South Florida Probation Officer Acquitted of Rape Had Multiple Harassment Complaints in Past

In March 2015, Zachary Bailey, a state probation officer, was arrested after an anonymous Coral Springs woman accused him of rape. The woman, who was under Bailey's supervision after serving time on drug charges, alleged that Bailey had visited her at home, blocked the door to her bedroom, and raped her twice. The first day, she alleged he touched her vagina without consent. The second day, she filmed the pair having sex.

But in June 2016, Broward County prosecutors dropped charges, alleging that the woman had made inconsistent statements and that the video showed her instructing Bailey to have sex with her. The woman, however, has not rescinded her story — and instead sued the state Department of Corrections and Bailey last month.

Previously, news reports claimed that Bailey had an "unblemished" record in 20 years as a probation officer. But the case, which was transferred to federal court yesterday, reveals at least two complaints — from different women — where Bailey was accused of sexually harassing female offenders.

The new information raises new questions as to why prosecutors did not allow Bailey's case to continue, and whether state investigators adequately investigated complaints against him in the past. Earlier this year, Miami prosecutors became ensnared in their own Department of Corrections scandal, when they declined to charge four prison guards who oversaw the death of Darren Rainey, a black inmate with schizophrenia who was placed in a scalding hot shower for nearly two hours until he died.

A lawyer representing both Bailey and the state, Chris Whitelock, declined to comment to New Times this morning. The anonymous woman is suing the state for negligent supervision and civil rights violations, and Bailey for assault, battery, and false imprisonment, among other charges.

In one complaint from 2001, a female offender, whose name was redacted, alleged that Bailey had "made sexual advances toward her." A Bureau of State Investigations Case Summary said the woman called in to report the incident, since she "does not know what to do, she doesn't want to be violated."

The report said the case lacked physical evidence, and that the woman who'd accused Bailey of harassment was in violation of her own probation. The state did not find Bailey guilty of harassment.


But in 2015, Bailey was accused again of trying to extort offenders for sexual favors. That year, a complaint alleged that Bailey had asked to "go on a date" with the girlfriend of another one of the people he was supposed to be supervising, Donald Ray. If she didn't go through with it, the complaint alleged Bailey would accuse Ray of a probation violation:

The lawsuit doesn't make it clear how that 2015 complaint was resolved.

In the new lawsuit, the anonymous woman who accused Bailey of rape claimed that the state failed to properly investigate those claims, and, due to the state's negligence, Bailey was allowed to keep his job and allegedly assault another person.

"As early as 2001, the Bureau of State Investigations became aware that P.O. Bailey, while serving in his official capacity as a probation officer for the DOC, made sexual advances toward at least one other female probationer, who did not accept his advances and was subsequently violated thereafter," the lawsuit alleges. "The DOC failed to conduct any meaningful investigation into the allegations. If a meaningful investigation was conducted, it would have negated his future sexual predatory actions against the Plaintiff."