Inside a DeSantis appointee's taxpayer-funded spending spree
Records show former Orange County Supervisor of Elections Glen Gilzean spent hundreds of thousands of dollars on self-promotion and payments to allies of Ron DeSantis and other Republican leaders.
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The political appointee picked by Florida Gov. Ron DeSantis to run elections in Orlando last year spent hundreds of thousands of dollars of taxpayer money on campaign-style self-promotion, contracts with personal friends, and payments to allies of the Republican governor and other GOP leaders in Tallahassee.
During a 10-month stint as the interim Supervisor of Elections in Orange County, records show DeSantis appointee Glen Gilzean steered work to an assortment of businesses and organizations run by Republican operatives — ranging from the governor’s former communications director to state Rep. Susan Plasencia (R-Orlando).
Gilzean also awarded a lucrative legal contract to a law firm run by the best man at his wedding — and a marketing contract to a newly created video production company that corporate, obituary, and email records suggest involved his best man’s brother.
And Gilzean spent as much as $750 an hour on lawyers — plus more than $100,000 on a series of often self-aggrandizing videos for social media, including one spot, internally dubbed “Glen’s Story,” that featured people praising and celebrating Gilzean for becoming Orange County’s first African American supervisor of elections.
DeSantis appointed Gilzean as Orange County’s top elections official in March 2024, after the county’s longtime, independently elected elections supervisor abruptly retired just ahead of the 2024 presidential election with less than a year remaining in his final term. Gilzean, a Republican appointee who was unlikely to win re-election in Democratic-heavy Orange County, opted not to run for a full term and left office in January.
DeSantis moved Gilzean over from the Central Florida Tourism Oversight District, where Gilzean had been given a $400,000-a-year job running the city-like government at Walt Disney World that was once controlled by Disney but is now run by a board of the governor’s political appointees.
Gilzean’s time atop the agency formerly known as the Reedy Creek Improvement District was marred by a series of controversies stemming from no-bid contracts for politically plugged-in vendors, jobs for GOP allies, and a mass exodus of veteran staff — some of whom accused Gilzean and the DeSantis-appointed board of incompetence and intentional dysfunction.
Gilzean’s brief tenure as the top elections official in Orange County ultimately erupted in similar scandal after county auditors discovered that Gilzean had signed off on millions of dollars in unauthorized spending and overspent his taxpayer-funded budget.
Gilzean denied wrongdoing and accused critics of engaging in a “witch hunt.” But his office admitted in court that it had fallen nearly $800,000 into the red during Gilzean’s final month in office and was unable to make office payroll.
Much of the public controversy at the time focused on several large grants Gilzean awarded shortly before leaving office — including a $2.1 million gift to a local college to fund scholarships in Gilzean’s name.
But at least one of those large grants was also used to steer work to a preferred vendor. Records and interviews show that Gilzean’s office pushed a grantee to use a portion of the money it received from the elections office to buy products from a company run by a prominent DeSantis supporter — the same vendor to whom Gilzean had once given a no-bid contract while running the tourism district at Disney.
Gilzean hung up when reached by phone. He would not answer specific questions sent to him by email.
But Gilzean texted a short statement in which he attacked Democratic policies, accused the Democratic Party of alienating communities of color, and condemned Orange County Mayor Jerry Demings and newly elected Orange County Supervisor of Elections Karen Castor Dentel. The two Democratic politicians have criticized Gilzean’s handling of taxpayer money.
“My commitment to my community is unwavering,” Gilzean wrote in the text message. “Everything we did was rooted in increasing voter education and turnout.”
Castor Dentel — who took office in early January after winning just over 40 percent of the vote in a four-way race — has been trying to claw back some of Gilzean’s spending. She announced earlier this month that several groups that received large grants from Gilzean had agreed to return more than $3 million to the elections office.
But not everyone wants to give cash back to Orange County taxpayers.
What follows is a closer look at some of Gilzean’s spending — including who he spent money on, how he did so, and what he bought.
Friends and family
Glen Gilzean, a former president of the Central Florida Urban League, and Michael Sasso, an Orlando-area attorney who was the best man at Gilzean’s wedding, have a history of helping each other.
In early 2023, for instance, records show that Sasso listed Gilzean as a personal reference on an application Sasso submitted to Gov. Ron DeSantis for an appointment to the Central Florida Tourism Oversight District.
Sasso, a DeSantis donor whose wife was later appointed by the governor to the Florida Supreme Court, got the job. He became one of DeSantis’ inaugural picks for the board of the district formerly known as Reedy Creek after DeSantis and the Florida Legislature control stripped control of the agency away from Disney. The move came in retaliation for Disney’s decisions to publicly criticize anti-LGBTQ+ legislation that DeSantis had signed into law and to cut the governor and lawmakers off from company campaign contributions.
After Sasso was appointed to the new Disney board, Gilzean used Sasso as a reference when Gilzean applied to become the tourism district’s new $400,000-a-year administrator. Sasso and the other board appointees then voted to give the job to Gilzean.
Sasso later stepped down from the tourism board. But he and Gilzean began working together again after DeSantis put Gilzean in charge of the Orange County Supervisor of Elections office — and its roughly $20 million annual budget.
About three months after he became supervisor, Gilzean awarded a no-bid contract paying up to $450-an-hour to Sasso & Sasso, a law firm that Michael Sasso runs with his father.
Records show the SOE office ultimately paid Sasso & Sasso more than $130,000, primarily to work on litigation the office faced during the 2024 elections.
Sasso did not respond to requests for comment.
Sasso wasn’t the only high-priced lawyer drawing checks from Gilzean’s elections office.
Records show that, under Gilzean, lawyers at Gunster, the large Florida law firm led by former Republican U.S. Sen. George LeMieux, billed the Supervisor of Elections nearly $750 an hour for various work. Attorneys from the Tallahassee and Miami offices of Jones Walker billed the office up to $375 an hour. And lawyers at the local firm Fishback Dominick billed up to $350 an hour.
Sasso & Sasso may not have been the only Sasso family business cashing checks from Gilzean’s office, either.
In September, records show that Gilzean’s office awarded a contract for video production, graphic design, and other media services to a company identified in the contract as “StarProductions LLC.” It was, according to emails, the only vendor to respond to an invitation to negotiate for “strategic communications services” that the Supervisor of Elections office had posted online.
There is no company by that name in Florida, according to state corporate records. But about two weeks after Gilzean’s office approved the award, records show a company called “Star Production Group LLC” was incorporated in Florida. That’s the company name that appears on all the subsequent invoices submitted to the SOE.
State corporate records identify a person named Amanda Dasher as the manager of Star Production Group. She is the only name that appears on any of the company’s public corporate filings.
But records show someone named Amanda Dasher has been a partner in at least two other businesses — Pigeon Media LLC and Cabin 7 LLC — with a person named Ian Sasso. Michael Sasso has a brother named Ian who has a significant other named Amanda, according to a recent obituary. And Ian Sasso has a company called Sasso Media Group that operates out of the Sasso & Sasso law office.
What’s more, emails between various staffers in the Orange County elections office and a Gmail address used by Star Production Group repeatedly refer to someone named “Ian.”
For instance, in October, the Star Production Gmail account sent a question about scheduling to Jodie Bell, who was, at the time, the SOE’s associate director of community outreach.
“Ian mentioned there was discussion of a possible, second in-office shoot this coming Saturday,” a person who identified themselves as “Amanda” wrote in the email. “Is this something confirmed that we should start planning for, or no?”
“I’ll keep you and Ian posted on that,” Bell responded.
And in early December, when the Star Production Gmail account submitted several invoices to the elections office, the email was signed by someone named “Ian.”
Neither Amanda Dasher nor Ian Sasso could be reached for comment. No one responded to emails sent to the Star Production Gmail account or answered calls or texts to the phone number the company provided to the Supervisor of Elections office. Michael Sasso did not respond to questions about his brother, either.
Records show Gilzean’s office ultimately paid more than $42,000 to Star Production Group — through a series of payments that were all made in December, just before Gilzean left office.
The company primarily produced a series of campaign-style, mini-documentaries about the Supervisors of Elections office that typically featured Gilzean boasting about his accomplishments and others praising him. Gilzean and SOE staff posted many of the videos on the office’s Instagram account.
Some of those glowing testimonials came from people representing organizations that also received funding from Gilzean’s office.
“Partnering with Supervisor Glen Gilzean is honestly being a part of history here in Orange County,” a board director for the Orlando Regional Realtors Association said in one of the videos.
Gilzean had just given a $45,000 grant to a foundation controlled by the Realtors.
A familiar face
The single biggest scandal during Gilzean’s tenure as district administrator at the Central Florida Tourism Oversight District came when Gilzean attempted to give a lucrative contract to Figgers Communications. That’s a telecom company run by Freddie Figgers, a Ron DeSantis donor who is one of the governor’s appointees to the Florida Commission on Ethics (a board to which DeSantis once appointed Gilzean, as well.)
The backlash to the no-bid deal was so severe that the tourism district and Figgers ended up canceling it.
But Gilzean helped find new business for Figgers’ company once Gilzean took control of the Orange County elections office.
Specifically, in August, Gilzean’s office awarded a $275,000 grant to CareerSource Central Florida, a regional skills-training and job-placement agency.
The grant was to fund an adult internship program. But the agreement included an unusual provision.
Under a clause titled “Bridging the Digital Divide,” the agreement compelled CareerSource to buy all electronics and cell service from “a Florida-based telecommunications company that is minority-owned and specializes in manufacturing consumer electronics and business laptops.”
In a statement to Seeking Rents, CareerSource Central Florida said that the Supervisor of Election’s Office proposed that provision. And while no individual vendor is spelled out in the contract, the agency said Gilzean’s office specifically recommended Figgers Communications.
CareerSource said it subsequently spent nearly $56,000 to buy 60 tablet computers from the company. The agency chose Figgers over cheaper quotes from both Apple and Samsung, partly, the agency said, because Figgers offered to include a digital literacy course and a year of Internet service with its devices.
CareerSource has since agreed to return the $275,000 to the Orange County SOE amid the uproar around Gilzean’s spending. The agency said it is instead using funding from other programs to cover the cost of the tablets it bought from Figgers.
It’s not clear whether Gilzean ever urged other SOE contractors or grantees to do business with Figgers Communications. Freddie Figgers did not respond to requests for comment.
Gilzean’s office also made at least one payment directly to Freddie Figgers’ company. The office’s check register shows a roughly $6,600 payment to Figgers Communications in December.
A spokesperson for Castor Dentel said the payment was for five broadband modems. They ended up going unused.
Under cover of a hurricane
In at least one case, Gilzean used Hurricane Milton as a reason to hire another video-production company, apparently without any kind of public solicitation at all.
Hurricane Milton struck Florida on Oct. 9. Six days later, Gilzean issued a memo invoking emergency powers to bypass normal bidding rules and immediately begin purchasing services from Top Story Studios LLC. The company is owned by Jamie Holmes, a former television news anchor at WFTV, the ABC affiliate in Orlando.
“The urgent need for rapid and efficient communication was critical to ensuring public safety, voter education, and the continuity of essential election operations during and after the hurricane,” Gilzean wrote in the memo. “This expenditure and agreement were authorized under my a capacity as Supervisor of Elections, reflecting my commitment to transparency, operational continuity, and public service during emergencies.”
Records show Gilzean’s office ultimately paid $81,000 to Top Story Studios, which primarily produced a series of often self-promotional videos and graphics for Gilzean to use on the SOE’s various social-media channels.
One video, for instance, promoted an outreach program to veterans that featured video of Gilzean shaking hands with veterans and presiding over a press conference while stirring music played in the background. Another featured behind-the-scenes video of an interview Gilzean gave to a local TV show.
None of it had anything to do with Hurricane Milton, aside from a few minutes of footage in which Gilzean assured viewers that none of Orange County’s voting machines had been damaged in the storm and praised utility workers for quickly restoring power to the supervisor’s office.
Holmes did not respond to requests for comment.
Republicans on the payroll
Gilzean approved an assortment of payments to businesses and organizations linked to prominent Republican politicians and operatives.
For instance, Gilzean’s office awarded a $45,000 grant in September to the Orlando Regional Realtor Foundation. The award came a few months after the organization hired Republican state Rep. Susan Plasencia of Orlando as its executive director.
The foundation is the charitable arm of of the Orlando Regional Realtors Association, a real-estate industry group that lobbies local elected officials and state lawmakers.
The grant, records show, is intended to fund a hodgepodge of activities and programs, including, voter registration tables during Orlando Regional Realtor events, recruitment of poll workers, and ad space in a Foundation newsletter.
After Karen Castor Dentel was elected, the Supervisor of Elections office asked the Realtors Foundation to cease work under the contract. But unlike CareerSource — and unlike Valencia College and the Central Florida Foundation, another civic group that got a large grant from Gilzean — it’s not clear if the Realtors Foundation will return any money to Orange County taxpayers.
“In September 2024, the Orlando Regional Realtor Foundation (ORRF) entered into an agreement with the Orange County Supervisor of Elections (OCSOE) to support nonpartisan voter outreach, education, and training efforts,” the foundation said in an emailed statement to Seeking Rents. “As part of this agreement, ORRF provided services leading up to the November 2024 election and we will continue to meet our obligations through September 2025.”
Gilzean’s office also paid more than $33,000 between September and December to Jones Walker, a law firm with offices in Tallahassee and Miami.
While the firm performed some legal work for the SOE, invoices show that much of the money paid for public relations support. More than half of the $33,000 paid for services from Andres Malave, who was the spokesperson for former state House Speaker Paul Renner (R-Palm Coast) before joining Jones Walker last summer as the firm’s director of government relations.
Invoices show Malave billed taxpayers $325-an-hour for services such as such as “pitching writing product to Orlando Sentinel,” arranging a call “to discuss the formation of an op-ed highlighting his youth initiative,” and coordinating with the Supervisor’s Office “to promote SOE successes in media.”
Malave did not respond to requests for comment.
In addition, the SOE made two payments totaling more than $8,500 in December to TMF Communications, a company run by Taryn Fenske, a former communications director under Ron DeSantis who also worked as a spokesperson for a Super PAC that supported DeSantis’ failed presidential campaign.
It’s not clear what Fenske did for Gilzean. The Supervisor of Elections office says it has no record of any contract with her company and invoices only refer to broad services around “strategic messaging and crisis management.”
Fenske, who also landed work from New College of Florida after DeSantis appointed a new slate of school leaders, did not respond to requests for comment.
Gilzean’s office also made a $3,710 payment in in August to “Top Flight Strategy,” a company that corporate records show is run by Eric Raimundo, an aide to state Sen. Keith Truenow (R-Tavares.)
An invoice says the payment was for yard signs of some kind. Raimundo did not respond to requests for comment.
And Gilzean approved a $2,000 payment in June to Ello Creative. That’s a marketing and graphic design company in Tallahassee run by Jordan Gibson, who was the digital director on Ron DeSantis’ 2022 gubernatorial campaign. Ello Creative’s clients have also included the Central Florida Tourism Oversight District.
Gibson said in an email that Gilzean hired her company to redesign the Supervisor of Elections logo and update other promotional materials.
“I have become a familiar name in the design and creative space due to my quick design turnaround,” Gibson said. “Orange County SOE contacted me for a quick-turnaround project to deliver a new seal, logos, banners, and updated print material — all for a considerable discount.”
Missing work
There are also a number of instances in which Gilzean awarded contracts under which it’s not clear what — if anything — happened.
For instance, in October — just before early voting began in Orange County — Gilzean’s office gave a one-year deal to Indelible Management Solutions to provide temporary staffing during the election.
Indelible is part of a state contractor with deep ties to the DeSantis administration. The company sponsored the governor’s 2022 inauguration, gave at least $100,000 to his 2024 presidential campaign, and counts a former DeSantis chief of staff among its lobbyists.
But the SOE’s new administration says it can find no record of any work provided by Indelible. Nor can it find any records of payments to the company.
Executives at Indelible did not respond to requests for comment.
Similarly, Gilzean gave a legal services contract in September to Siplin Law. That’s an Orlando law firm run by Gary Siplin, a controversial former state senator. Siplin served in Tallahassee as a Democrat but more recently donated to DeSantis’ presidential campaign.
But again, the Supervisor of Elections office says it can find no record of any work by, or payments to, Siplin’s firm. Siplin did not respond to requests for comment.
Some of it may be simple sloppiness.
Yet another marketing-related contract handed out under Gilzean went to Crown Communication Group, a firm run by Ericka Dunlap, a prominent public-relations strategist and former Orlando City Council candidate. But as with Indelible and Siplin, the SOE never made any payments to Crown Communication under the deal.
In an email, Dunlap said that Gilzean’s office awarded her company a contract in September. But Dunlap said she wasn’t actually notified of the award until October. And she said there weren’t any discussions about “next steps” until December — just before Gilzean left office.
“This delay in communication was unexpected,” Dunlap said in the email. “Consequently, while we are prepared and eager to commence work, we have not yet undertaken any tasks for the OCSOE due to the lack of clear directives following the award notification.”
OH-MY-GOD!! This story is yet another shining example of the grift that Republicans in the "FREE TO GRIFT" state of Florida are doing with our tax money. It's no wonder why there is little money for Education!!
Spoiler alert: NONE OF IT IS SIMPLE SLOPPINESS! It’s all a deliberate grift at every turn.