Thomas H Gillespie, Jr.
August 21, 1933-April 25, 2023

Thomas Howard Gillespie, Jr., a 55-year resident of New Canaan, CT, died on April 25, 2023. He was born in Chicago, IL on August 21, 1933, a son of Thomas Howard and Florence Stoker Gillespie, and raised in Kenilworth, IL. As a youth attending Joseph Sears School and New Trier Township High School, Tom was active in sports and achieved his Eagle Scout rank in Boy Scouts at the early age of 13. Tom graduated from Cornell University, Class of 1955. He was an active member of the Sigma Phi fraternity in college and for more than 60 years thereafter. Drafted into the Army following college, Tom served primarily in the Signal Corps in the Philippines.

Following his service, Tom attended the Northwestern Graduate School of Business (now Kellogg), receiving his MBA in 1960. That same year he moved to San Francisco to begin a career in investment management. He met his beloved wife of 43 years, Josephine, during his first week in San Francisco. Jo and Tom were married soon after and moved east in 1965. After achieving CFA certification in 1966, Tom co-founded the predecessor to Gillespie, Robinson & Grimm, an investment firm that he led for 49 years before his retirement in 2020 at age 87.

Tom moved to New Canaan in 1968 and lived in the same house for the remainder of his life. Tom was a generous supporter of national and local causes and served on the boards of the United Way, Woodway Country Club (of which he was a member for 50 years), The New Canaan Inn, and the Congregational Church of New Canaan.

Tom always believed he led a blessed life. He could find someone he knew from his past almost anywhere in the world. He was always active, including skiing on the National Ski Patrol, shooting river rapids in a canoe, and playing golf all over the world. An avid traveler, Tom covered most of the globe and won the family’s 50-State Challenge. While later in life he could be found enjoying a good book of historical fiction and sipping his favorite “Scottish wine” (aka Scotch), he continued to travel the world into his late 80s. Tom was a kind and generous man, with a keen sense of right and wrong. He had time and a story for people from all walks of life, but his family was his focus, with his eight grandchildren the collective apple of his eye.

Tom is predeceased by his wife Josephine Bunch Gillespie, his parents Thomas and Florence Gillespie, and his brother Robert Alexander Gillespie. Tom is survived by his three children and eight grandchildren, including his son Thomas (wife Mary, children Shea, Josie, Trip) of Great Falls, VA, his son Douglas (wife Serena, children Alexandra, Douglas) of New Canaan, CT, and his daughter Allison (children Ryan, Lindsay, Graham) of Atlanta, GA.

A service was held on Sunday, May 21 at the Congregational Church of New Canaan, with a reception immediately following at Woodway Country Club. In lieu of flowers, donations may be sent to the Congregational Church of New Canaan.