an older woman holding two plaques in her hands
Zonta Club of Key West, which Shirley Freeman founded in 1981, honored her in 2022. ROBERTA DePIERO/Contributed

Shirley Freeman was born and lived much of her life in what she ruefully called “a man’s world.”

On April 6, she left behind a much different world  — one she had helped to change — when she died at the age of 89.

She was Shirley Van Meter when she arrived in 1935 in a tiny Arkansas town during the Great Depression. But she was destined for faraway places, having always studied with yearning the pull-down maps that used to hang above the blackboard in every classroom in every school.

A dedicated student with an insatiable curiosity about the world around her and the people in it, she graduated from college and earned a master’s degree in education from University of Arkansas.

“After teaching for eight years in Arkansas, she applied to overseas embassy schools in Rome, London and Paris. She ended up in Zagreb, Yugoslavia (now Croatia), and took a position as headmaster of the American School,” according to a 2019 tribute compiled by the Lower Keys League of Women Voters. “After two years she returned to the United States to pursue her doctorate in international education and school management from Miami University in Ohio, where she also taught undergraduate courses. She has taught every grade level from kindergarten to graduate school” and lived throughout the United States, including San Francisco, Denver, Washington, D.C. and ultimately, Key West.

Having always noted the map dot called Key West on those classroom maps, and wondering what life must be like there. Van Meter applied in 1971, “basically out of curiosity” for a job as principal of the newly integrated Frederick Douglass School in Key West. Former superintendent Bookie Henriquez flew her to town from Ohio for an interview and hired her on the spot.

The rest is history.

A blind date in Key West introduced the Key West principal to Billy Freeman, for whom the county’s 2008 courthouse, the Freeman Justice Center, would be named.

But back in 1972, Billy Freeman, whose family owned the Porter-Allen Insurance Co. in town, was just wrapping up a 20-year stint as a Monroe County commissioner. A substitute teacher named Frances Signorelli (her husband, Louie, opened Louie’s Backyard) became friends with Shirley and wanted her to meet her husband’s friend, Billy.

The two married in 1973 and soon after, Billy Freeman was elected state representative. After a two-year term, he successfully ran for sheriff and set to work cleaning up the Monroe County Sheriff’s Office amid corruption and drug scandals.

“We had discussed me running for office after he retired as sheriff and I retired from education,” Shirley Freeman said in 2017. “I had been thrust into public life as soon as I met Billy, so everyone knew me as his wife, but I wanted to get to know them on my own.”

And she did. But she had to do it without her husband by her side. Billy Freeman succumbed to lung cancer in 1989, months after finishing his term as sheriff. 

Shirley Freeman continued to fulfill their plans and won her first county commission election in 1992, becoming the county mayor and serving for two terms until 2000.

She met real estate developer Harvey Server in 1995 and the two became supportive sweethearts until the day she died, rarely seen without each other.

Her so-called retirement from education and public office didn’t slow Shirley Freeman at all. 

She was instrumental in leadership roles with Zonta service club, the Key West Woman’s Club, the Red Cross, Lower Keys League of Women Voters, the Community Foundation of the Florida Keys and the Arts Council, to name but a few. She also sang with the Keys Chorale and at times performed on stage for various fundraisers.

In 2010, she bravely posed for Erika Biddle’s tastefully risque “Women Sustaining the Earth” calendar featuring semi-clothed, mature women of the Keys, a fundraiser for the local community garden that was photographed by Carol Tedesco, who recalled the calendar in a Facebook tribute upon Freeman’s passing.

“Each model shared a favorite quote on the subject (of nature, sustainability and the Earth),” Tedesco recalled, adding that Freeman chose a quote by Wendell Berry: “Whether we and our politicians know it or not, Nature is party to all our deals and decisions, and she has more votes, a longer memory, and a sterner sense of justice than we do.”

Tedesco wrote, “So intelligent and engaging, time in her presence was always time VERY well spent. Bon Voyage, Shirley. You left quite a legacy.”

And while Shirley Freeman more than made her mark in what she called “a man’s world,” she was a classy woman until the very end.

Mandy Miles
Mandy Miles drops stuff, breaks things and falls down more than any adult should. An award-winning writer, reporter and columnist, she's been stringing words together in Key West since 1998. "Local news is crucial," she says. "It informs and connects a community. It prompts conversation. It gets people involved, holds people accountable. The Keys Weekly takes its responsibility seriously. Our owners are raising families in Key West & Marathon. Our writers live in the communities we cover - Key West, Marathon & the Upper Keys. We respect our readers. We question our leaders. We believe in the Florida Keys community. And we like to have a good time." Mandy's married to a saintly — and handy — fishing captain, and can't imagine living anywhere else.