William J. McCaffrey, 70, a longtime resident of Rye, passed away peacefully on May 26, 2023, following a valiant battle with cancer and congestive heart failure. 

Born in New Rochelle, New York, on December 17, 1952, he was the son of John and Barbara (Porter) McCaffrey, both New Rochelle natives. The middle child in a family of five boys, Bill spent nearly all his young life in the house on Mt. Joy Place, growing up alongside his brothers John, Mike, Pat, and Bob. After graduating from Blessed Sacrament High School in 1970, he attended Westchester Community College and Fordham University. 

In 1976, Mr. McCaffrey launched a highly successful career in the advertising industry, which included executive positions at some of the most renowned agencies of his generation, including Young & Rubicam, Grey Advertising, and Chiat/Day, as well as the formation of his own account planning and consumer research consultancy. 

In 1985, he met Mary Gerspach at a marketing research company’s holiday party in midtown Manhattan, when Mary’s friend dared her to ask Bill to dance. They were married on November 28, 1992. 

He loved his annual Cape Cod vacations – a McCaffrey clan tradition dating back to his infancy, Giant game tailgates, and any excuse for a good party. He firmly believed that even a cloudy day at the beach was better than a day anywhere else. He will be remembered for his sense of humor, his wit, and his big, big heart. 

In addition to Mary, his wife of 30 years, he is survived by his brothers, John (Kathy), Mike (Arlene), Patrick (Diane), and Bob (Clare), as well as his brothers-in-law John (Dori), Tom (Eileen), and Jim (Cathy); his 20 nieces and nephews and their children, and many, many cousins, and good friends – all of whom he loved beyond measure. 

A Mass of Christian burial will be celebrated at Church of the Resurrection June 2 at 10 a.m. 

The family kindly requests donations be made to Memorial Sloan Kettering or Calvary Hospital & Hospice.