Suspected sexual predator caught after FDLE targets Craigslist ad

Suspect's ad stated he wanted 'kinky fun' with any race, age, body type

LIVE OAK, Fla. – An online child sexual predator investigation that began in February has led to the arrest of a man who now faces multiple criminal sex charges. 

David James Montgomery, 32, of Live Oak, is charged with four counts of transmitting harmful materials to children and one count of enticing a child online.  

According to a 16-page arrest report obtained by News4Jax, in early February, the North Florida Internet Crimes Against Children Task Force and Florida Department of Law Enforcement initiated multiple online investigations to identify sexual predators who were looking for children. 

"Before they file charges, they want to make sure they have a solid case and, here, it sounds like they do because they have a lot of evidence," said Gil Smith, News4Jax crime and safety analyst. 

Montgomery was identified as a suspect during the investigation in Columbia County. 

An undercover agent responded to a Craigslist advertisement that detectives said was posted by Montgomery. According to investigators, the advertisement said, “Hey, I’m a single guy and just got out of prison and I’m looking to have some kinky fun with any age, race, and body type.” It further went on to say, “Your # gets mine and your pic gets mine. Hope to hear from someone ASAP.”

In response to that post, the undercover agent created a fake profile and pretended to be a 14-year-old girl with a name that was redacted from the report. 

On Feb. 12, the undercover agent responded to the Craigslist ad by saying, “I might be too young.” A minute later, Montgomery replied by saying, “Send a pic and I’ll decide.”

According to a manuscript of the text messages obtained by News4Jax, Montgomery spent three days trying to persuade who he thought was a 14-year-old girl to send him nude pictures. While the agent’s messages appeared to be very coy, Montgomery’s messages were sexually explicit.

According to the messages, Montgomery explained in full detail what he wanted to do with who he thought was a teenage girl. 

At one point, Montgomery sent the undercover agent a nude photo of himself which included his face and body tattoos that were later used as evidence. Following that message, detectives said Montgomery arranged to meet the girl in the electronics department of a Lake City Walmart, but that plan was canceled because he couldn't arrange transportation to the store.

Investigators said the following day at 3:30 p.m., Montgomery sent the agent another nude pic of himself that also displayed his tattoos.

Minutes later, investigators said Montgomery sent the agent a video. According to detectives, the video showed Montgomery masturbating. After the video was sent to the agent, detectives said Montgomery began texting extremely explicit messages. 

The following day, Montgomery attempted to meet the undercover agent at a Dollar Tree store on State Road 247, but the plan was canceled because he was upset about not receiving any nude pics. 

Throughout the course of the ongoing texting conversation, Montgomery kept trying to make sure the person he was talking to was not an undercover law enforcement officer, but also kept sending explicit messages. 

"This is not considered a case of entrapment because Mr. Montgomery put an ad out, saying he's looking for sexual contact from anyone of any age and that includes a minor, so police posed as a minor and responded to the ad," Smith said.

By Feb. 15, investigators were able to positively identify David James Montgomery as a person who lives in Live Oak. 

On May 11, an FDLE agent received a subpoena from an unnamed source that was redacted in the report. The subpoena pertained to the case against Montgomery. Much of the information regarding the subpoena was redacted from the report, but Montgomery contacted that FDLE agent and agreed to an interview.

During the interview, Montgomery told the agent he was unemployed and recently moved back to Live Oak after spending four months in Kingsland, Georgia, but according to the Florida Department of Corrections, Montgomery was released from the prison on Feb. 2, which was 10 days before he was under investigation for suspected online sex crimes. 

The agent said they noticed that Montgomery had the same tattoos as the person seen nude in the photos. Montgomery later admitted to authorities that he was in the photos. 

A News4Jax criminal background check revealed that Montgomery had served two and half years in prison on drug charges.

Montgomery currently is in the Columbia County jail on a $100,000 bond. 


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