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Florida Matriarch Sheila O'Leary Faces Second Life Sentence After Conviction in 2002 Murder-for-Hire Plot

  • Nishadil
  • September 05, 2025
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Florida Matriarch Sheila O'Leary Faces Second Life Sentence After Conviction in 2002 Murder-for-Hire Plot

In a chilling turn of events that further deepens the legal woes of Florida's Sheila O'Leary, the woman already infamous for the starvation death of her infant son, has now been convicted of first-degree murder in a two-decades-old murder-for-hire plot. The jury, after deliberating for just four hours, found O'Leary guilty of orchestrating the 2002 killing of her former lover and business partner, J.W.

"Jay" Sikes, in a wooded area of Lee County.

O'Leary, a self-proclaimed vegan matriarch, is currently serving a life sentence for the 2019 murder of her 18-month-old son, Ezra, who died of complications from malnutrition. The re-examination of Sikes' unsolved murder case in 2019, following O'Leary's initial arrest for Ezra's death, unearthed a web of deceit and alleged conspiracy that has finally culminated in this latest conviction.

During the trial, prosecutors laid out a compelling case, arguing that O'Leary had contacted Phillip Nix, a confessed hitman, offering him $5,000 to eliminate Sikes.

Nix, who testified for the prosecution, claimed O'Leary wanted Sikes dead to prevent him from divulging her involvement in an illegal marijuana grow house operation to the police. Nix further stated that he agreed to the murder, not just for the payment, but also to settle a debt owed to him by O'Leary from a previous drug deal.

The court heard how O'Leary's own brother, Douglas Street, allegedly drove Nix to the secluded location where Sikes was shot.

Street has since pleaded guilty to second-degree murder in connection with Sikes' death and is awaiting his own sentencing, a testament to the prosecution's collaborative evidence.

Taking the stand in her own defense, O'Leary vehemently denied any involvement in Sikes' murder, characterizing Nix as a liar who was solely responsible for the crime.

She attempted to paint a picture where Nix acted independently, motivated by his own drug-related debts. However, the prosecution countered this narrative, asserting that O'Leary stood to benefit significantly from Sikes' demise, not only by silencing a potential witness but also by potentially gaining access to his inheritance.

The jury's swift verdict delivers a mandatory life sentence for O'Leary, adding another layer of severe punishment to her already grim legal future.

She is scheduled for formal sentencing on August 19, a date that will solidify her fate as a woman facing two consecutive life terms for crimes spanning nearly two decades.

This case serves as a stark reminder of the long arm of justice, where past crimes, even those dormant for years, can resurface with devastating consequences for those involved.

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