Ex-Felon “Dirtbags” Accused of Ordering Hit on Detainee at Florida Jail, But Questions Linger
by Jo Ellen Nott
On December 1, 2022, Florida’s Flagler County Sheriff’s Office (FCSO) arrested two ex-felons for orchestrating a beat-down in the county lockup. Sheriff Rick Staly called Margaret Watkins, 37, and her boyfriend, Raymond Dukes, 52, a pair of “dirtbags,” vowing he “won’t allow this kind of behavior in our jail.”
But that promise came too late for former detainee Jordan Simon. On June 20, 2022, a group of fellow detainees at the Sheriff Perry Hall Inmate Detention Facility allegedly carried out the hit, sending the 38-year-old to a hospital.
Sheriff Staly also said nothing about his deputies who were supposed to be guarding the jail during the assault. So it’s unclear why they didn’t peek behind the bedsheets that Simon’s attackers held up and hid behind as they stomped his already broken wrist and kicked his ribs.
In fact, there wasn’t even a firm estimate of how many blows Simon took; as reported by Flagler Live, he was struck “15 to 290 times.”
In the aftermath, five alleged attackers were charged with misdemeanor assault on a detained person: Marcus Avery Chamblin, 28; William Albert Cowles, 22; Kevonte Dequan Mikey Fobbs, 21; Timothy Alvin James, 21; and Jebea Sincere Johnson, 20.
The most recent charges were filed against Watkins and Dukes after investigators found an alleged motive for the hit: Facebook postings made by Simon’s girlfriend that incriminated the pair in a drug-dealing scheme. Watkins was freed five days after her arrest on a $25,000 bond. Dukes remains jailed, his bond set at the same amount.
He was initially arrested at home in Bunnell on May 4, 2022, when FCSO deputies seized drugs including fentanyl, methamphetamines and synthetic cathinones, also known as “bath salts.” Almost a month later, on May 3, 2022, Simon joined him at the jail after he was arrested for marijuana possession, resisting an officer, evidence tampering, domestic battery and false imprisonment. Simon was freed six days later on bonds totaling $27,000. But he was back in the jail on June 11, 2022, facing additional charges of violating his no-contact order and his conditions of release.
It was then, in a call recorded at the jail, that Watkins told Dukes about rumors that Simon had informed the police she was selling drugs. Vowing to “put respect” on her name, she allegedly instructed Dukes to offer $100 for the hit, telling him: “Gio, I need to know that I got my money’s worth on this… like I want… I… I want black eyes, like stomped in, like fuckin’ can’t walk type shit.”
It was unclear why the recording wasn’t found in time to prevent the attack on Simon. But shortly after it was made, Dukes allegedly transferred $100 to another detainee, John Harkless, to round up and pay the five detainees who carried it out.
Harkless is not charged in Simon’s assault. FCSO records show that he has been held at the jail without bond since May 26, 2022, on charges of pick-pocketing, driving on a suspended license and fleeing law enforcement.
Jail records also show that when Dukes was arrested for setting up the assault, he returned to the jail – barely two months after being released on bonds totaling $65,500. Watkins also did time at the jail in 2021 for selling drugs in a school zone, plus she was convicted of practicing nursing without a license in 2017. For the first-degree felony against them for ordering the hit, each faces up to 30 years in prison.
All of Simon’s alleged attackers remain in FCSO custody awaiting trial, except Cowles; he began a nearly 27-month sentence with the state Department of Corrections on December 29, 2022. Simon cut a plea deal and was released on his own recognizance on September 16, 2022. But he was then charged with burglary the following December 3 and returned to the jail, where he has remained ever since.
Sources: Flagler Live, Palm Coast Observer, WKMG, WNDB
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