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Whit Sheppard ’83 has passed

Whitney Clark Sheppard

Whit Sheppard, 59, died peacefully on December 27, 2023, at Greenwich Hospital, after a bravely-fought battle with melanoma.

Born in New York City on December 8, 1964, Whit was the beloved son of Linda C. Waterman, the late Christopher R. Sheppard, and the late Mike Waterman.

Whit moved to Greenwich as a very young boy, and attended the Greenwich Country Day School and Brunswick. He graduated from Deerfield Academy, Southern Methodist University, and also earned an MBA from the University of Texas and a master’s in journalism from the University of Oregon. With his brilliant mind and insatiable passion for travel and adventure, Whit wore many hats and enjoyed stints in New York, Dallas, Austin, Eugene, Taos, Paris, Melbourne, Richmond, Boston, and Greenwich.

French teacher, ESPN journalist, Morgan Stanley analyst, Boston College tennis coach, and independent school advisor were among Whit’s many professional roles. Whit was also very involved in the recovery community and served as a sponsor and mentor in Alcoholics Anonymous for nearly forty years, lifting up those struggling with addiction and touching many lives.

All who knew Whit would agree that far and away his greatest and proudest role in life was being an incredibly devoted father to his amazing daughter, Emily Vaughan Sheppard. Whit and Molly Taylor Sheppard shared their daughter, Emily, with love and grace, even after divorcing many years ago. Nothing brought Whit more joy than spending time with Emily, whom he adored beyond measure. He especially loved sharing his passion for travel with her as they created incredible memories together, exploring Australia, South Africa, Mauritius, Anguilla, Mexico, the UK, and France, on their epic father-daughter adventures.

Whit was a bibliophile, rackets enthusiast, golfer, dog lover, foodie, linguist, and globetrotter. He had a great sense of humor and loved words, cultures, languages, animals, and babies and children of all ages. Whit was a gentleman, charming and kind, old-school. He loved a good meal, a great book, tide rides in Martha’s Vineyard, a fresh croissant, chai tea lattes, and playing tennis, paddle, and squash. Ever handsome with a twinkle in his eye, Whit will be sorely missed.

In addition to his daughter, Emily Sheppard, mother, Linda Waterman, and ex-wife, Molly Sheppard, Whit is survived by his brother, Neil Waterman and sister-in-law, Jen Waterman, his sister, Brooke Stahl and brother-in-law, Ryder Stahl, and many adoring nieces, nephews, cousins, aunts, uncles, friends, and his beloved rescue dog, Auggie.

In lieu of flowers, please consider a donation in Whit’s memory to the Melanoma Research Foundation ( melanoma.org ) or to the ASPCA ( aspca.org ).

Ed. Note: So gratefeul that Whit (l) attended our 40th reunion…

Frequently Asked Questions

Upon graduating from Deerfield, alumni enter a diverse network of former Deerfield students. Deerfield alumni have ventured into almost every area of employment, and many are at the top of their respective fields. The advantages of this vast network are numerous and significant, as every member of the Deerfield family receives the following:

Alumni are also eligible for alumni awards, such as the Ashley Award, Heritage Award, and the Mimi Morsman Award.

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