Shirley Van Meter Freeman, a distinguished figure in Key West’s history as a former Monroe County Mayor, Commissioner, and dedicated educator, peacefully passed away at her Key West home on April 6th, 2024. Her life, shared beautifully with her partner Harvey Server in Key West, was a testament to unwavering community dedication and profound generosity.
Born in 1935 in Marvell, Arkansas, Shirley’s upbringing on a cotton farm instilled in her the values of family and community that would define her remarkable life. She pursued higher education at the University of Arkansas, earning both Bachelor’s and Master’s degrees in Education. Her early career took her internationally, serving as headmaster at the American Embassy School of Zagreb, Yugoslavia, before returning to the US to obtain a PhD in School System Management from Miami University of Ohio.
In 1971, Shirley’s journey brought her to Key West, where she took on roles as principal at Frederick Douglass Public School and Sigsbee Elementary School at the Key West Naval Air Station. Her passion for education and mentorship left a lasting impact on countless students who, even years later, would express gratitude for her guidance and support.
Her life took another significant turn in 1973 when she married William A. “Billy” Freeman, Jr., a prominent figure in Florida politics as a former State Representative, Monroe County Commissioner, and Sheriff. Shirley became an integral part of Billy’s public service, working tirelessly alongside him in his campaigns and community initiatives. Following Billy’s passing in 1989, Shirley continued the Freeman legacy of public service by entering politics herself. She was elected Monroe County Commissioner, serving with distinction for eight years, including three as Mayor. Her contributions, alongside Billy’s, were permanently honored in 2009 with the naming of the Freeman Justice Center in Monroe County.
Shirley was a passionate advocate for environmental protection, deeply committed to preserving the delicate ecosystem of the Florida Keys. She championed the protection of Key West’s waterfront and its historic neighborhoods, always striving to do what she believed was right for her community, the state, the nation, and the planet.
A new chapter of love and companionship began in 1996 when Shirley met Harvey W. Server, a retired real estate developer from Chicago. Their life together in Key West blossomed, marked by a shared commitment to philanthropy and community engagement. Shirley and Harvey became a well-known and admired couple in Key West, opening their historic old-town home to host numerous non-profit organizations whose missions they passionately supported. This Key West home, a backdrop to their shared life, became a hub for charitable work and community gatherings.
Shirley’s dedication to mentoring, particularly women in politics, was evident in her active involvement with organizations such as the Community Foundation of the Florida Keys, the Key West Zonta Chapter, the National Organization of Women (NOW), and the League of Women Voters. Her support extended to the Florida Keys Democrats, the Florida Keys Council of the Arts, Last Stand, the Salvation Army, the Woman’s Club, and the South Florida Symphony Orchestra. Through the Community Foundation, she and Harvey Server established the Shirley Freeman and Harvey Server Environmental Fund, further cementing their joint commitment to conservation in the Keys.
In 2017, Shirley’s lifelong dedication to service was recognized when she was named Humanitarian of the Year by the American Red Cross. She also contributed her insights to the Key West Citizen’s editorial board and served on the Boards of the College of the Florida Keys, the Tourist Development Council, and the Florida Board of Bar Examiners. Whether it was a large organization or a local cause, Shirley consistently sought ways to contribute and make a difference.
Beyond her public service, Shirley was an accomplished pianist with a deep love for music and the arts. Her daily piano ritual with Harvey brought them immense joy, and they were enthusiastic supporters of Key West’s vibrant arts scene, regularly attending performances at the Waterfront Playhouse, Red Barn Theater, and the Symphony at the Tennessee Williams Theater.
Shirley was predeceased by her husband William A. “Billy” Freeman, Jr., and his children William A. Freeman, III, and Julie Ann Freeman Spilker.
She is survived by her beloved partner, Harvey W. Server of Key West, her sisters LauraLee Rogers-Tinkle, Janet Hill, and Hope (Lynn) Hallum, her brother, Ike M. (Christine) VanMeter, brother-in-law, David W. (Elizabeth) Freeman, son, James Curry Freeman, daughter-in-law, Brenda Freeman, and numerous grandchildren and great-grandchildren. Her family was the center of her world, and she cherished her roles as daughter, sister, matriarch, and grandmother.
Shirley Freeman’s legacy in Key West is one of profound impact, characterized by her love for her community, her compassionate spirit, and her unwavering support for those around her. Her life, particularly her shared journey with Harvey Server in Key West, serves as an inspiration for kindness and dedication.
A celebration of Shirley’s life will be held at Williams Hall, 729 Fleming St, Key West at 5 PM on May 14, 2024. In lieu of flowers, the family requests donations to the Community Foundation of the Florida Keys for the Shirley Freeman and Harvey Server Environmental Fund, continuing her and Harvey’s shared commitment to the environment they both cherished in Key West. Funeral arrangements are being handled by the Key West Mortuary.
As Key West bids farewell to Shirley Freeman, her remarkable life and the positive changes she brought to her community will long be remembered. Her spirit, intertwined with the memories of her life with Harvey Server in Key West, will continue to inspire acts of service and a deep appreciation for community.
Rest in peace, dear Shirley.
