Cover photo for Thomas Patrick Callahan, Jr.'s Obituary
Thomas Patrick Callahan, Jr. Profile Photo

Thomas Patrick Callahan, Jr.

September 27, 1951 — November 25, 2023


Thomas Patrick Callahan, Jr.

Thomas Patrick Callahan, Jr.  went by many names throughout his life…. Tom, Tommy, Step, Inspector, TC and his proudest name of all - Papa Cal.  To all who knew him, he was a loyal husband, devoted father/grandfather, brother and friend that would do anything, at any time, for the people he cared about.  He lived by a solid code of right and wrong, and instilled it in his family.  He was a man of simple pleasures - a two hour workout, Coors Lights, Chinese food, a sleeve of chips ahoy cookies and watching a movie or documentary with his bride of 38 years was the perfect Saturday night.  

By Tom’s side for 38 years was his beloved wife Carol.  Carol not only held the title of his Best Friend, but was recently promoted to “life saver”.  Before internet dating websites were a thing, you had to rely on your parents to hire an attractive young Northeastern University graduate to paint your house in the summer. After coming down off a ladder with his painter's hat on, Tom asked Carol on a date…and the rest is history.  He introduced her to running (and marathons/road races), racquetball (and tournaments) and endless fitness clubs to fill up every hour of the day that they were not at work. Trophy after trophy, days of screaming over how he lost a match or pulled a muscle, and the anticipation of the next pay per view boxing match was just a way of life.

Together they embarked on a life together raising two sons, Bobby and Paul,  in Quincy, Massachusetts.  Tom raised them as his own and always instilled in them drive, competitiveness and a good sense of humor.  Through thick and thin, good times and bad , they stood together as an inseparable team committed to being there for each other, their friends and their family.  Racquetball tournaments became weekend getaways, friends from the gym became extended family and racquetball courts became their home away from home.      

Tom was a fierce competitor, a true athlete that woke up every morning with his mind focused on how great his workout was going to be that day.  Running, boxing, tennis, racquetball, riding his bike, pickleball, Tom pushed himself to be the best.  It was in this quest that he found his greatest and longest lasting relationships with men and women that he called friends.  To this day friends like Kevin and Paul Corrigan, Hal Gabriel, Jim Bove and endless others were always on his mind as some of the best athletes he had ever known.  Every match was a reunion, every tournament was a holiday and every interaction with his opponents was a friendship in the making.  Tom might not have liked you personally, but he always respected those people that made the effort to train, compete and leave it all out there. 

For over 60 years, Tom traveled throughout the US honing his craft and elevating his game.  From running in an apropos 11 Boston Marathons (the number matching his intensity level), hundreds of racquetball tournaments and thousands of hours in the gym, he built the Tom Callahan Brand.   This brand also carried over into Tom’s professional career.  As an individual contributor and manager of Special Investigative Units at numerous insurance companies, Tom always put forth his best effort with the maximum amount of integrity.  As always, he gravitated to professionals that he considered to be the best.  Investigators, attorneys, police officials, Tom extended his support and friendship to all of those who held the same values of his brand.     

Whether in the gym, on a court or out on investigations, Tom traveled with the pride of his family name.  Tom was the spitting image of his father and namesake, Tom Sr..  He would end every conversation about his sister Karen with “she is the smartest woman I have ever met”.  The pride of his brother Chris serving our country.   His admiration for his youngest brother John for not only having an insatiable competitive nature but for also having  “the greatest sense of humor” he had ever seen. These were the things that Tom wore on his sleeve with pride every day of his life.    

As his sons grew older, so did their family.  Bobby married his college sweetheart,  Jennifer, and Paul married his high school sweetheart, Lyndsay.  Tom embraced them as his daughters and extended his protective nature over them the only way Tom knew how.   Learning about their careers, travels, and never ending home projects offered a limitless opportunity for his other favorite pastime - asking questions.  He was always proud of the four of them and enjoyed their adventures of going out to dinner, attending events or just grabbing a beer. Little did Tom know that the best was yet to come.

In 2012 the world according to Tom Callahan changed FOREVER.   Unbeknownst to those close to him, Tom had a soft side.  A gentle side.  A side that people had never seen.  Three children came into his life and made him a Grandfather.  The origin of Papa Cal.  Jack, Matthew and Sloane, came into his life and things changed dramatically.  18 months later, Quinn arrived and she turned Papa Cal into the softest human on earth.  2 years after that Sawyer arrived and the 5 grandchildren would now begin to help Papa Cal and Mimi (Carol) start to write their greatest chapter.  For those of you who knew Tom for his fierceness and competitiveness, you would be shocked to know him with his granddaughters and being the ultimate softie for his girls.  From hours of tennis at Clear Pond, to riding bikes, to dance recitals, to soccer and baseball games, Papa Cal was a new man living through his grandchildren competing and leaving it all out there.    

With the love of his family, the joy of his grandchildren, and his new found love of pickleball with friends in Walpole, Norwood, Mills, Newton, East Boston and only God knows where else, Tom was writing the greatest chapter of his novel.  He was happy. He was thankful. He was grateful.  And he will always be loved and admired by those fortunate enough to have known him.

Rest in peace Papa Cal

Beloved Husband of Carol Jean (Wolinsky) Callahan.
Loving Father of Robert D. Picciano, and his wife Jennifer J.N., of Medfield and Paul M. Picciano, and his wife Lyndsay, of South Boston.
Cherished Papa Cal of Jack, Matthew, Sloane, Quinn, and Sawyer.
Brother of Karen M. Callahan of Marlborough, Major General Christopher P. Callahan, and his wife Donna, of North Kingstown, RI, and John J. Callahan, and his late wife Amy, of Milford.
Also survived by several nieces and nephews.

Relatives and friends are kindly invited to attend Thomas's Visitation on Sunday, December 3rd, 2023 from 2:00 - 5:00 pm in the James H. Delaney & Son Funeral Home, 48 Common Street, Walpole.

A Funeral Home Service will be held Monday, December 4th, 2023 at 11:00 AM. Interment will follow at the Saint Francis Cemetery in Walpole.

In lieu of flowers, memorial donations in Thomas's name may be made to the Boston Children's Hospital; 401 Park Drive, Suite 602, Boston, MA 02215 or by visiting

To order memorial trees or send flowers to the family in memory of Thomas Patrick Callahan, Jr., please visit our flower store.

Past Services


Sunday, December 3, 2023

2:00 - 5:00 pm (Eastern time)

James H. Delaney & Son Funeral Home

48 Common St, Walpole, MA 02081

Enter your phone number above to have directions sent via text. Standard text messaging rates apply.

Funeral Home Service

Monday, December 4, 2023

Starts at 11:00 am (Eastern time)

James H. Delaney & Son Funeral Home

48 Common St, Walpole, MA 02081

Enter your phone number above to have directions sent via text. Standard text messaging rates apply.


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