Fred Piccolo Jr., the director of marketing and media for New College of Florida and a longtime state political powerbroker, was arrested Tuesday by the Manatee County Sheriff’s office and charged with exposure of sexual organs and is being held in jail.

It was his second subsequent offense, according to the charge.

According to an arrest warrant obtained by Suncoast Searchlight/Florida Trident, Piccolo allegedly stopped his vehicle while wearing nothing but a T-shirt and exposed himself to a Manatee County woman after asking her for directions. 

The victim told deputies the suspect claimed he needed directions as he did “not have his phone because he just found out his girlfriend was married — her husband came home ‘in the middle’ and he ran out with just a shirt.” 

The woman said once she noticed the man was holding his erect penis in his hand, she took off running and called 911. She took down the car’s license plate and later identified the suspect as Piccolo from a photo lineup. 

The alleged incident happened on March 28.

Eric Reisinger, an attorney representing Piccolo, wrote in an email to Suncoast Searchlight/Florida Trident that Piccolo takes medication for Parkinson’s disease that he said has caused “compulsive behavior and hypersexuality as side effects,” which “are causing Mr. Piccolo to behave in a manner inconsistent with his established character.”

This was not the first time that Piccolo, who has held a series of high-profile public relations roles in Gov. Ron DeSantis’s offices and for former Florida House Speaker and current New College President Richard Corcoran, has been charged with exposure – or accused of sexual harassment. 

According to three separate probable cause affidavits filed between August and September 2024, Piccolo has been charged with a series of indecent exposure incidents at retail stores in the University Town Center Mall. 

In the first incident, detailed in an affidavit dated Aug. 22, Piccolo allegedly exposed his erect penis to a female assistant manager inside the fitting room of Banana Republic while masturbating. Surveillance footage corroborated the woman’s account. She walked away; Piccolo dressed and fled the store without buying anything. 

A second incident occurred on Sept. 3 at Dillard’s. Witnesses, including two female employees, reported Piccolo was entirely naked inside a fitting room, his genitals in full view. One associate described him as “totally naked with no clothes on,” prompting another to abandon her attempt to help him. 

And just one day later, on Sept. 4, another complaint was filed after Piccolo allegedly repeated the behavior at the same Dillard’s store, exposing himself to a woman assisting him with clothing. The encounter, again supported by security footage, led deputies to file a separate affidavit for criminal exposure of a sexual organ. 

All three cases are set for trial next month in Sarasota County. 

New College did not respond to several emails seeking comment and questioning whether the school had vetted Piccolo before hiring him or knew about his prior offenses.  

New College’s staff page for Piccolo was no longer active as of Wednesday. 

A high-powered political operative 

Piccolo has wielded significant influence in Florida political circles, deploying to manage high-stakes communications for DeSantis and his allies. 

Piccolo served as spokesperson for the Florida Speaker of the House when Corcoran held the role from 2016 to 2018, and remained in that position under Republican state Rep. Jose Oliva. In July 2020, DeSantis hired Piccolo to run his communications operation, and in 2021, Piccolo started a new position working for the Florida Department of Education’s Division of Colleges. 

After DeSantis removed elected Hillsborough County State Attorney Andrew Warren in August 2022 following his refusal to enforce bans on abortion and transgender healthcare, the governor tapped Piccolo to handle public relations for his replacement, Susan Lopez. 

In his role with Lopez’s office, Piccolo coordinated a communications strategy to introduce Lopez and manage her opposition.  

In an email obtained by the Florida Trident, Piccolo proposed a variety of tactics to respond to a protest lodged by Democratic politician Nikki Fried over Warren’s ouster. 

They ranged from doing nothing to directly attacking the protest with a “smack” accusing Fried of “politiSAical [sic] theater.” 

But filings in both civil and criminal court paint a picture of a man accused of leveraging positions of trust for inappropriate and unlawful behavior. 

A campaign derailed by infighting, allegations of harassment

In a lawsuit filed in October 2022 in Hillsborough County Circuit Court, former state Rep. Jackie Toledo accused Piccolo of intentional infliction of emotional distress and outrageous conduct during the 2022 election season.

Hired as Toledo’s campaign manager, Piccolo allegedly sent her a barrage of unsolicited, sexually explicit messages — many of which intertwined campaign responsibilities with overt harassment. 

Screenshots attached to the complaint show a string of such texts.

In one message, Piccolo sent a shirtless photo and wrote, “For every $10k u raise today you can pick any photo.” In another, he appeared nearly nude and described the image as “Monday Motivation.” Other messages referenced his wife’s breast augmentation and offered unsolicited “advice” to Toledo on her own appearance. 

“Oops,” wrote Piccolo in a text message following a lascivious photo, according to a screenshot attached to the lawsuit. “That was a Parkinson’s send.” 

Toledo’s complaint alleges the harassment was calculated — an effort by Piccolo to provoke his own firing and trigger a $100,000 payout under a clause in his campaign contract. Toledo’s legal filing describes Piccolo’s behavior as “shocking, atrocious, and utterly intolerable in a civilized community.” 

The complaint was voluntarily dismissed in April 2023 and included a confidential settlement.

“What’s happened is heartbreaking but, sadly, not surprising,” Toledo said in a statement to Suncoast Searchlight/Florida Trident. “I came forward years ago and filed a lawsuit to stop Fred Piccolo’s behavior before it could harm others. I hoped it would spark accountability. Instead, he ignored the consequences, and now more victims have come forward.”

Toledo said she stands with those impacted by Piccolo’s alleged behavior. 

“I know how devastating and isolating this experience can be,” she said in the statement. “I hope law enforcement now takes the steps they should have taken long ago.”

This story was jointly produced by  Suncoast Searchlight and The Florida Trident. Suncoast Searchlight is a nonprofit newsroom of the Community News Collaborative serving Sarasota, Manatee, and DeSoto counties. Learn more at suncoastsearchlight.org. The Florida Trident is a local investigative news outlet focusing on government accountability and transparency across Florida. Learn more at floridatrident.org.