Florida duo arrested after planned sexual encounter turns deadly with botched car robbery, deputies say

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A man and woman were arrested in connection to a dead man who was found on the side of the road last June, according to the Marion County Sheriff's Office. 

Jessica Long, 37, and Michael Montgomery, 47, were charged with murder while engaged in a robbery after the incident that unfolded in Marion County on June 27, 2023. 

Last summer, deputies responded to the 7600 block of NW 77th Terrace near West Highway 326 after a caller reported a dead body on the side of the road. The man was later identified as Wayne Barlow, who was 40 years old at the time of his "suspicious" death, deputies said. 

The Medical Examiner's Office determined that the cause of death was a gunshot wound to the head, and they also found evidence of strangulation and blunt force trauma. The official manner of death was ruled as a homicide. 

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His death was a result of Long and Montgomery's alleged conspiracy to steal his car, according to deputies. Text messages between Long and Barlow revealed that the two planned to meet up in the woods to have sex, which he would pay her for, according to the arrest affidavit from the Marion County Sheriff's Office.  

When Barlow sent Long $80 via Cash App, Long gave Montgomery a "signal" that meant "it was time to go ahead with the plan," the affidavit added. The alleged plan called for Montgomery – "the muscle" – to steal Barlow's car while he was having sex with Long in a secluded area they found in the Regal Park area of Ocala. 

Photo: Marion County Sheriff's Office

"Montgomery advised that things did not go according to plan," the affidavit said. 

Once Barlow realized they were trying to steal his car, he reportedly attacked Long. That's when Montgomery allegedly used a bike lock to subdue him in the car and roughed him up before Long drove them to another secluded area, where his body was eventually found. 

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There, a full-blown fight broke out between the parties, the affidavit said. Montgomery pulled him out of the car and assaulted him with a "pipe-like object" before trying to run him over, deputies said. When that didn't work, Montgomery approached him and shot him, according to the Marion County Sheriff's Office. 

"Make sure he's dead," Long said, according to the arrest affidavit. 

"Montgomery advised he took part in the attack on the victim for a couple reasons and those reasons were for free drugs and for sex he didn't have to pay for," the affidavit said. 

Photo: Marion County Sheriff's Office

They then hatched a plan to go to Family Dollar to buy supplies, including bleach, to clean up the blood, the affidavit said. 

Deputies also found trash in a dumpster behind the Aquatic Center in Ocala that contained a towel with suspected blood on it, paperwork with Barlow's name on it and a black C02 BB Gun pistol – a replica of a real handgun – with a grip missing. That grip was found near Barlow's body. 

Long and Montgomery then fled the area, according to deputies. 

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During the investigation, deputies went back to the area where Barlow's body was found. There, they found a black and silver Phoenix Arms .22 caliber handgun about 30 feet from where his body was found. 

Long and Montgomery are both being held at the Marion County Jail without bond. Montgomery is facing additional charges including parole violation, resisting arrest and aggravated battery. 

Long has a lengthy criminal history in Marion County, including previous arrests for grand theft, resisting arrest, prostitution and drug possession, arrest records show.