Dorothy P. Shields

Dorothy “Dori” Shields, a vibrant and unconventional soul, passed away in Venice, FL on May 31, 2025, at the too-young age 78, following a brief illness.

 Dori was born on December 13, 1946, in New Britain, CT to the late Mary Nirosky Shields and Michael Shields. She held a Juris Doctor from Whittier College in Southern California and went on to embark upon a long and successful career in the insurance industry.

 Dori was a force of nature and, in the “old boys” network of insurance, rose to be head of Personal Insurance for Travelers in Los Angeles. Subsequently, she co-founded Casswood Insurance which became the premier insurer-of choice in the areas of film and television production, celebrity coverage, and Pride events nationwide. In addition to her professional accomplishments and keen intelligence, Dori was known as shrewd poker player, an impish Irish teller of tales, and someone who could be counted upon to show up with a smile on her face and joy in her heart. She made her way through life with no enemies, no regrets and an indomitable spirit which sustained her to the very end.

 In 2017, Dori and her beloved wife, Caryl, relocated from Saratoga Springs, NY, to Venice, FL leaving behind Caryl’s family’s seasonal golf course for many sunny, year-round courses in SW Florida. Dori loved the game of golf. On their first outing Caryl beat Dori but that was a feat never to be repeated. 

 Eventually, Dori and Caryl were surrounded by innumerable friends and supporters, and those closest to them became integral to their lives, including a whole new group of poker players (and casinos) that were always happy to see Dori’s face at the table. In fact, most recently she was elated to have won $200 in an online game from her hospital bed! Dori and Caryl were committed to rescuing senior Golden Retrievers and, most recently, Dori served as President of her HOA board, thus adding yet another accomplishment and act of service to the tapestry of her life. Dori enjoyed an enduring community of friends nationwide who will continue to cherish Dori’s memory.

 In addition to her wife, Dori is survived by her sister Marge Wisk (Bill), sister-in law Arlene Shields and mother-in-law Patricia Shakshober, nieces Mary Ann Pixton (Phil), Karolin Palko (Bob), Kathy Elliott (Dave), Katie Greenwalt and nephews Bill Wisk, Jr (Jodi), Rob Shields (Lindsay) and Michael Thomas Shields (Dawne) and many great nieces and nephews. She was predeceased by her brother Michael Shields.

Donations in her memory may be made to the Golden Retriever Rescue of SW Florida, PO Box 368186 Bonita Springs, FL 34136 or The Suncoast Humane Society, 2620 Worth Ave., Englewood, FL 34224.

In the alternative, the family suggests enjoying a Klondike Bar with an eye towards Heaven; Dori will be smiling down. Farley Funeral Home in Venice is handling the arrangements. To send a condolence please visit www.farleyfuneralhome.com.