Josephine Ann Raimondi of Westport, CT passed away peacefully at her home on Sept. 10, 2026. She was born on Dec. 3, 1957, the cherished daughter of Anthony and Catherine Raimondi of Indianapolis, Indiana. Josephine grew up in Indianapolis where she enjoyed the benefits of being a part of a large, extended Italian family and the “benefits” and constraints of having six brothers!

Josephine valued education. She graduated from Georgetown University’s School of Business, started working at a Chicago area accounting firm, and soon acquired credentials as a CPA.. She furthered her education by then attending the University of Michigan and earning a law degree. She enjoyed a distinguished legal career, spending 30 years with W. R. Berkley Corporation and retiring in January 2023 as Vice President-Senior Counsel.

Josephine lived in Westport, Connecticut, for most of her adult life and valued the many connections formed there. She was a longtime member of St. Luke Roman Catholic Church and the St. Luke’s Women’s Club. She was deeply involved with the Women’s League of Westport, where she served as president from 2005–2006 and volunteered for many years. She was active with the Westport Senior Center as well. 

Josephine loved spending time with family and friends. She was especially devoted to her nieces, nephews, grandniece and grandnephews and took great pleasure in being part of their lives. She cherished her friendships and had a wonderful circle of friends in Westport. Among them was a group who gathered every Saturday morning for coffee at Panera or, when the weather cooperated, at the beach. For family, friends and co-workers, Christmas simply wasn’t complete without a package of Josephine’s homemade butter cookies and moscotti. Her holiday baking was a beloved tradition and one of the many ways she shared her love with the people around her. 

Josephine had a lifelong appreciation for the arts. She enjoyed attending local art shows and making trips to New York City for theater. International travel was another great passion. One particularly meaningful journey was a pilgrimage to Italy last year with members of her parish church.

Josephine lived a life of profound faith. Her church, faith community and prayers were touchstones of her daily routine. She will be remembered for her intelligence, independence, curiosity, generosity of spirit, and her ability to create and maintain lasting friendships.

Josephine is survived by her brothers, Mike (Patty), Anthony (Ellen), Mark (MB), and Joe (Laura), along with 11 nieces and nephews and five grandnieces and grandnephews. She was predeceased by her parents, Anthony and Catherine Raimondi, and her brothers Cosmas and John.

Visitation will be held on Tuesday, Sept. 22 from 4-7 p.m. at the O’Riley-Branson Funeral Home, 6107 S East Street, Indianapolis. A funeral mass will be celebrated at St. Mark Church, 535 E Edgewood Ave., Indianapolis on Wednesday, Sept 23 at 10 a.m. with interment to follow. A mass in Josephine’s memory will also be celebrated in Westport, Connecticut, at St. Luke Church, 49 Turkey Hill Rd. North, on Tuesday, Oct. 20 at 11 a.m. with a celebration of life reception to follow. 

In lieu of flowers, please consider donating to either of the following charities in Josephine’s memory: 

Little Sisters of the Poor, Indianapolis, 2345 W. 86th St, Indianapolis, IN 46260 or online.
Women’ s League of Westport, 606 Post Road E., Box 512, Westport, CT 06880 or online.

Josephine will be deeply missed by her family, friends, and the many people whose lives she touched. She leaves behind a lifetime of friendships, experiences, and memories that will be treasured by all who knew and loved her.