When she was growing up, Lee Ann Holroyd never felt a burning calling to become a police officer. While attending the University of Florida, she studied journalism. Writing, she said, was kind of her “thing.”
But fate and circumstance took the Coral Shores High School graduate down a different career path.
Upon returning to the Keys after college, Holroyd landed a temporary job with the Monroe County Sheriff’s Office. Little did she know at the time, that “temporary” job would end up changing the course of her life.
“I took a temporary position as a secretary, when you could still say secretary. I don’t even know if you can still say secretary now,” said Holroyd with a laugh.
It wasn’t until Holroyd was offered permanent employment, as a detective’s assistant, that the desire to pursue law enforcement as a career took hold. She enrolled in the police academy in 1987. Sheriff Rick Ramsay was in her class.
“I knew pretty early on that his goal was to be the sheriff and he knew pretty early on that I wanted to be part of his command staff,” recalled Holroyd.
Fast-forward 41-1/2 years after her humble beginnings as a temporary secretary and MCSO Maj. Lee Ann Holroyd is celebrating her retirement; July 8 was her last day. As a retirement gift from the sheriff’s office, Holroyd was awarded a glass display case with embroidered badges from all of the divisions she worked in throughout her four decades and the distinguished ranks she achieved.
From patrol officer to patrol sergeant to school resource officer to school resource officer supervisor, the ambitious and energetic police officer quickly rose through the ranks.
She was a detective and detective sergeant and the commander of special operations. She spent 18 years on the sheriff’s office dive team. She oversaw the federal narcotics money and laundering taskforce, which took her to places like England and the Channel Islands.
“Just phenomenal opportunities,” said Holroyd of her MCSO career. “I’ve traveled the world from our little hometown here. I’ve traveled all over the world.”
Most recently, Holroyd oversaw internal affairs and professional standards.
Somehow, during her spare time over the years, she managed to earn a dual-major master’s degree in criminal justice and corrections and rehabilitation.
“She’s one of the most well-rounded people I know,” said Ramsay. “She’s an amazing woman. She’s done so much in a very male-dominant job.
“It’s been challenging for women in law enforcement for years to achieve a certain level and she’s one of those people who has been able to break down those walls to prove herself.”
As a woman in the sheriff’s command staff, Holroyd undoubtedly shattered glass ceilings.
“She’s a hard worker and an example for young women in our community, too,” said longtime friend Gina Boilini. Boilini vividly remembers being in middle school when Holroyd was a school resource officer teaching the Drug Abuse Resistance Education (D.A.R.E.) program.
“She was a role model,” recalled Boilini, who now considers Holroyd one of her closest friends.
Another person who describes Holroyd as a mentor is MCSO Capt. Spenser Bryan. Bryan oversees Key Largo and Tavernier for the sheriff’s office. The two go way back. Holroyd has known Bryan since he was born.
“When he came out of the hospital, I actually drove them home. I still carry his baby pictures,” said Holroyd with a smile.
Bryan is going to miss the daily interactions with his colleague and friend, especially when it comes to her level-headed and enthusiastic approach to the job and to life in general.
“She’s non-stop, she’s always going, she makes me tired and I’m younger than her,” said Bryan. “She’s very energetic and probably passionate is the best word to describe her,” he added.
Longtime friend Trish Biondoletti said Holroyd was able to achieve something so many in the workforce can find extremely difficult, a healthy work-life balance.
“She has managed to prioritize her family, friends and community while giving 100% to MCSO. She is truly one of a kind and I am proud to call her my best friend,” said Biondoletti, who has known Holroyd since the 1980s.
For the last nine years, Holroyd has been living in Key West during the week to be close to MCSO headquarters on Stock Island. She would return to her home in Islamorada on the weekends to spend time with her husband, Geno, and special needs adult son, Matthew.
“After nine years, I really missed being home with my family. I’m an Upper Keys girl,” said Holroyd.
One thing is undeniable; there will be no sitting around during retirement for Holroyd.
“There are so many things that I want to do,” she said.
Besides spending time with her family, Holroyd plans to remain very active in her community. She will be volunteering at schools, getting more involved with her sorority, Chi Sigma, and the Upper Keys chapter of Business and Professional Women. She also plans to do accreditation work for police agencies across Florida.
Ramsay considers Holroyd to be a close friend and ally. Although he has talented team members to fill Holroyd’s void at headquarters, he admits, it just won’t be the same.
“She’s probably one of the most valuable people I’m going to miss and I just can’t replace. You just can’t replace a Lee Ann Holroyd,” said Ramsay. “She’s loved and beloved by the entire agency. She left a mark on the agency and community that will last a lifetime.”
As for Holroyd, although she is thrilled to embark on this well-earned next chapter, retirement is also a little bittersweet.
“I have worked with the best people, really the best people, and that is the only part that’s bittersweet for me, just missing that actual day to day, seeing them day to day,” said Holroyd. “I cannot say enough good about the people that I worked with and the agency as a whole.”
