TALLAHASSEE, Fla. — Former Republican congressional candidate Jackie Toledo is suing her ex-campaign manager, Fred Piccolo, over sexually explicit pictures he sent her during the campaign — allegations Piccolo says are tied to a dispute over her failure to pay him for work during the campaign.
Toledo, who left a Tampa-area Florida House seat to run for Congress, filed the lawsuit Monday night in Hillsborough County court. It alleges he sent her unwanted sexually explicit photos and text messages offering “advice for breast augmentation,” using his own wife’s breasts as a reference.
At the time he allegedly sent the photos and texts in May, Piccolo was working as Toledo’s campaign manager. The lawsuit includes more than 20 pages of text messages between Piccolo and Toledo, who lost her Republican congressional primary to former Florida Secretary of State Laurel Lee. Many of those pictures include Piccolo in pictures in his underwear and openly suggestive messages. Piccolo did not dispute the authenticity of the photos or texts.
Piccolo, who previously served as communication director to Gov. Ron DeSantis, says Toledo released the photos and filed the lawsuit because of a dispute over a disagreement about non-payment for his work on the campaign.
“I have known Jackie Toledo for 10 years, I thought we were friends. At no point did the banter we engage in exceed those boundaries,” he said Monday night. “Jackie got wind of intent to file a lawsuit for failure to pay and this is an outrageous attempt to sully my name to prevent that lawsuit.”
Toledo, who did not respond to requests seeking comment, in the lawsuit alleges that Piccolo sent the pictures to intentionally get fired in order to collect a $100,000 payout he would have received if his employment was terminated.
Anthony Pedicini, who served as Toledo’s top consultant and whose GOP consulting firm Piccolo has worked for, said he does not agree with the allegations outlined in the lawsuit.
“I know Fred never quit the campaign or tried to get fired,” he said. “This is out of left field. This would be the October surprise of my century.”
Piccolo allegedly sent Toledo the photos via text throughout the summer as Toledo was running in a crowded Republican primary in Tampa-area congressional seat newly drawn as part of the state’s redistricting cycle. Many of the text messages include both images of what appear to be Piccolo in boxer shorts and explicit messages, some of which are tied to campaign operations.
On May 23, Piccolo texted a picture of him shirtless with the message “Monday motivation. For every $10k you get to pick any photo.”
The photo was among several included in the lawsuit, most of which portrayed Piccolo in his underwear in what appeared to be a bathroom mirror. In most instances, Toledo did not directly respond to the pictures.
In one July 2022 text, Piccolo sent a smiley face and shirtless picture saying “pre gym.”
In response, Toledo said “you are productive already,” and immediately sent a second message asking if he had seen the “LL ad,” a reference to a new TV ad put out by the Lee campaign.
In mid-August, copies of text messages included in the lawsuit between Toledo and Piccolo apparently show their relationship deteriorating. In one text message, Piccolo expressed anger over Toledo reaching out to DeSantis’ office about the governor asking him to work as a communications adviser to Hillsborough County State Attorney Susan "Suzy" Lopez. DeSantis had picked Lopez that month to replace Democrat Andrew Warren, the elected prosecutor who the governor suspended, in part, for signing pledges indicating he would not prosecute people for violating state laws prohibiting gender-affirming care or those who violated the state’s newly-implemented 15-week abortion ban. Warren is currently challenging his suspension in court.
“So the governor has asked me to help direct the communications efforts of the state attorney's office here in Hillsboro [sic] after he fired Andrew Warren,” Piccolo texted on Aug. 5. “Doesn’t mean I’m leaving the campaign I can still do work for both. I'm working as a consultant for the governor's project.”
“But when the governor calls you don’t say no especially when I worked for him before,” he added.
Toledo expressed shock by the text.
“I don’t even know what to say because I am 17 days out,” she responded. “And I can’t think of anything but.”
Less than a week later, on Aug. 11, Piccolo texted Toledo, apparently in anger, after she had reacted out to DeSantis’ office to ask about his contractual relationship with Warren.
“You called the governor’s office,” he said. “That is stepping over the line.”
“I want to know if there is a conflict of interest?” Toledo responded. “You have an active contract with me.”
DeSantis communications director Taryn Fenske says she is the one who recommended Piccolo for the position in the Hillsborough County State Attorney’s office.
“I was asked if I knew anyone in communications who could do it,” she said Monday night. “I made the connection and recommendation.”
