William Thomas "Tom" Generous, Jr.
February 20, 1939 - October 25, 2022
Carrboro, North Carolina - William Thomas "Tom" Generous, Jr. died on October 25, 2022 in Carrboro NC. Born in Pawtucket RI on February 20, 1939, Tom was educated at St. Raphael's Academy 1955, Brown University 1963 and received a PhD in American History from Stanford University in 1971.
Tom spent 8 years proudly serving in the United States Navy, lastly as a lieutenant on the U.S.S. Vance. He authored seven books, including Swords & Scales, The School Upon the Hillside and Sweet Pea at War.
Tom married his beloved wife, Diane, in 1964 and in 1971 they moved to Wallingford CT, where he made his career at Choate Rosemary Hall, teaching, coaching and serving as housemaster for 28 years. They retired to Carrboro, NC in 1999.
Tom was predeceased by his wife Diane. He is survived by his two daughters, Michelle Generous and Suzanne Prentice (Michael), grandchildren MaryJane and Tommy Prentice; his special lady, Patti Gamin; sister Donna Dufault, nieces Jodi Hayes (Scott) and Rebecca Roberts (Jamie Fisher); sister-in-law Nancy McMillan, niece Lauren Morawski; uncle Jack Myette; and several cousins, including Pamela Zappardino (Charles Collyer), Michael Myette (Patti), Barbara Krakowsky (Arnie).
As per Tom's wishes, burial will be private. Celebratory services will take place in Carrboro, NC (February) and Wallingford, CT (April.) Check back in January 2023 for details. For online condolences Visit www.wallingfordfh.com Arrangements are under the direction of the Wallingford Funeral Home.

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Published by & on Nov. 13, 2022.

Memories and Condolences
for William Generous

Sponsored by Wallingford Funeral Home.

30 Entries

Raymond Church

July 14, 2023

I was very fortunate to serve with Mr. Generous in the Navy. Although we were in different departments, I had numerous opportunities to observe him in his duties as Operations Officer. He was, in my opinion, easily the sharpest, most knowledgeable and competent officer on our ship. He was a positive example to me in my career.

My sincere condolences to his family.

Sincerely,
Raymond Church

Lucky Newfeld

April 13, 2023

College boyfriend and long time dedicated friend, Tom always stayed in touch and cared about me and my family while sharing all of his life stories, his dedication to his family, his sports, his teaching career, and to Patti. My condolences to the family and to Patti. He was a special love and will be missed.

Penny Bach Evins

April 7, 2023

Mr. Generous was and is a role model in ways too numerous to name.

He attended my wedding celebrations, stayed with my family in New Orleans and remained a confidant in my years serving educational communities. My husband and I dined on fabulous Southern food with him in Carrboro just a few years ago.

His love for his family was palpable and his drive to "leave it better" and pay attention to the details allowed thousands of students, advisors, players and colleagues to rise to their potential.

When I first arrived as Choate student, I feared his high bar and did not want to let him down. What I learned was he was educating me, well all of us, to have higher standards for ourselves.

Mr. Generous thank you for your enduring wisdom, humanity and greatness. I am forever thankful for the privilege of knowing you, growing from your fertilization and having the glorious opportunity to call you a mentor and friend.

My thoughts and prayers are with his family.
Love,
Penny Bach Evins '90

David Kennedy

February 3, 2023

Tom was a large and energizing presence in our community here at Stanford during his graduate student days. I was privileged to have him as my teaching assistant, and to serve on his dissertation committee. We became fast friends and managed to stay in touch at least episodically over many decades. I will miss him and extend my heartfelt condolences to his family.

Gail Hearn Capelovitch

February 2, 2023

A finer man you would be hard pressed to find. Tom played such a huge role in my brother Ted's life and mentored him well beyond his time at Choate. A gentleman and a scholar... condolences to the entire Generous family.

Cam Hopkins

January 1, 2023

Doc was one of the most influential people in my life. I was very saddened to learn of his death as he and Diane were truly the reason I chose to attend Choate. They took me in to their lives and home in Pitman House and served as my "second" parents. I will be forever grateful for all of the life, academic and athletic lessons Doc taught me. He will be missed.

Michael Kaufman

December 2, 2022

He was the best, simply the best. Choate 75

Ben Small

November 14, 2022

I was lucky to teach and play squash with Tom for several years at the beginning of my own Choate teaching career. His devotion to the school and its students was legendary and I was amazed by how many young squash players he mentored. Tom was a man with a powerful intellect and he loved sharing it with others; he was a born teacher. My condolences to Suzanne and Michelle - it was a privilege to work with both Tom and Diane.

Jed Peace Friedland

November 14, 2022

Tom Generous was solid as a rock. His compassion, clarity and determination broke me open and provided a much needed foundation to trust others and better myself. I forever treasure the lessons learned from this great man and am forever thankful that he took such an interest in me in my formative years.

Stanley Freedman

November 13, 2022

First, let me express my condolences to his daughters and family.
I spent three years with Tom at Brown (1959-1962). He was the spirit and mayor of Plantations House (the commuters' house)at Brown. What a guy! Friendly, outgoing- just a pleasure to be around- discussing politics, eating pizza, playing cards. Not too many years ago, he communicated with me about learning to play the flute (I was a music teacher). WHat more can I say. May his soul rest in peace.

Michael Gannon

November 13, 2022

We were saddened to read today of Tom's death.
I taught with Tom many years ago, and I respected his many contributions to Choate Rosemary, whether in the classroom, on the athletic field or wherever. He was a gentleman who left his mark for his high standards in everything he touched, and generations of his students will remember his thoughtful teaching. Our condolences to his daughters, their spouses, and grandchildren.

Tom Courage

November 13, 2022

Seymour St. John, former Choate Headmaster, used to say that wherever you are, you should make that place better for your having been there. Few met that test as well as Tom, through his teaching, coaching, chronicling of the school history and just being the type of person that he was.

Marty Pomerantz

November 13, 2022

I loved your dad and how instrumental he was in creating and growing the squash community at UNC. Our greater connection, however, was commiserating over spouses stricken by multiple myeloma. I only hope I might have been of some comfort to him during your mom’s decline.

Your dad was a great, gentle, always interesting and intellectual man who was so proud of his daughters. My condolences to you both.

Roger Breslow

November 12, 2022

My condolences to the Generous family. Tom and I were classmates and fellow commuting students at Brown, and I knew him well. Her was also very active in intramural sports then.

Michael Breed

November 11, 2022

Doc was a man of character, standard, regimen and respect. The lives he impacted are numerous and I’m proud to say he changed my life. Thanks is not enough. RIP my friend

Lexi Street

November 5, 2022

Having briefly known Tom for less than 10 years, he certainly lived up to his name. He was so generous of heart to my mother who absolutely adored him. He was so wonderful and kind to her. I couldn’t be happier that she got to share in his life and be apart of it. Sending comfort and peace to his two lovely daughters.

Amy Rabinowitz

November 5, 2022

I never had the privilege of taking a class or playing a season of squash with Tom Generous, but I credit him as being the teacher who most changed my life. I will be forever grateful for the faculty fundraising effort he initiated that raised enough money for me to be able to attend Choate. His willingness to think differently, search for a solution and lead others to action continues to inspire me to this day. What a great life he led. He will be much missed.

Nancy Aldet

November 2, 2022

Mr. Generous was a wonderful house leader while I was at Choate. Kind, funny and always had his door open. He and his wife made us feel like family. The whole Choate community felt that way which is a testament to what a gem he was. He’ll be missed. Sending love to Suzanne and the rest for his family.

George Stein

November 1, 2022

I vividly remember being fortunate enough to take one of Tom's classes at Choate in 1983-84. His humor, passion and intellect were so compelling; and I remember feeling like "Wow...I could listen to this guy talk all day!" It's a sad day indeed. God needed another angel I suppose...

Robert Dowling

October 31, 2022

Tom and his late wife Diane were wonderful neighbors to us here in Bolin Forest in Carrboro, NC. Tom was a modest guy who was far more accomplished than most of us knew. Despite his recent inability to continue riding his bike, I saw him walking uphill using two ski poles about two weeks ago. Tom was tenacious and he will be missed.

Dan Courcey

October 31, 2022

The sad passing of one of the all-time Choate Rosemary Hall greats. I can say with considerable personal and professional assurance that there are generations of former Choate students - history aficionados (how about that amazing Con Law course!) and squash players - who, when looking back on their time at the School, will cite Tom Generous as the single greatest, most impactful teacher-coach they ever had. Period.

And those fortunate enough to be talentless baseball players on the Choate JV baseball team were accorded the special treat of living/experiencing the spectacle of Tom Generous as a prep school-version of Earl Weaver. A sight to behold.

The only solace in this sadness is that Tom is now joined in loving eternity with the amazing Diane, the blessed beauty to his amazing, intellectually relentless and inspiring-benevolent beast. May he rest in everlasting footnotes, legal precedences and stunning kill shots.

Sending Michelle and Suzanne and their respective loved ones heartfelt condolences and much love. A loss for the ages. There will never be another.

Chip Truwit

October 31, 2022

Sincerest condolences from the first Truwit Tom got to know, although it was the later Truwit's and Trubowitz' that Tom guided to a whole new level of squash. I was a senior as Tom and Diane arrived...essentially their first graduating class. Tom brought great enthusiasm to his classes, his coaching and his role as a "housemaster". He was liked and respected by all.

Rebecca Cushing

October 31, 2022

Please accept my deepest condolence at your loss. I have such strong memories of Mr. Generous, first as the father of two childhood/lifelong friends (his amazing daughters), and then as a teacher in high school. He was smart, honest and funny, character traits both Suzanne and Michelle have inherited. May you both find peace and comfort during this difficult time. Xo Rebecca Cushing (nee Severance)

Sarah Cooke

October 31, 2022

My condolences to the family and gratitude for his true generosity to countless students over so many years.

Michael Rinaldi

October 31, 2022

Our deepest sympathy to Michelle, Suzanne and their families. Tom was a respected Choate colleague and friend and shall be greatly missed by all who knew him. May he Rest In Peace.
The Rinaldi family.

David Aversa

October 31, 2022

Sincerest condolences from the Aversa family. Rest in peace processor. He as a true Choate icon!

Bill and Karen Feinberg

October 31, 2022

Tom was a dear friend and classmate, Ever True to Brown. Our P-House gang will miss him.

Diane Garland

October 31, 2022

Michelle and Suzanne so sorry to hear of your loss. I will always remember your father standing by Diane at gathering that we attended during the Wallingford Junior Women's Club celebrations. Great gentleman.

Emile Toscano

October 31, 2022

Tom, you meant the world to me. You introduced squash to me when I was so young and were there for me every step of the way. You were so kind and caring. You went above and beyond for people in the chapel hill community to introduce squash. I wouldn’t be where I am today without you. RIP Tom.

Charlotte Murphy

October 28, 2022

Terrific guy! Great memories.

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