James Fiore

James J. Fiore

February 13, 1939 – July 21, 2026

James J. Fiore, devoted husband, beloved father and Grandpa, known to friends and family as Jim or Skip, died July 21, 2026 at the age of 87.

Jim was born February 13,1939 in Oswego, New York. Due to circumstances beyond his family’s control, he spent his early childhood in an orphanage. When he was eight, his mother and newly adoptive father were able to bring him and his siblings home. After graduating from Jamesville-DeWitt High School in 1957, Jim headed to the University of Notre Dame where he enjoyed rooting for the Fighting Irish as a member of its all-male cheerleading squad. Jim graduated in 1961 with a BA in History and maintained a lifelong connection to his alma mater.

Following college, Jim joined the Navy and, after graduating from Officer Candidate School in Newport, RI, served on the Fleet Air Wing staff at the Barbers Point Naval Air Station in Oahu, Hawaii until 1964. In 1962, Jim married Barbara Hipp. They adopted two children, Karen and Michael, and remained married until 1983.

After the Navy, Jim pursued a career in banking. He spent four years in Chicago at Continental Illinois National Bank and Trust Co., attending graduate school in the evenings. In 1968, the family moved to Madison, Wisconsin where Jim became a Vice President at First Wisconsin National Bank. The pinnacle of Jim’s banking career came between 1976 and 1986 when he was President, CEO and Chairman of the Board at Randall Bank on Monroe Street. Jim took great delight and found deep satisfaction in helping Randall’s clients achieve their business and personal dreams. He also took pride in developing and mentoring a dedicated, highly competent staff.

Jim was always on a mission to improve things. His talent for quickly grasping complex situations and finding practical solutions and his natural leadership abilities underscored his long history of public and private service. He served on the Madison Metropolitan School Board from 1975 – 1977, and on the Board of Trustees for Edgewood College from 1979 through 1998, including two terms as chairman of the Board. An avid golfer and long-time member of Nakoma Country Club, Jim served on Nakoma Golf Club’s Board of Directors from 1982 - 1987, and as President in 1986. Jim also served six years on the Board of Funds and Endowment for the Episcopal Diocese of Milwaukee, including two terms as President.

1986 brought big changes for Jim. He married Susan Chapman and became stepfather to her two sons, Matthew and Andrew Dregne. Associated Bank also acquired Randall Bank. Although Jim stayed on an additional eight years, the corporate overlay changed the nature

of his work, and he missed the independence and ability to nurture community that he had enjoyed as the leader of Randall Bank. In 1994, he chose to retire from banking.

After he retired, Jim and Susan bought and renovated a home on 12 wooded acres. Through big windows they enjoyed watching woodland critters and plant life through the ever-changing seasons. In 2016, Jim and Susan donated 9 of their 12 acres to the Ice Age Trail Alliance so it could remain undeveloped and be enjoyed by others. Jim and Susan enjoyed traveling and Jim enjoyed golfing and his regular Thursday night dinners with Nakoma buddies. Although retired, Jim never let grass grow under his feet. He was happiest and most engaged when working to solve problems and help others achieve their dreams. After retiring, Jim channeled his considerable energy and talent into helping his family across all generations -- parents, children and grandchildren. He was a generous, proactive, creative and steady leader – never micromanaging or interfering but always working the “problems” of how to improve the lives of those he loved. He never wavered from The Golden Rule, always treating others as he would want to be treated.

Jim and Susan were married for 38 years. When Susan’s health declined and until her death in 2024, Jim devoted all his energy to her care and wellbeing. His foresight, love and guidance through the years left his family in a far better place than they would have been without him. He was deeply loved and will be sorely missed.

Jim was predeceased by his wife, Susan Fiore; mother Hazel (Thompson Fiore) Haug and her husband Otto; father James L. Fiore; sisters Barbara Chamberlin and Marilynn Goode; and brothers-in law Marty Chamberlin and Jerry Goode.

Jim is survived by his children, Karen Olson (Richard) and Michael Fiore; stepsons Matthew (Claire Silverman) and Andrew (Andrea) Dregne; grandchildren Noah and Olivia Dregne, Annika and Erik Olson, Bodie Fiore; brother-in-law Steven Chapman (Cindy Kelm); and many nieces and nephews.

In lieu of flowers, those wishing to donate in Jim’s memory might consider one of Jim’s favorite organizations: Edgewood College, American Players Theatre, or St. Andrew’s Episcopal Church.

Jim’s burial service will be private, according to Jim’s wishes, and family and friends will celebrate his extraordinary life at a later date to be determined.

To view his obituary and leave a memory, please visit: www.ryanfuneralservice.com


Ryan Funeral Home & Cremation Services
Verona Chapel
220 Enterprise Drive
608-845-6625