Sally Deegan — for many years the secretary to the principal of Staples High School, and part of a long-time, well known Westport family — died earlier this month. She was 93. Her family writes:
Our mother, Sally J. Deegan, passed away after a valiant battle with old age.
She was born May 28, 1926 in Ridgefield, to Marion Wakeman and Sereno Thorp Jacob. Her dad was a pioneer aviator who flew in The Lafayette Escadrille during World War I.
As a child, Sally battled numerous life-threatening illnesses and missed a lot of school. However, her determination to succeed at everything she did, saw her through. She graduated from Ridgefield High School as class valedictorian.
A child of the Great Depression, after high school she went right to New York City, and was hired as secretary to the president of Faberge Perfumes. Fable has it she was taking dictation while watching a plane crash into the Empire State Building.
In 1946 she married our dad, Donald B. Kellogg. They lived at Compo Beach. Don passed away several years after their 4th child was born, leaving Mom a young widow with 4 kids under the age of 13. She drew on her warrior spirit, doing what she had to to keep a roof over our heads and food on the table.
Not long after she met the love of her life, William F. Deegan. They married in 1962. He had the courage to take on 4 kids, and survived our teenage years. Bill was a crack golfer so Mom, drawing again upon her tenacious spirit, learned how to play.

Sally Deegan
After summers spent on Fairfield Beach, they pursued their dream of having a home in Vermont. They joined the Woodstock Country Club, where Mom won the club championship and chaired the women’s golf committee.
Before moving to Vermont permanently, Mom was secretary to several principals at Staples High School in Westport. No student wanted to be confronted by her.
She also formed the union for public school staff that provided health insurance benefits. She was brilliant at reading fine print, and learning the ins and outs of the insurance industry, which served her for the rest of her life.
Bill and Mom enjoyed many years in Woodstock. They played lots of golf, and made many friends. Bill passed away in 1997.
Before moving to Naples, Florida in 2001, Mom worked at The Bank of Woodstock, and was a part-time realtor.
Mom loved her hard-earned retirement years in Naples. She enjoyed lots golf, tennis, bridge, and many new friends. She played golf just before her 90th birthday, and had a wicked short game. However, old age crept up. Her final years were spent at Aston Gardens Senior Living, where she made even more friends.
Our mom was a Valkyrie. She had gumption and grit. She was smarter than most, and her intuition never failed her. Saint Peter better have his office in order, because she will see to it that his filing system is in order, and his desk clean.
She is survived by her brother, Merritt W. B. Jacob of Hendersonville, North Carolina; children Sally Kellogg (Bruce Tansey) of Naples, Florida, William Bradley Kellogg of Fairfield, Hope Kellogg Kokas (Dan) of Holderness, New Hampshire, and Donald B. Kellogg, Jr. (Anthony Arguelles) of Providence, Rhode Island, and step-daughter Sharon Deegan.
She will be missed as well by her 5 grandchildren and 7 great-grandsons. She was Aunt Sally to the Jacob girls, residing in Connecticut and Newport, and their brother. Finally, she will be missed by her beloved cat Casper.
We will be forever grateful to Jessica Anderson for her dedication to Mom’s comfort and care for the past 6 months; the folks at AVOW Hospice, and all the staff at The Inn at Aston Gardens.
Internment will take place in Westport. In lieu of flowers, please send a donation to The Humane Society of Naples or The First Tee Naples/Collier.
To Sally Deegan’s family- my condolences to you all!
I think of your Mom often as I remember the beautiful things she used to knit, I knit too! I loved the sea glass she collected and put in glass jars in the windows in the upstairs porch . I also remembered her crocheted bed spread with the covered blanket underneath. I thought it was so pretty when I was young, that as an adult I bought a crocheted table cloth and put another colored cloth underneath for a holiday table setting. Peachy, Brad, Hope and DB, I’m sorry for your loss of your Mom!
Oh Vicki! Where are you living? I loved keeping up with your Dad on 06880. We were so lucky to grow up on Roosevelt Road at Compo.
I’m so sorry to hear this news..My condolences, Dave Eason
Vicki, thank you for your memories and condolences! Last week cleaning out mom’s apartment, we found more sea glass from LI Sound! And of course she was constantly working on crocheting, and left a knitting project of which I will finish. Your parents have been in my thoughts, especially since your dad’s passing. Both sets of parents lived through interesting times for sure! You can move away, but you can’t take away our childhood memories of growing up on Roosevelt Road by the beach!
Beautiful ❤️
Condolences to you Sally – losing a mom is such a time marker, and one always misses her. (MGHorelickGristina)
Sally was a force within the Staples community. She kept principals on their toes and was not afraid to let them know that they had made mistakes.Smart and committed, she made the school a better place in which to learn
Thank you so much…Mom would have so appreciated your observation(s). She was a pistol.