The glare of the ensuing international media attention exposed Woods' secret life — and shined unprecedented attention on a tiny agency that patrols the richest town in Central Florida.
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Several current and former officers have a history of legal troubles: drug abuse, domestic violence, lying and assault, according to court and police records reviewed in six counties by the Orlando Sentinel.
Two of those officers are bodyguards whom Woods trusted with the safety of his wife, Elin Nordegren, and their two children.
And one responded to Woods' one-car accident Nov. 27.
Early that morning, two Windermere officers left their own beat to reach the crash scene first. A day later, the department later broke protocol by revealing details of what happened. International attention followed, plus the ire of law-enforcement officials for undermining the crash investigation.
Saylor defended his department's intervention, saying a life was at stake.
It was the first time in memory that Windermere police have found themselves under such scrutiny in a case so big.
"Furthermore, it should be noted that the City of Windermere, Florida has no jurisdiction in this investigation," an Orange County sheriff's advisory stated. "Information provided by the City of Windermere may, in fact, be counterproductive to the ongoing investigation into this incident."
Hiring cops who resign under investigation is an unwise risk, according to a nationally recognized expert on police liability.
"Some could be a good officer, but you're playing a long shot," said Geoffrey Alpert, chairman of the Department of Criminology and Criminal Justice at the University of South Carolina. "A short-sighted chief might do it to save money on training … but a long-sighted chief would say, ‘I wouldn't touch this guy with a 10-foot pole.' ''
Longtime Town Manager Cecilia Bernier, who hired Saylor, said she was aware of the history and records of Saylor and his officers. Though she declined to discuss specifics, Bernier expressed confidence in Saylor and his department.
"They are the best officers for this town, and I stand by the police department and the officers because they are the best department in Orange County," she said.
Mayor Gary Bruhn said he was unaware of the officers' histories but planned to discuss the matter with Bernier. The Town Council can hire and fire the manager, but members are not authorized to interfere in day-to-day business.
"Ultimately, it's the council's decision where they go with this," Bruhn said.
Saylor makes no apologies for the makeup of his department or the histories of his officers.
"I do believe cops deserve a second chance as long as FDLE [Florida Department of Law Enforcement] says they're Florida-certified," he said.