Detectives now believe a third person involved in the plot is still on the loose.
Deputies say 50-year-old John Swanson received a blocked phone call on Sunday in which a man threatened to cut off the victim's hands and other body parts unless he paid $200,000.
On Monday, the suspect called the victim and said he would be sending someone to pick up the money on Tuesday, reports said.
The suspect allegedly told the Swanson if he comes through with the money, he would give him a break and only take $100,000. Otherwise he would take something even more valuable.
He threatened to chop off the Swanson's hands and penis, deputies said
"Not common at all. The first one that I’ve worked in 15 years," Detective Tom Zanfardino with the Collier County Sheriff's Office said. "He was terrified and traumatized."
According to deputies, the suspect called the victim again on Tuesday and told the victim to take the money to the Home Depot off Davis Boulevard in East Naples.
The victim then drove to the meeting spot, parked his car and placed the money in the rear of his car, then went inside a nearby business, reports said.
A short time later, deputies say 17-year-old John Michael Caruso of Tempe, AZ, got out of a silver car, approached the back door of the victim's car and looked inside. He then allegedly opened the back hatch of the car.
Deputies then took Caruso and the driver of the silver car, 22-year-old Tomas Possenti, a Venezuelan national, into custody.
"The instructions that we were providing were basically followed to a 'T' by the people who tried to call and pick up the money," said Zanfardino.
Possenti and Caruso were each charged with conspiracy to commit extortion.
Detectives believe the third person involved, who they are actively looking for, was the man on the phone.
They think Swanson, a businessman and developer, was specifically targeted because of a previous relationship he had with a female.
"The victim is a modes individual that would not be able to come up with that amount of money," Zanfardino said.