- December 19, 2025
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The Winter Park Police Department is in for a major overhaul in leadership.
Winter Park will say goodbye to its four highest-ranking officers over the next 18 months, with Chief Brett Railey, Deputy Chief Art King and captains Vern Taylor and Jess Johnson planning to retire.
King will be the soonest to retire, leaving the police department by March and ending a career of more than 30 years in the city of culture and heritage.
City Manager Randy Knight said the police department will surely adapt. Multiple officers have been moving up the ranks, including three promoted to lieutenant in the past two years, he said.
“They do such a good job of training and they’ve known this was happening for years now,” Knight said. “There’s been a push to make sure everyone has been well trained and promoted.”
“There’s no doubt there’s a brain drain when you lose that many top level people … but I’m confident they’re on top of it.”
But the retirements come in the wake of violent crime trends within the city. Winter Park saw three armed robberies in a span of only 10 days last September, including one just off of Park Avenue.
Last September through December saw a growing number of burglaries as well, with a total of 44 residential burglaries hitting Winter Park at an average rate of 11 burglaries a month, according to the online crime map on the Winter Park Police website. Winter Park saw 38 burglaries in that four month span the previous year.
Mayor Ken Bradley also said he felt confident the police department would find the right officers to replace their leadership.
“There will obviously be a very orderly transition,” Bradley said. “How do you avoid this in the future? I have no earthly idea, it just speaks to how the [deferred retirement option plan] works and how our pensions work.”
The deferred retirement option plan allows officers to collect an alternative retirement payment that builds up throughout their final years of service with the help of accrued interest. That payment would not go into their regular retirement pension. At retirement that payment could pay out in a lump sum, rather than over many years. In theory, the plan was created to encourage the retirement of higher-paid, senior employees to a make room for advances among younger employees.
Bradley added that a proper send off for the retiring officers is in order.
“When this day comes, we’ll have to appropriately recognize those who have served our city so faithfully and so well,” Bradley said. “It is, in some respects, the end of an era.”
Chief Railey began his law enforcement career in 1977, working for the Florida Highway Patrol as a dispatcher and Rollins College as a campus police officer before joining the Winter Park Police Department as a patrol officer in 1981. He was appointed Winter Park Chief of Police in 2009 and is expected to retire in 17 months, Knight said.
Cpt. Vern Taylor, who will see his 26-year career come to an end in 16 months, had nothing but praise for Winter Park and their police department.
“I had a great time,” Taylor said. “I’m very blessed to be in Winter Park.”
Taylor said their continued quality of service will help the police department transition. Winter Park officers often go beyond their jurisdictional reach, he said, whether it’s responding to crime in Orange County or a call about a Florida gator on the loose in a resident’s backyard.
“If you call, we’ll respond,” Taylor said.