The suspect, Derek Britton, had been arrested before for allegedly stalking her weeks ago.
"He enlisted someone in the jail to beat this ex-girlfriend of his and do some further property damage at her home," said John Herrell of the Lake County Sheriff's Office.
Herrell said Britton also hired the man to break into her home, steal money and plant narcotics.
Britton was originally arrested after he allegedly stalked her and spray-painted her home earlier this month.
“It’s a pretty crazy ordeal. She’s, like, the nicest lady you will ever meet. It makes no sense,” said the victim’s son-in-law, Karlton Tillman.
As for the plot to harm the victim, deputies said a witness came forward.
"A witness came forward and let us know he was trying to offer bond money to get this guy out of jail, and then would pay him more money later on,” said Herrell.
Deputies then set up a sting at a Cracker Barrel restaurant in Leesburg.
Officials said the suspect showed up ready to pay off the person so the deed could be done.
"He had money in his pocket, ready to pay what he agreed upon," Herrell said.
Instead, deputies were waiting and arrested Britton.
“I don't know what happens when you're in your 80s, and you have a relationship and it ends. I don't know if you get bored, or what was going on in his head. Really, I have no idea," Tillman said.
Investigators said the incident is among a string of issues the victims had with the suspect.
“For about a year, he was spray-painting (her property) and we’re not sure but she had two tire stabbings, water in her gas tank twice and somebody destroyed the pool,” Tillman said.
The victim, fearing for her safety, got a restraining order.
A month later, deputies said Britton showed up at her home wearing a ski mask and was in possession of a box cutter and spray paint.
“Spray painting her bedroom window and trying to dismantle or vandalize her security camera,” Herrel said.
Deputies said he even brought a stool in order to reach her security cameras, but she caught him in the act.
"He struck her and they began rolling around on the ground," said Herrell.
Both were injured during the fight, but will be all right, authorities said.