Samuel Holloway

Samuel Norris Holloway, Sr., of Gainesville, Florida, passed away at the age of 90 on January 15th, 2026.

Sam’s commitments to work and service were exceeded by his love for his family. He was a devoted, wonderful husband. As a father, he taught by example and by words of wisdom. Sam lived according to sterling qualities of integrity, kindness, humility, generosity, humor, and gentlemanly courtesy, an inspiration to all who knew and loved him. He will be remembered with abiding love.

Sam was born on November 6, 1935, the tenth of eleven children, in Jacksonville, Florida, to Jean O’Leary Holloway and Luther William Holloway, M.D. He was raised in Jacksonville and graduated from Robert E. Lee High School and Jacksonville Junior College. He transferred to Stetson University and completed a B. A. degree in History in 1957.

In 1958, Sam married his one love, Connie Bishop of Gainesville, Florida. Late that year, the couple moved to Ayer, Massachusetts, after Sam’s commission into the U.S. Army, where he served in the Military Intelligence Corps until 1960.

That year, Sam and Connie returned to Gainesville following the birth of their first child. In the next four years, three siblings joined her. Sam balanced fatherhood with pursuing his career, beginning with Liberty National Life Insurance Company and continuing with Northwestern Mutual Life Insurance Company (NML). Sam eventually became the NML District Agent in Gainesville and later, he launched his own company, Holloway Financial Services, Inc., which he headed until retirement in 2014.

The University of Florida was important in Sam’s life. For more than 30 years, he was the Agent of Record for the College of Medicine’s benefit programs. He supported other programs at U. F. Health, such as the Stem Cell Research Facility, and was a founding director of Oak Hammock Retirement Community. Sam sponsored productions at the Phillips Center for the Performing Arts, was in the Quarterback Club, and was an avid Gator fan.

Over the years, Sam was active in the Gainesville Association of Life Underwriters, Gainesville Plan Board, and Gainesville Chamber of Commerce. He was a director on several bank boards, a long-time member of the Rotary and Kiwanis Clubs, and he furthered the mission of the Family Practice Group. As a congregant and on the Vestry, he served Holy Trinity Episcopal Church, then Trinity United Methodist Church.

In his spare time, Sam was active socially and enjoyed playing golf at the Gainesville Golf and Country Club and at Wildcat Cliffs Country Club in Highlands, North Carolina. His interest in history and in other cultures led him and Connie to travel to interesting places.

Sam was preceded in death by his parents, sisters Pearse Freel, Jean Bein, Betty Sanderson, Penelope Fitzgerald, and Catherine Holloway; and brothers Bob Holloway, John Holloway, and Luke Holloway.

Sam is survived by his brothers Larry Holloway and Mike Holloway; his wife of 67 years, Connie; children Judy Boucias (Drion), Wilbur Holloway, Jean Robinson (Tommy), and Sam Holloway, Jr. (Carrie); grandchildren Remy Boucias (Sara Schiavone), Byron Boucias, Zach Boucias (Tiare Contador), Katy Robinson, Matt Robinson, Caroline Cohen (David), and Jack Holloway; and great-grandchildren Sam Cohen, Charlotte Cohen, Alice Cohen, Bruno Boucias Contador, Galo Boucias Contador, and numerous other relatives.

All of us are immensely grateful to have shared our lives with Sam for as long as we did. He will live on in our hearts and continue to light our lives.

Sam’s Celebration of Life will be in the Tower Club Ballroom at The Village, 8000 NW 27th Blvd., Gainesville, at 11:00 a.m. on January 24th, 2026.

In lieu of flowers, please donate to The Foundation of Community Hospice and Palliative Care at thefoundationcares.org/give.