Jesse Phillips, alleged author of bill that would give mayor more power, now running for mayor

Jesse Phillips, who co-founded a group that has targeted and helped oust every city commission member over the last two election cycles, has officially filed to run for mayor of Winter Springs in 2026. 

Phillips, the cofounder of the Winter Springs Community Association and former vice chair of the Republican Party of Florida, will face off against incumbent mayor Kevin McCann in a November race that could be consequential for the future of the mayor’s role. 

Phillips said his announcement will not change anything about his role with the Winter Springs Community Association, where he writes opinion pieces, routinely lobs political attacks, and emails its members regularly. The group calls itself a grassroots advocacy organization, but critics say it crosses a line and endorses candidates; the group has in the past hosted political candidate town hall forums specifically for candidates it endorsed.  

“The community association has done a great job highlighting some of the problems that the city has denied over the years,” Phillips said. “I think a difference would be (that) my candidacy is going to focus more on solutions, whereas the role over the last number of years that the [Winter Springs Community Association] played was to build consensus on the need for change.”

McCann has already filed to run for reelection, and said he recently held a fundraiser that raised just over $5,000. McCann said he has no problem with having an opponent – but said there will be clear differences between the candidates. 

“It’s going to be, I suspect, one of the more expensive races in Winter Springs history,” McCann said. “I hear that there will be a great deal of money coming from outside of Winter Springs entering this race. I am concerned that it looks like there will be a great deal of special interest from outside the city.” 

In 2022, Commissioner Victoria Bruce reported raising more than $70,000 to defeat incumbent City Commissioner Kevin Cannon. 

Phillips does not yet have a campaign website. Oviedo Community News has a candidate guide for the 2026 election here, which will update throughout election season, including to reflect Phillips’ candidacy. 

Redefining what the mayor of Winter Springs’ role could be going forward

Phillips was widely known to be planning a run for mayor, but his candidacy wasn’t official until last week. 

But Phillips’ role in local politics goes further than just a run for office. Last October, Phillips was listed as the author of a draft bill to expand the powers of the mayor by an act of the Legislature. Currently, there are five voting city commissioners, and the mayor only votes in the rare case of a tie. The bill was pushed by legislators for more than 3 months. Rep. Rachel Plakon, who filed the bill, has since said she won’t be pushing for its passage this session.

The goal, laid out in the bill, was to make the Winter Springs mayor a voting member of the City Commission, and then eliminate one City Commission seat by 2028.

Critics of the bill, though, were concerned that the mayor could also be given the ability to hire and fire staff with a simple majority vote of the Winter Springs City Commission. 

“The bill provides that the mayor, who previously had no administrative authority, now has administrative authority over city employees as provided by city charter or ordinance,” an analysis of the bill reads. 

Plakon, who introduced the bill, said it was “no longer needed” after the Winter Springs City Commission this month moved to create its first Charter Review Commission in 16 years.

The bill could come up again during a future legislative session, especially given that one key opponent of the bill – Rep. David Smith of Winter Springs – is term-limited and won’t  be in the Legislature in 2026. Winter Springs’ own Charter Review Commission is also expected to consider how the role of mayor should be structured going forward. 

Phillips said the timing to announce his run did not coincide with the defeat of HB 4083.

“No,” Phillips said. “The bill in Tallahassee is still in process through that legislative session. I mean, Rachel (Plakon) has said she’s not going to bring it up, but we do have a charter review coming.”

Past politics

Phillips has been tied to a proposal in 2020 to swap rural land for Chris Dorworth’s proposed River Cross Development. The Orlando Sentinel reported that a mailer sent out encouraging residents to tell county commissioners to “support the swap” was linked with Phillips. 

“At no time did I urge any commissioner to do anything about any proposed swap,” Phillips told the Orlando Sentinel in 2021. “(I was) neither paid by Dorworth or otherwise. I allowed my P.O. Box to be used for my in-laws and their neighbors to send their petitions to help save the area near their farm and preserve the rural area and decrease density inside the rural boundary line.”

That attack – that Phillips has links to developers – consistently comes up from his critics. Phillips pointed to his opposition to an early proposal to build a Super Walmart near the Tuscawilla neighborhood. 

Rumors about the Walmart sparked packed community meetings in 2022, and likely contributed to then-Deputy Mayor Kevin Cannon’s defeat that year. Cannon had argued that approving a Walmart-type development was not legally possible given the development rules in place, and the development was never formally proposed to the city government in 2022 or subsequently.

“I would fight any bad development that tries to come into our city in the same way that I’ve already done,” Phillips said. 

“You have to look at the code and what’s legally allowed,”  Phillips continued, defining what he sees as a “bad” development. “You have to look at density and what kind of traffic is going to be added and whether what’s coming in adds a value to our community or takes away from it. You have to look at our capacity – can we handle any more development?”

Candidate profile information for Winter Springs mayor

Who is Jesse Phillips?

Phillips is the son of a retired preacher, and Phillips is also a former pastor at Redeemer Church in Winter Park.

Phillips first ran for office in 2014, for a seat in the Florida House of Representatives. At the time he was working as director of information technology at Orlando Orthopaedic Center, a role he’d had since 2012.

In that campaign, for House District 49, he raised $6,135. Phillips filed his candidate application in March 2014, but withdrew in June. He said that after being laid off from his job at Orlando Orthopaedic Center, he needed to focus on finding employment. 

That wasn’t the only stumbling block, though. “I would have had to move into the district, which we were thinking of at the time anyway,” Phillips said. Phillips is married to wife Rebekah and has four children.

Ultimately, the seat was won by Rene “Coach P” Plasensia. Phillips is now a managing partner at ProVision Technology Solutions, an IT support company owned by his family.  

In 2017, Phillips was elected as state committeeman for the Seminole County Republican Party, a position he still holds today. In 2021, he applied unsuccessfully to be the interim mayor of Winter Springs after mayor Charles Lacey resigned; McCann was ultimately chosen by the Winter Springs City Commission as interim mayor. 

Phillips also worked on campaigns for Bob Cortes for Florida House of Representatives in 2014 and Sammy Gibson for Seminole County clerk of court in 2017. 

In 2024, Phillips was elected vice chairman of the Republican Party of Florida over a candidate endorsed by President Donald Trump. 

Phillips lost his re-election bid for vice chair of the Republican Party of Florida in 2025 by a vote of 130-70 to Jovanté Teague, a corrections officer. Teague, it was later reported, had been convicted in 2019 in an investigation into an alleged sexual relationship with an inmate, and had to surrender his criminal justice certification, making him ineligible to work in law enforcement. 

Phillips told reporters that the conviction wasn’t known whenTeague campaigned against him.

Who is Kevin McCann?

Elected as Winter Springs mayor in 2022, McCann had previously been president of the Tuscawilla Homeowners Association and vice chairman of the Winter Springs Planning and Zoning Board.

Professionally, he earned a degree in social work and worked in that field in Delaware before starting work in the hospitality industry. He became a partner in three different restaurant ventures, including Johnny’s Fillin’ Station and Johnny’s Other Side.

Registered as a republican, McCann has worked to build consensus within the city commission and on city staff, calling for “turning down the temperature” during heated political moments and openly working to bolster city staff morale as attacks against commissioners and staff on social media had become more frequent.  

McCann is married to his wife, Katherine and has two children.

In an email to OCN McCann said his platform consists of listening to residents and putting them first, protecting Winter Springs neighborhoods, preserving its environment and tree canopy, and planning responsibly for the future. He said he believes “Winter Springs should grow thoughtfully, protect what makes us special, and remain a place families are proud to call home.”

Abe Aboraya is a Report for America corps member.