BREAKING: Turmoil Continues at City Hall as Key West Ousts Building Chief, Code Enforcement Staff
City ends chief building official’s probation, brings in outside firm as shakeup widens at 1300 White Street.
Turmoil continues around the building, planning and code enforcement departments at City Hall, with the latest shakeup marked by the firing of the city’s chief building official and the departure of at least two members of the code enforcement division, according to city officials.
In an email sent Wednesday morning to the mayor, city commissioners and senior staff, Assistant City Manager Rod Delostrinos said the probationary period for Chief Building Official Troy Winterfield was not extended and has concluded.
“We thank Mr. Winterfield for his work and wish him the best as he transitions to other opportunities,” Delostrinos wrote.
In a text exchange with one commissioner, Winterfield said this about the firing:
“Thank you Commissioner the manager was not to happy when I closed your permits and hed he didn’t like how I assisted Commissioner Haskell with the complaint about the gas and oil smell at the marina”
Delestrinos wrote to commissioners that in order to ensure continuity of services, the City has retained All Aspects to assist with Building Department operations, including chief building official duties. Delostrinos said residents and contractors should not experience delays in permitting or related services.
The city is coordinating with Human Resources to recruit and select a full-time chief building official, Delostrinos said.
Winterfield was hired to replace felony-indicted former CBO Raj Ramsingh, a key member of the Bubba Bozo Trio.
Before moving to Key West in 2022, Winterfield served as building official in Anoka, according to prior city materials. Winterfield has more than 45 years of experience in the building trades, including 16 years as a building official and zoning administrator. In previous public statements following his hiring, Winterfield said he was honored to serve as Key West’s chief building official and took pride in helping the island grow in ways that are safe, sustainable and consistent with its character.
The departures come amid heightened scrutiny of permitting and enforcement practices at City Hall, where regulatory departments have faced repeated leadership turnover in recent years. City officials did not provide details Wednesday regarding the circumstances surrounding the departures of code enforcement staff.
The email announcing Winterfield’s departure was copied to City Manager Brian Barroso and department directors and managers. No timeline was provided for hiring a permanent replacement.
This is an evolving story. Watch this space.


