Nancy Fox
Melissa & Howard Schwartz
January 27, 2016
We are so very sorry for your loss. Your father was an amazing man and will be greatly missed. Please accept our deepest sympathies during this difficult time. May his memories provide you comfort. xo
Lola Heiler-Stillman
January 27, 2016
Our sincere condolences to Mr. Hennessey's family in this time of mourning. Mr. Hennessey was my daughter's headmaster at Madison Park High School. He was a wonderful positive influence in her life as a student there in the 80's and at ACC. We will never forget his kindness and support to our family as well. Thank you Mr. Hennessey for your love and devotion to Madison's students and their teachers. Leeja Horne Stillman (Madison Park High School Class of 1982)& Lola Heiler-Stillman, her mother.
Bill Balderson
January 27, 2016
Dear Mary: I knew Tom at Holy Cross. He was a man of great character. I share in your loss Sincerely, Bill Balderson
Lynell Crawford
June 15, 2013
R.I.P. Mr. Hennessey the coolest principal in the Boston Public School System...Boston High School Alum will miss you
Deshonna Hamilton
August 23, 2012
R.I.P Mr Hennessy, you will be greatly missed. Your words of wisdom kept me on the right path. Thanks for everything.
Demetria Campbell
August 23, 2012
RIP Mr. Hennessey. You were a wonderful principal & influence on many.
Mari
August 23, 2012
R.I.P Mr.Hennessey
You were a great principal.
Margarita Morton (Cortes)
August 23, 2012
My thoughts and prayers go out to Mr. Thomas Hennessey's family and friends! You were an outstanding principal and a great role model for me during my Boston High School days! But more importantly you were a great friend, I ran into Mr. Hennessey some years ago and he actually remembered me :) we spoke about BHS and then parted ways! Mr. Hennessey you will never be forgotten <3
August 23, 2012
Rest in Peace Mr. Hennessey. Thank you for being such a positive influence in my life. Joanne Kelly, Boston High School-Class of '91
Chanda Dunbar-Smart
August 23, 2012
Mr. Hennessy, you were the best! You truly changed the lives of Everyone that walked through your doors! Thank you for making so many of us feel special and that the sky was and is our limit. May you rest in peace!
Chad Gorham
August 23, 2012
RIP Mr Hennessey may you rest in peace. I am a better man because of you and Boston High School.

Joannie Alvarado
August 11, 2012
R.I.P Mr. Hennessey u were a great principal. Indeed u were very sweet nd caring my condolences to ur family nd close friends, & may God have u in his Glory, Amen.
Maggie Gbeyi
August 10, 2012
RIP Mr. Hennessey.U were a great and caring headmaster to a shy and scared little girl who just came from Africa at Boston High School...May God bless you.
Odeilmaris Rivera
August 10, 2012
Rest in peace Mr. Hennessey. I will surely miss you. you were the sweetest, and warm hearted principal i ever had.
antonia D
August 9, 2012
RIP.. he was my head master at Boston High
Mary Ellen Sheerin
August 8, 2012
I met Tom Hennessey when I went to work at Alternative Education. Tom was a wonderful man who treated all who entered his office with dignity and respect. Tom Hennessey was indeed a "class act". Please accept my deepest sympathy on your loss of this fine man.
Charlotte McCullough
August 3, 2012
I was so sorry to hear of Tom's passing. My thoughts and prayers are with you at this time of sorrow. Tom was my first Headmaster at Madison Park Tech Voc (then known as the Humphrey Center).
Erin Connearney
August 2, 2012
I had the pleasure of working with Mr. Hennessey at Boston Adult Technical Academy. His gentle wisdom and great humor were priceless to colleagues and students. My prayers to his family and friends in their grief.
Rosslyn Riggins-DesRuisseaux
August 1, 2012
My heart felt sympathy and condolences for Mr. Hennessy's family. I worked for him for 15 years at Boston High and think of him often . His personality and genuine concern for his students was clear and he will be missed by many.
August 1, 2012
Please accept my most heartfelt sympathies for your loss…my thoughts are with you and your family during this difficult time. Although no words can really help to ease the loss you bear, just know that you are very close in every thought and prayer.
Greg ( Smooth ) and Valerie Simpson MP
Tehka Bowen
August 1, 2012
Mr. Hennessey was a caring and dedicated person. I was honored to have worked for him during the final years of Boston High School. His legacy will live on through the lives of those that he mentored.
Susan Gomez
July 29, 2012
I am so sad learning of Tom's passing. He was a great guy, funny, and the kids in school loved him (Boston High). It's funny--when I think about him, I imagine him enjoying life and family and friends but that's not the case. Deepest sympathy to his wife and family. Susan Gomez, Boston High.
July 27, 2012
With deepest sympathy,
A fellow hiker in the Eastham Hiking Group,
July 27, 2012
My heart goes out to Mary,family and members of Holy Cross football, track teams and Baghdad Lay Apostalate group that had the honor of sharing lifes journey with Tom.A very specially gifted person in the total sense of the word.Tom thank you for coming into our lives,we love you and wish you peace.Prayers forever Dick Wotruba
John O'Sullivan
July 27, 2012
My sincere condolences to the family and loved ones of Mr. Hennessey. As a youngster from South Boston entering high school in 1976 at Madison Park I was filled with anxiety and doubt. But after meeting Mr. Hennessey as a member of the football team I was immediately put at ease and welcomed by him. We remained friends those fours and his office door was always open to me, for which I am extremely grateful. This world was a better place because of him, and I am a better man for having known him. Thank you Mr. Hennessey - for everything.
Joanne Tisei
July 27, 2012
It was an honor to work with Tom in BPS. He was a kind,bright,funny, and caring educator.He was a mentor, teacher, administrator and role model to many co workers. God Bless.
Ed Reynolds
July 27, 2012
Spent a year in Iraq with Tom at the outset of his journey. He shared his athleticism with us and his Iraqi students, but, more importantly, his optimism, determination, and overall sense of fairness. Thank you, Godspeed, and eternal rest, Tom.
July 26, 2012
So many fond memories of Tom running sprints on Humarock Beach to get into shape for Football. No one could match his speed and endurance summer after summer. He was loved and admired by all. May God Bless and keep his family safe. Our sincere condolances. Bob and Cathy Toran , Walpole, MA
Joe Mason
July 26, 2012
A tribute to an outstanding administrator, math teacher, athlete and coach. But, more importantly,a great person, which in the long run, is worth more than anything!
Barbara Connolly
July 26, 2012
I was fortunate enough to work with Tom during his time with BPS. What a wonderful guy! My prayers go out to the entire Hennessey family.
July 26, 2012
To all Tommy's family, we send our condolences. The Humarock connection is strong -- every time I walk by on the seawall, I can see, in my imagination, the whole family sitting out on the deck. In addition to success with the Patriots, I know his career as an educator touched so many. Maryellen Keenan Mastriani and the Keenan Family
Patty Nock (Pagliocca)
July 26, 2012
Mrs. Hennessey, I am so sorry for you and your family's loss of a great man. Mr. Hennessey, as I called him, being his student, was one of the best teachers I ever had. He was a great role model, mentor, and was great fun. I still remember how bad I felt when I disappointed him by not going into College programs in high school. I wish I could have told him that due to people like him, I did wind up going to college and am considered a very successful business woman today. Thanks, Mr. Hennessey!! (still would feel disrepectful to call him "Tom"...:-)) Rest in Peace.
Michael Matarazza
July 26, 2012
God bless you and your family. Tom was a real frend and graet boss. My prayers and sympathy are with you and family.
Mira Genser Woods
July 26, 2012
Today we remember an incredible man who touched all of our lives in so many ways. A man that always would bring a smile to your face and make you laugh. But also an incredible role model to everyone in the way he lived his life. A fun loving, dutiful, kind and wonderful husband, Father, Papa and friend to so many! You will live on forever in our memories Mr. Hennessey. Much love to all of the Hennessey family at this very difficult time. We are here for you all.
July 25, 2012
We loved our summers on Hummarock Beach near your family, the Mahoneys & the Flanagans. It was a great time growing up. Riki Blanchard
Drew Wintemberg
July 25, 2012
The thoughts and prayers of the Time/Warner Retail family are with you all. Know we are thinking of you.
July 25, 2012
My prayers and sympathy are with the Hennessey family during this difficult time.May you rest in peace Tommy.
Jim Flynn
Sarasota,FL
John MacDonald
July 25, 2012
Tom has been an important influence in my life. He was such a great person for whom I have a tremendous amount of respect.I am very thankful that I knew him, worked for him and most of all had him for a friend
Charles Hayes
July 25, 2012
Mary , God bless you and your family. Tom was my friend and a fine headmaster at Boston High. Charles and Margo Hayes
Lisa Robb
July 24, 2012
How we loved Uncle Tom and we will miss him very much and cherish all our memories from Scituate, Humarock, Bonad Rd and Orleans and on and on. Everytime you eat a stuffed clam or play with a child remember our dear Uncle Tom. All our love we send to Mary and the girls. The Robb Malones
Pete Frasca
July 24, 2012
Mary-
Tom- a good guy-taken to soon
cherish your memories-
Andrew and Drew Hennessey
July 24, 2012
RIP Uncle Tom--heart goes out to Mary, Sara, Tina and Maria.
Great Guy
Showing 1 - 61 of 61 results
Funeral services provided by:
Bell-O'Dea Funeral Home - Brookline376 Washington St, Brookline, MA 02445

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