Filing # 159860192 E-Filed 10/24/2022 04:38:25 PM

IN THE CIRCUIT COURT OF THE THIRTEENTH JUDICIAL CIRCUIT

IN AND FOR HILLSBOROUGH COUNTY, FLORIDA
CIVIL DIVISION

JACKIE TOLEDO,

Plaintiff, Case No.:

v. Division:

FREDRICK J. PICCOLO JR.,

Defendant.
___________________________________/

COMPLAINT FOR OUTRAGE, INTENTIONAL INFLICTION OF EMOTIONAL

DISTRESSS AND DEMAND FOR JURY TRIAL

Plaintiff, JACKIE TOLEDO, by and through undersigned counsel, hereby sues Defendant,

FREDRICK J. PICCOLO JR., and alleges:

JURISDICTION AND VENUE

1. This is an action for damages which exceed $30,000.00,1 exclusive of attorneys’

fees, interest, and costs.

2. At all times material, JACKIE TOLEDO (“Ms. Toledo”), was a resident of

Hillsborough County, Florida.

3. At all times material, FREDRICK PICCOLO (“Mr. Piccolo”), was a resident of

Leon County, Florida, however he was conducting, engaging in, or carrying on a business in

Hillsborough County, Florida under the trade name PICCOLO STRATEGIC

COMMUNICATIONS.

1
The Civil Cover Sheet required to be filed with this Complaint seeks at question No. 2, “the estimated amount of the
claim, rounded to the nearest dollar”; Plaintiff has inserted $30,001 in order to comply with jurisdictional minimums,
but with the understanding the actual value of this case is increasing daily, and is therefore, not subject to a precise
assessment or estimate as of the date of filing this Complaint.

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 4. Venue for this action is proper in Hillsborough County, Florida, because the

relevant transactions and material events giving rise to this action occurred in Hillsborough

County, Florida.

FACTS COMMON TO ALL CLAIMS

5. On March 7, 2022, Ms. Toledo announced her decision to run as a Republican

candidate for election to the United States House of Representatives to represent Florida’s 15th

Congressional District.

6. For assistance with her electoral campaign, on May 2, 2022, Ms. Toledo’s

Campaign, JACKIE TOLEDO FOR CONGRESS (“Toledo Campaign”), entered into an

agreement with Mr. Piccolo, doing business under the trade name PICCOLO STRATEGIC

COMMUNICATIONS, to hire Mr. Piccolo as her campaign manager.

7. Mr. Piccolo’s agreement provided a monthly salary, reimbursement of expenses,

and various bonuses linked to certain contingencies. Two bonuses were contingent on a primary

election win or general election win. One of the bonuses, contingent on a loss in the primary

election, provided for a $25,000 payment to Mr. Piccolo.

8. The Agreement also provided that if either party terminated the arrangement, Mr.

Piccolo would be entitled to receive a $100,000 payment (“Termination Penalty”).

9. As Ms. Toledo’s campaign manager, Mr. Piccolo maintained a position of trust,

akin to a fiduciary, obligating Mr. Piccolo to act in accordance with this significant position of

trust.

10. On or about May 18, 2022, while Mr. Piccolo was already operating as Ms.

Toledo’s campaign manager, Mr. Piccolo sent Ms. Toledo unwanted, unsolicited, inappropriate,

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 and grossly offensive sexually harassing text messages and images. See Exhibit A, Text Messages

between Mr. Piccolo and Ms. Toledo.

11. While some of Mr. Piccolo’s text messages offered advice for breast augmentation

and referenced Mr. Piccolo’s wife’s breasts, others included images of a sexual and inappropriate

nature. Ex. A, p.1-2. At least one image involved Mr. Piccolo taking a photo of his erection, while

others involved Mr. Piccolo in various states of undress, generally only wearing undergarments.

Ex. A, p.1, 3-8, 14.

12. These text messages and images were not only inappropriate, but particularly

offensive when they were, at times, sent in response to campaign-related questions Ms. Toledo

posed to Mr. Piccolo. Ex. A, p.3.

13. Mr. Piccolo’s offensive text messages were also sent with references to the

campaign that Mr. Piccolo was contracted to manage. On at least one occasion, Mr. Piccolo sent

Ms. Toledo a shirtless image with his hand in his underwear, stating it was sent as “Monday

Motivation.” Ex. A, p.4. In the same message, Mr. Piccolo stated, “For every $10k u raise today

you can pick any photo.” Ex. A, p.4.

14. Mr. Piccolo was aware of the important role he played in Ms. Toledo’s electoral

campaign and the position of trust he maintained to the Toledo Campaign and Ms. Toledo; despite

this, Mr. Piccolo continued to send these patently inappropriate, harassing, and offensive sexual

text messages and images into July 2022, as Ms. Toledo’s campaign intensified. Ex. A, p.14.

15. As an experienced consultant, Mr. Piccolo was aware of the significant personal

stress and pressure electoral candidates experience as an election intensifies and the election date

approaches. Despite this knowledge and being personally aware of the stress Ms. Toledo was

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 experiencing because of his unique position of trust and proximity to Ms. Toledo, Mr. Piccolo took

advantage of the timing and Ms. Toledo’s vulnerability to undertake his highly offensive conduct.

16. Mr. Piccolo sent grossly inappropriate messages and images to cause Ms. Toledo

distress and emotional harm, in hopes she or the Toledo Campaign would terminate the

Agreement, entitling Mr. Piccolo to collect no less than $100,000 pursuant to the Termination

Penalty.

17. On August 5, 2022, less than three weeks before the primary election closed, Mr.

Piccolo advised Ms. Toledo that he would be working as a communications consultant to assist

with the controversy related to the removal and replacement of Hillsborough County State

Attorney Andrew Warren with Suzy Lopez. Ex. A, p.21.

18. After accepting the consultant role related to the Hillsborough County State

Attorney controversy, Mr. Piccolo failed to maintain his obligations to the Toledo Campaign,

further attempting to force-through a termination of the Agreement.

19. After Ms. Toledo reached out to the Governor’s office to determine if Mr. Piccolo’s

engagement with the Governor was a conflict of interest with her campaign, Mr. Piccolo

reprimanded Ms. Toledo for intruding into his affairs. Ex. A, p.17. In this reprimand, with less

than two weeks before the primary election closed, Mr. Piccolo invited Ms. Toledo to fire him.

Ex. A, p. 17.

20. Ms. Toledo was caused emotional distress and economic injuries by Mr. Piccolo’s

continuous, offensive, and sexually harassing conduct amidst a high-stress and high-profile

electoral campaign.

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 COUNT I – OUTRAGE

Plaintiff, Ms. Toledo, realleges and reaffirms paragraphs 1-20, as if same were fully set

forth herein.

21. Mr. Piccolo intentionally sent highly offensive, sexual images and messages to the

Ms. Toledo whose campaign he was contracted to manage, while intertwining these offensive

messages with campaign affairs, with the intention to offend and harass Ms. Toledo. These

offensive acts were intended to force Ms. Toledo or the Toledo Campaign to terminate the

Agreement and entitle Mr. Piccolo to receive a $100,000 payment.

22. Mr. Piccolo’s conduct was extreme and outrageous; that is, under the

circumstances, it goes beyond all possible bounds of decency and is regarded as shocking,

atrocious, and utterly intolerable in a civilized community.

23. The conduct described above directly and proximately caused Ms. Toledo’s injuries

in that it directly, and in a natural and continuous sequence produced or contributed substantially

to causing Ms. Toledo’s injuries.

24. As a direct and proximate result of Mr. Piccolo’s outrageous intentional conduct,

while in a position of trust akin to a fiduciary, Ms. Toledo has suffered severe and ongoing

emotional distress, humiliation, lasting psychological damage, mental anguish, loss of capacity for

enjoyment of life, and aggravation of previously existing conditions. These losses are either

permanent or continuing, and Ms. Toledo will continue to suffer losses in the future

25. Mr. Piccolo had actual knowledge of the wrongfulness of his conduct and the high

probability that injury or damage to Ms. Toledo would result and, despite that knowledge, he

intentionally pursued his outrageous course of conduct, resulting in injury or damage to Ms.

Toledo. In accordance with § 768.72, Fla. Stat. (2022) and the Florida Rules of Civil Procedure,

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 Ms. Toledo will seek to amend her complaint to assert a claim for punitive damages for Mr.

Piccolo’s intentional misconduct or gross negligence.

WHEREFORE, Plaintiff, JACKIE TOLEDO, respectfully requests this Honorable Court,

enter judgment for damages in excess of $30,000.00 against Defendant, FREDRICK J. PICCOLO

JR., including taxable costs and such other and further relief as the Court may deem appropriate.

Plaintiff respectfully requests a trial by jury on all issues so triable.

COUNT II – INTENTIONAL INFLICTION OF EMOTIONAL DISTRESS

Plaintiff, Ms. Toledo, realleges and reaffirms paragraphs 1-20, as if same were fully set

forth herein.

26. Mr. Piccolo’s conduct of sending offensive, sexual images to Ms. Toledo, while

intertwining these offensive messages with campaign affairs was intentional or reckless and Mr.

Piccolo knew or should have known that emotional distress would likely result. These offensive

acts were intended to force Ms. Toledo or the Toledo Campaign to terminate the Agreement and

entitle Mr. Piccolo to receive a $100,000 payment.

27. Mr. Piccolo’s conduct was extreme and outrageous; that is, under the

circumstances, it goes beyond all possible bounds of decency and is regarded as shocking,

atrocious, and utterly intolerable in a civilized community.

28. The conduct described above directly and proximately caused Ms. Toledo’s injuries

in that it directly, and in a natural and continuous sequence produced or contributed substantially

to causing Ms. Toledo’s injuries.

29. As a direct and proximate result of the foregoing, Ms. Toledo has suffered severe

and ongoing emotional distress, humiliation, lasting psychological damage, mental anguish, loss

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 of capacity for enjoyment of life, and aggravation of previously existing conditions. These losses

are either permanent or continuing, and Ms. Toledo will continue to suffer losses in the future.

30. Mr. Piccolo had actual knowledge of the wrongfulness of his conduct and the high

probability that injury or damage to Ms. Toledo would result and, despite that knowledge, he

intentionally pursued his outrageous course of conduct, resulting in injury or damage to Ms.

Toledo. In accordance with § 768.72, Fla. Stat. (2022) and the Florida Rules of Civil Procedure,

Ms. Toledo will seek to amend her complaint to assert a claim for punitive damages for Mr.

Piccolo’s intentional misconduct or gross negligence.

31. WHEREFORE, Plaintiff, JACKIE TOLEDO, respectfully requests this Honorable

Court, enter judgment for damages in excess of $30,000.00 against Defendant, FREDRICK J.

PICCOLO JR., including taxable costs and such other and further relief as the Court may deem

appropriate. Plaintiff respectfully requests a trial by jury on all issues so triable.

Respectfully submitted on October 24th, 2022, by:

/s/ Dale Swope

DALE M. SWOPE
FL Bar No.: 261270
SWOPE, RODANTE P.A.
1234 East Fifth Avenue
Tampa, FL 33605
Tel: (813) 273-0017
[email protected]
[email protected]

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