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Jones outspent rivals in bid for Winter Garden District 2 commission seat

The developer/construction exec spent nearly as much as Winter Garden's four other candidates combined. 

Fistful of hundred dollar bills
Iliana R. Jones is her campaign's biggest funder. Research shows that the more personal money a candidate pours into their race, the less likely they are to win. Photo: Fotomaster

Iliana R. Jones has dropped some serious cash in her quest for the District 2 seat on Winter Garden’s city commission. 

According to campaign finance reports, obtained via public records request, Jones has laid out  more than $21,000 on her city commission bid to date, making the 2024 District 2 race one of Winter Garden's spendiest. 

Jones drew 48 percent of the vote March 19 — not quite the 50 percent required to win the election outright, so she is in a run-off against incumbent Commissioner Ron Mueller who pulled 41.9 percent of the vote. The election is April 16. Early voting began Monday (8 a.m. to 5 p.m.) and will run through Friday at the Orange County Supervisor of Elections office at 119 Kaley Street in Orlando.

Jones has largely funded her own campaign. While campaign finance reports indicate that the co-owner of Empire Development and Empire Finish Systems, netted $28,789 in contributions, $18,575 came directly from Jones herself. She seeded her campaign with donations of $575 and $3,000 in October and November, before infusing it with $10,000 in mid-December. She donated another $5,000 to her own campaign at the end of February. 

Jones, who ran against Mueller in 2021 and lost by just 66 votes, has put down more than $20,000 on marketing products and advertising, including $4,334.62 on campaign T-shirts and $16,232.65 on what her campaign finance forms lists simply as “advertising.”

Iliana Jones at Winter Garden MLK celebration
Iliana R. Jones at Winter Garden's Martin Luther King, Jr. event. She spent $20K-plus on marketing and advertising, like campaign T-shirts.

That figure includes $3,070.36 to Millennium Consulting Inc., the marquee political marketing and public relations firm operated by Edgewater Mayor and political consultant John Dowless. According to its website, the firm, which provides a wide range of services from general campaign consulting to opposition research, has worked with the Republican Party of Florida, the Republican National Committee and scores of politicians running for everything from Congress and the State House to school boards and town councils.

Dowless is consulting on Austin Arthur’s county commission campaign. Campaign finance reports show that Millennium Consulting also assisted the two other members of Arthur and Jones' political foursome — her brother, Oakland Commissioner Sal Ramos, and Chloe Johnson, sworn in Thursday as District 3 Commissioner.

The city commissioner job pays $7,200 a year. That means Jones spent nearly three times what she would earn in the job to pursue the job. And she spent almost as much as her opponents and the District 3 candidates combined. 

District 2 Commissioner Ron Mueller. He donated $1,010 to his own campaign.

Mueller, who collected $6,125 in donations, has spent $2,194 on his campaign to date, according to campaign finance records. Danny “DJ” Culberson, who brought in close to $12,000 in donations, spent $10,762 before getting knocked out of the race in the March 19 regular election. In the District 3 race, Karen Mcneil's campaign expenses totaled $4,760 while Johnson spent $5,501. Mcneil donated $140 and Johnson contributed $125 to their respective campaigns.

It’s not unusual for candidates to spend big to win political office, according to longtime Florida election observer Aubrey Jewett, PhD, assistant director of University of Central Florida’s School of Politics, Security and International Affairs.

From a purely financial, return on investment point of view, “it makes very little sense,” he said in an email. But he added, “Some candidates really want to win the election and serve in the office and if they have the money they are willing to spend it.” He points to Republican Sen. Rick Scott, who spent $75 million of his personal fortune to win his first term as Florida governor in 2010 and another $63.6 million of his own money to secure his Senate seat.

“Their motive to serve is clearly not the salary, but instead is presumably because they think they will do the best job and they probably have an agenda that they want to implement and perhaps also have a little bit of pride involved as well (if they are running, they are running to win, not to lose - they want the title)," Jewett said.

But while top-spending candidates typically win, self-funders historically do not, according to the Center for Responsive Politics. Of the 44 candidates who spent more than $1 million of their own fortunes on House and Senate races in 2022, just six won. In 2020, there were nine winners out of the 36 candidates who bankrolled at least $1 million of their campaigns. In 2016, five of 23 self-funders won. 

Political scientist Jennifer Steen, author of Self-Financed Candidates in Congressional Elections (University of Michigan Press, 2006) found an inverse proportion to self-funding campaigns and winning elections. She wrote, “a candidate's chance of winning a primary or general election tends to decrease as the amount of personal funds invested in their campaigns increases." 

Meaning, the more of their own cash a candidate pours into their campaign, the less likely they are to actually win. 

Jewett said there are a couple of reasons for this. “Candidates that are able to raise money from a lot of people are demonstrating support for their candidacy,” he wrote in a separate email. “The people that attend fundraisers and are willing to give money are more passionate and also more likely to show up and vote and to talk up the candidate to their friends and neighbors, which increases support. Self-funding candidates by contrast usually do not engage potential supporters as much in this manner and thus end up having fewer actual voters.”

Jewett added that self-funders also “open themselves up to charges of trying to ‘buy the election,’” which may resonate with voters. 

After herself, Jones’ biggest donor is the family behind Jack Jennings & Sons, a “high volume commercial construction firm” in Orlando. Founded in 1948, the company has built numerous Orange County structures: churches, apartment complexes, clubhouses, office buildings, student housing at University of Central Florida, even a jail. Its board of directors is chaired by former company president Toni Jennings, who served as Florida’s Republican lieutenant governor from 2003 to 2007 — the first woman in that role. 

Jennings family members donated a total of $6,000 to Jones’ campaign, making six separate $1,000 donations, the maximum an individual can donate. Jennings family members also made six individual $1,000 donations to Jones' brother, former Commissioner Sal Ramos, for his unsuccessful mayoral bid. 

Jones’ campaign has 10 additional individual donors, according to campaign finance reports, including Ramos who gave his sister $1,000.  

Mueller, who contributed just $1,010 of his own money to his campaign, has 33 individual donors, plus one commercial donor. Main Street Collision, which chipped in $500, is the company Mueller partnered with to secure a car for a constituent whose vehicle was repossessed on Christmas Eve.


Lucy Dillon and Andrea Charur contributed to this report. 


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