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[Opinion] Why Are We So Glued to the City of Orlando’s District 5 City Council Race?
ORLANDO, Fla. (FNN NEWS) – If you’re like many Orlando politicos, you’re aware of the Orlando City Council race that has been getting attention since 2014 in Orlando City Council District 5. In 2014, now Orlando City Councilwoman Regina Hill (below) successfully and surprisingly unseated four-term community staple Daisy Lynum…well she annointed her son Juan to carry on the Lynum legacy …but… that plan crumbled like an over cooked cookie. (In fairness, it’s important to acknowledge that I helped on the Hill campaign as a volunteer.) With that acknowledgement, I am still amazed this particular race is already heating up as the Commissioner seeks re-election. But why exactly are so many that can’t even vote in the district interested in its players and outcome? Well, it comes down to the Commissioner’s personal life, the unique group of nontraditional opponents she has and why they are suggesting they can unseat her.
City of Orlando District 5 Commissioner Regina I. Hill. (Photo courtesy of her Facebook page)
Almost as soon as Commissioner Hill was elected, some familiar faces predicted her doom and suggested everything from removing her from office to asking her to resign. Commissioner Hill illustrated to all during her initial campaign bid, and after getting into office, that she is a fighter and is willing to go the extra mile for her constituents.
Sadly, however, some of the Commissioner’s challenges slowly entered into her newly elected position. Nearly immediately, her aide was involved in turmoil after a drunken interaction at a local movie theater. Then came the rumor the Commissioner was removed from a comedy club for being drunk and disorderly. It would not be long until the Commissioner’s children were involved, and ultimately exonerated, from drug trafficking allegations. There were even questions over whether her home actually was in the district. If all that wasn’t enough, sadly her daughter was murdered while visiting Tallahassee, taking the Commissioner from being a grandparent to a parent again overnight. But outside of the staffing issue, these issues are all part of her personal life.
We all have struggles and ups and downs, so while it might be popular to point out these challenges as the bases to want to see someone new in the office…not so fast.
You see, one thing I learned while working on the Commissioner’s campaign in 2013 was that District 5’s constituents have a unique perspective to how they vote for and support candidates and those in office. What might traditionally be a disaster for a candidate or elected official in another area of town didn’t seem to matter as much to District 5 voters. I recall a gentleman stopping me the night of Hill’s watch event in which she learned she made it into a run-off with Commissioner Lynum’s son, Juan Lynum. Somehow the gentleman got on the topic as to whether the Commissioner’s past glances with the law, 21 of them to be exact, would interfere with her chance of winning. I remember his response to this day: “Randy, you need to understand something. Being black and living in Parramore is something you’ll never understand. We all know someone that’s been touched by drugs, crime or by the law. It’s a way of life there. Regina is going to win this race.”
Commissioner Hill was eventually elected indeed defying all traditional logic. Not because she hadn’t worked hard or because we were tired of a career politician–certainly both points entered into the equation–but District 5 decided that her history and brazes with the law didn’t matter in ways most of us would think it would. You won’t find a candidate that works any harder. That said, let’s now explore the candidates in the race to unseat the one-term Commissioner and the likelihood of their efforts.
ERICKA DUNLAP
Ericka Dunlap (photo courtesy of her Facebook page)
Ericka Dunlap is most known as the first black Miss Florida and the 2004 Miss America. Dunlap grew up in the community of Carver Shores in a family with deep roots in the community. Her father, who passed away a few years back, owned a family roofing business. I met Dunlap in 2013, ironically just around the time I was introduced to Commissioner Hill. Their backgrounds couldn’t be more different.
Dunlap is a Boone High graduate and a graduate of the University of Central Florida, which is when she cut her teeth in the pageant world also being crowned Miss Orlando. Many don’t realize this, but the difference between Miss USA and Miss America is that the Miss America Pageant is heavily weighed on talent. It just so happens Dunlap has the brains and beauty to match her ability to sing ….wait for it … country music. I originally contacted Dunlap when I was launching a domestic abuse fundraising and awareness program, “Walk a Mile in Her Shoes,” for Harbor House, a local shelter and safe haven for women, men, children and pets in Orlando. Dunlap had recently returned from Nashville where she unsuccessfully attempted to launch a career in country music. Divorced and looking to reinvent herself, the timing was ripe to come home to Orlando and kick start her life again. While working with Dunlap to promote the domestic abuse awareness event, I recall our discussion about whether she might one day run for office. Dunlap’s family had a substantial history with the Lynum family, so she said “someday,” suggesting her loyalty to the Lynum family was more important than running for office against them.
I remember our visiting with Orlando Mayor Buddy Dyer during our tour promoting “Walk a Mile” and his hope to somehow find a fit for Dunlap, at the time, possibly as an Ambassador for the University of Central Florida. I mean, think about it: hometown girl graduates from UCF, wins Miss America, comes home to help her alma matter. You couldn’t ask for a better story. My prediction, at this stage of the process with Dunlap now an announced candidate supported by the Bracey legacy, the Mayor would really love to see Dunlap in the role of Commissioner. So while I’m unaware of any “official” endorsement, whether quiet or announced, you can be assured the Mayor is certainly a fan of Dunlap. It’s clear, as well, that Dunlap is off to a nice start in fundraising, which doesn’t necessarily translate to a win, but certainly doesn’t hurt.
JIBREEL ALI
Jibreel Ali (photo courtesy of his Facebook page)
My observations of Ali come at a distance from various interactions and political discussions on social media. His arsenal, or “secret weapon” in this race, rests not with him, but his family. He is the grandson of the former City of Orlando and Orange County Commissioner Mable Butler. Butler, royalty in local politics, continues to be a driving force in the community, most recently working to develop an affordable housing project in the Washington Shores community with her name on it, “Butler Preserve.” Ali has been utilizing his grandmother, in various social media videos, in which they talk about the history of the community and his running for office. But that’s not all he has working for him, as his mother-in-law is long-term Orange County School Board member Kathleen “Kat” Gordon. Gordon too has a long legacy of working hard for her community and certainly carries family clout to the race. Uniquely, however, Gordon has been relatively silent on her son-in-law’s inaugural entry into politics. Ali’s biggest challenge, in addition to fundraising, thus far seems to be his inability to put out clean and clear communications pieces.
Ali came out quickly to point out Dunlap’s lack of direct connection to the community in the very first District 5 forum a few weeks back, possibly tipping his hat too soon as to his strategy to trip the former beauty queen. Uniquely, during the same debate we saw a quick reaction from Dunlap towards Ali and others, including the current Commissioner, regarding their attack. She may be a former Miss America, but I’ve also witnessed the receiving end of her direct tone. Don’t anyone get it twisted, Dunlap too is a fighter and clearly ready to put on the boxing gloves when push comes to shove in running for this office. Remember, she’s a fierce competitor and skilled in public relations.
CYNTHIA HARRIS
Cynthia Harris (photo courtesy of her Facebook page)
Harris comes into yet another run for this seat quiet and a bit timid. While she seems to gain some attention, my observation of her in 2013-14 and now remains the same: she simply doesn’t seem to be able to provide deep rooted solutions to her suggestions of the district needing more jobs and affordable housing. While that messaging might resonate for any community, I think the debate last week made her inability to compete with the other players pretty clear. She simply doesn’t have the bandwidth to be competitive and probably would be better suited to align with one of the other candidates if she truly wants to be part of unseating Commissioner Hill.
SO THOSE ARE THE CANDIDATES. WHY THE INTEREST?
Chardwick Hardee, Vice Chairman of the Orange County Republican Executive Committee, recently told FNN News: “People love their community. And Districts 1-6 are all part of the community. No community rises when one falls. Therefore the success of District 5 is important to all of Orlando.” While Hardee, a former candidate for Orange County School Board, makes a point, there’s also the sheer drama of the race as it plays out on Facebook that draws attention.
National FOX News commentator and political strategist Tezlyn Figaro, who was Hill’s Director of Communications on her first winning campaign is so far not supporting any one candidate. Yet, she has created a Facebook page that lights up occasionally with unexpected drama, “Orlando City Commissioner D5 race commentary.” Originally created for political strategist and communication commentator discussions, the page has quickly morphed into a place where people are, at times, heavily debating the race. Not surprisingly only the incumbent seems to feel the page is worthy of discussion, which I believe is a fatal mistake on the part of Hill’s opponents. The Lynums made the same mistake in 2014 regarding social media, ignoring it as an influencer, leaving many of us and Commissioner Hill the open field of controlling the narrative to her benefit.
Not everyone is excited about Commissioner Hill heading towards a reelection bid and have made it no secret. Recently, a video of a clearly inebriated Hill surfaced and was shared frequently with the hashtag “#ResignReginaResign.” Yet, when you go back to my original analysis and discussion of how the Commissioner won in 2014, even with her baggage, will the anger of some be enough to keep her from reelection? Hill lost most of her support base, as related to key campaign volunteers, after being sworn in. Many felt she quickly sold out to the establishment and became known for not returning phone calls or communicating with those that got her elected. Then again, at least for me, I never expected much in return. Some believed there might be financial gain from her being in the office. But as I understand it, few if any saw financial benefits in the form of contracts and such.
The fascination with this race comes from so many different angles, but here’s the most obvious draw: It’s like a reality show without the cameras. You’ve got an outspoken no-holds-barred Commissioner with a record, the beauty queen with an edge, the family legacy candidate, and then some other folks who so far can’t find a way to be very memorable. It’s no secret unseating an incumbent is tough work. Commissioner Hill, despite her personal ups and downs, has been very public in the work she has done for her district, utilizing social media like a pro. The Commissioner’s personal challenges aren’t keeping her from fundraising either with a steady and notable stream of contributions coming her way.
Additionally, District 5 has the new Orlando City Soccer Stadium, the new Orlando Magic nighttime entertainment venue as well as a push for more affordable housing, so it’s of great importance to everyone who lives in Orlando, but especially in District 5.
While it’s far too soon to make a prediction on what the outcome will be of the November 7th election, if Commissioner Hill’s opponents don’t quickly define and separate themselves from why they are a better choice than her, my thoughts are Commissioner Hill wins maybe outright. If Dunlap or Ali can pull Hill into a run-off, one of them will win. November is a lifetime away in politics, so anything is possible. It’s much easier to determine who loses than who will win this one with possibly as few as 2,000 votes deciding the Commission seat. Grab your popcorn and adult beverage folks. This is going to be an interesting race to watch over the summer and into the fall.
________________________________________________
Randy Ross is a political contributor for Florida National News. | news@floridanationalnews.com
Florida
Byron Donalds Secures Endorsement From Gainesville Democrat Cynthia Moore Chestnut, Spotlighting Cross-Party Politics
Longtime Democratic leader backs Republican nominee as state Sen. LaVon Bracy Davis pushes back, renewing debate over the impact of cross-party endorsements in Florida politics
GAINESVILLE, Fla. (FNN) — Republican gubernatorial nominee Byron Donalds has secured the endorsement of Gainesville City Commissioner Cynthia Moore Chestnut, a longtime Democrat and former state lawmaker, drawing criticism from fellow Democrats and putting Florida’s history of cross-party political support in the spotlight.
Proud to have the endorsement of Cynthia Moore Chestnut, a longtime public servant who has represented her community at the city, county, and state levels.
I’m honored to have her support as our movement continues to grow across Florida! pic.twitter.com/r0oARJB15o
— Byron Donalds (@ByronDonalds) September 3, 2026
Chestnut announced her support for Donalds on Thursday and followed with a lengthy explanation defending her decision. She said she remains a Democrat but does not believe party affiliation should dictate her vote.
“My endorsement of Byron Donalds is not a betrayal of my values; it is a declaration that Black voters are not political property,” Chestnut wrote.
Chestnut, a former Florida House member, Alachua County commissioner and Democratic Party leader, said she wants to see Florida elect a Black governor in her lifetime.
That gives the endorsement additional historical significance. Donalds, who won the Republican nomination in Florida’s Aug. 18 primary, is seeking to become Florida’s first Black governor, according to The Associated Press.
The endorsement is also notable because Chestnut previously supported Democratic gubernatorial nominee David Jolly before shifting her support to his Republican opponent. Current reporting confirms Chestnut’s endorsement and her subsequent defense of the decision.
Florida Democratic state Sen. LaVon Bracy Davis, who represents Central Florida in the Florida Senate.
State Sen. LaVon Bracy Davis Pushes Back on Donalds Endorsement
Democratic state Sen. LaVon Bracy Davis of Ocoee responded with an extensive public statement saying she was “deeply disappointed” by Chestnut’s decision.
Bracy Davis focused much of her criticism on Donalds’ record on voting rights, including his opposition to federal voting-rights legislation and to the proposed Harry T. and Harriette V. Moore Florida Voting Rights Act, which Bracy Davis sponsors.
“I want to see a Black governor of Florida in my lifetime too,” Bracy Davis wrote, while arguing that representation should not be separated from a candidate’s voting record and policy positions.
The disagreement presents competing views of political independence. Chestnut argues that Black voters should not be treated as the political property of either party. Bracy Davis argues that representation should be weighed against a candidate’s record and policies.
Byron Donalds’ Jim Crow Remarks Resurface
Bracy Davis also invoked Donalds’ controversial 2024 comments about Black families during the Jim Crow era.
Donalds said at a Philadelphia event that “during Jim Crow, the Black family was together” while discussing marriage and family structure. Democrats sharply criticized the remarks, while Donalds rejected interpretations that he was praising segregation.
The distinction is important: Donalds did not explicitly say Black Americans were better off under Jim Crow.
Cynthia Moore Chestnut Points to FAMU and Black Representation
Chestnut also cited Donalds’ connection to Florida A&M University and the importance she places on Black representation.
Donalds attended FAMU before transferring to Florida State University, where he earned his bachelor’s degree.
Chestnut, a FAMU graduate, said she respects Donalds’ support for historically Black colleges and universities and also cited shared cultural connections through his Jamaican and Panamanian family background.
Bracy Davis countered that attending an HBCU should not substitute for examining a candidate’s political record.
David Jolly, a former Republican congressman who became a Democrat in 2025, is the Democratic nominee for governor of Florida in 2026. Source David Jolly
David Jolly Was a Republican Before Becoming a Democrat in 2025
Party affiliation adds another dimension to the controversy.
Democratic gubernatorial nominee David Jolly represented Florida in Congress as a Republican from 2014 to 2017. He left the Republican Party in 2018 and became an independent.
Jolly remained unaffiliated for several years before registering as a Democrat in April 2025, as he considered entering the 2026 governor’s race.
He subsequently entered the race and won the Democratic nomination in the Aug. 18 primary. AP described the contest as Donalds, the Republican nominee, against Jolly, a former Republican congressman running as the Democratic nominee.
The circumstances differ from Chestnut’s decision: Jolly formally changed parties; Chestnut says she remains a Democrat while supporting the Republican nominee.
The history nevertheless creates an unusual political contrast: a longtime Democrat is supporting Donalds over a Democratic nominee who previously represented Florida in Congress as a Republican.
Byron Donalds Adds $1 Million From Orlando-Based Morgan & Morgan
Chestnut’s endorsement comes as Donalds continues attracting substantial financial support heading into the general election.
A Florida National News review of Florida Division of Elections campaign-finance records found that Morgan & Morgan contributed $1 million to Friends of Byron Donalds PAC on Aug. 26, 2026.
The contribution appears in the committee’s 2026 G1A report and identifies the contributor as “Morgan & Morgan,” with an address at 20 N. Orange Ave., 16th Floor, Orlando.
The same report shows 18 contributions totaling approximately $1.93 million, meaning the Morgan & Morgan contribution accounted for more than half of the money listed in that group of contributions.
Morgan & Morgan was founded by Orlando attorney John Morgan, who has a long history of political involvement and support for Democratic candidates and causes, although his political activity has crossed party lines.
The distinction is important: Florida’s filing identifies Morgan & Morgan — not John Morgan personally — as the contributor of the $1 million.
For Donalds, the developments represent two different forms of support as the general election takes shape: a seven-figure contribution from a prominent Orlando law firm and a cross-party endorsement from a Democratic elected official with decades of experience in Florida politics.
Democratic Orlando Mayor Buddy Dyer included Republican Steve Leary among his endorsed candidates for the 2024 election. The Orlando PAC mailer promoted Leary for Orange County Commission District 5 alongside several Democratic candidates. Source Winter Park Voice
Buddy Dyer, Gary Siplin and Victoria Siplin Show Cross-Party Support Is Not New
Chestnut’s decision has generated attention, but Democratic elected officials supporting Republican candidates is not unprecedented in Central Florida.
During the 2024 Orange County Commission District 5 race, Democratic Orlando Mayor Buddy Dyer endorsed Republican former Winter Park Mayor Steve Leary.
Political Rivals: Samuel Vilchez Santiago lost the 2020 Florida House District 48 Democratic primary to Daisy Morales, who went on to win the seat. During Morales’ 2022 reelection campaign, Vilchez Santiago supported Rita Harris, who defeated Morales in the Democratic primary. Vilchez Santiago later chaired the Orange County Democratic Party during the 2024 dispute over Morales’ party status. In their 2026 House District 43 rematch, the dispute resurfaced in news coverage and FHDCC attack mailers alleging Morales endorsed Republicans and was expelled from the local party. The mailers identified the Florida House Democratic Campaign Committee as the payer and Vilchez Santiago as approving them. Morales disputes the allegations and has challenged them through litigation and an election complaint.
Samuel Vilchez Santiago, then-chairman of the Orange County Democratic Executive Committee, told Winter Park Voice that the organization “sent out texts and mailers alerting voters that Leary is a Republican, not a Democrat.” Vilchez Santiago said those communications were not issued in response to Dyer’s endorsement, but were intended to educate voters.
However, former Democratic state Sen. Gary Siplin and Orange County Commissioner Victoria Siplin, also a Democrat, supported Leary as well.
Those endorsements occurred in an officially nonpartisan county election, an important distinction from the partisan governor’s race, although the candidates’ political affiliations were publicly known.
The examples nevertheless demonstrate that prominent Central Florida Democrats have previously crossed party lines to support Republican candidates.
Then-Orange County School Board Vice Chair Angie Gallo publicly endorses Joel Montilla for Orange County Commission District 5 in a campaign graphic paid for and approved by Montilla’s campaign. Source: Joel Montilla Campaign
Angie Gallo Endorsed Republican Joel Montilla and Served as His Campaign Manager
Another example emerged during the same 2024 Orange County Commission election.
Angie Gallo, an elected Orange County School Board member who served as board vice chair, publicly endorsed Republican Joel Montilla during his campaign for the District 5 commission seat.
Her involvement extended beyond an endorsement.
A Joel Montilla campaign press release dated Oct. 24, 2023, identifies “Angie Gallo — Campaign Manager” in the campaign’s contact information, providing direct campaign documentation of her role.
The campaign subsequently publicized Gallo’s endorsement of Montilla.
The distinction is significant: the documentary record establishes both a formal campaign-management role and a public endorsement.
The Orange County Commission race was officially nonpartisan, although Montilla’s Republican affiliation was publicly known.
Gallo’s involvement provides additional context for questions about when cross-party political activity becomes subject to internal Democratic Party rules.
Rep. Yvonne Hayes Hinson, D-Gainesville, Rep. Daisy Morales, D-Orlando, Rep. Tray McCurdy, D-Orlando (in front) and Rep. Angie Nixon, D-Jacksonville, protest on the Florida Seal as debate is halted in the House of Representatives Thursday, April 21, 2022, at the Capitol in Tallahassee, Fla. The session was halted by the protest, but continued after a brief recess. Phil Sears AP
Former Democratic State Rep. Daisy Morales Adds Context to Party-Loyalty Debate
Former Orlando state Rep. Daisy Morales, a Puerto Rican Democrat, provides another Central Florida example relevant to the debate over party loyalty and political independence.
In 2022, Morales, a Puerto Rican lawmaker known for working across party lines, represented a Central Florida district with a significant Puerto Rican population.
On April 21, 2022, Morales joined Black Democratic lawmakers protesting a congressional redistricting map backed by Republican Gov. Ron DeSantis on the Florida House floor.
The demonstration received state and national attention.
The Miami Herald reported that several Black Democrats disrupted debate and that Democratic lawmakers sang “We Shall Overcome,” temporarily forcing the House into recess.
The Herald identified Morales alongside Democratic Reps. Yvonne Hinson, Travaris McCurdy and Angie Nixon in its reporting and accompanying photograph.
Morales carried a sign declaring:
“Legislators serve the people. Not your party.”
The Herald reported that McCurdy, Nixon and Rep. Felicia Robinson sat in the center aisle while more than a dozen Democratic colleagues gathered around them in solidarity. The Republican-controlled House later approved the congressional map 68-38 along party lines.
The demonstration also received national coverage.
NBC News, in reporting preserved through syndication, identified Morales as the Hispanic representative participating in the demonstration and subsequently issued a correction after initially identifying another lawmaker.
The episode placed Morales alongside Black Democratic lawmakers in one of the Legislature’s most visible protests of the 2022 congressional redistricting fight.
FNN also reported on the demonstration at the time, describing Democratic lawmakers as temporarily shutting down House proceedings while protesting the congressional map.
Two years later, Morales became involved in an Orange County Democratic Party dispute over an alleged loyalty-oath violation connected to the 2024 Orange County Commission District 5 election.
Morales disputes that she endorsed Republican Joel Montilla, maintaining that her involvement was limited to joining his campaign-launch host committee. Montilla has separately told FNN that Morales did not endorse him.
That creates a notable factual contrast with Gallo: Montilla’s own campaign documentation identifies Gallo as his campaign manager, and she subsequently publicly endorsed him.
The available record does not, however, establish that Morales and Gallo were subject to identical Democratic Party membership requirements, loyalty provisions or disciplinary authority.
Democratic state Rep. Jose Alvarez, center, speaks on the Florida House floor alongside Democratic state Rep. Susan Valdés, left, and Republican state Rep. Fabián Basabe, right. Source: Florida House
State Rep. Jose Alvarez Crossed Party Lines, Then Withdrew His Support
Cross-party support has also occurred in partisan legislative politics.
Democratic state Rep. Jose Alvarez of Kissimmee endorsed Republican state Rep. Fabián Basabe for reelection in 2025, saying his decision reflected his experience working with Basabe rather than their different party affiliations.
Alvarez later rescinded the endorsement in July 2026 and called for Basabe to resign following a civil jury verdict involving two former House employees.
The episode nevertheless provides another recent example of a Central Florida Democrat publicly supporting a Republican candidate.
Cross-Party Support and Democratic Party Discipline Are Different Questions
The examples involving Chestnut, Dyer, the Siplins, Gallo, Morales and Alvarez highlight an important distinction between cross-party political support and internal party discipline.
Being a registered Democrat or Democratic elected official does not necessarily make someone subject to the same county party loyalty oath, bylaws or disciplinary procedures.
That distinction is part of an unresolved dispute involving former state Rep. Daisy Morales, who filed a defamation lawsuit and sought a Florida Elections Commission investigation challenging campaign claims that she endorsed Republicans and was expelled from the Orange County Democratic Party. The allegations remain unresolved, and no finding of an election-law violation has been established.
The comparison with Angie Gallo is notable. The documentary record establishes Gallo’s formal role in Republican Joel Montilla’s campaign and her public endorsement, while Morales disputes endorsing Montilla — and Montilla has independently said Morales did not endorse him.
Whether the two were subject to the same party rules and disciplinary authority remains a separate factual question. Their situations can therefore be compared politically without assuming they constituted identical violations of Democratic Party rules.
Cynthia Moore Chestnut Says She Remains a Democrat
Chestnut has made clear that she does not consider supporting Donalds a departure from the Democratic Party.
“This endorsement does not mean I have stopped being a Democrat,” she wrote.
Instead, Chestnut framed her decision as an exercise of political independence and argued that Black voters should not be expected to support candidates solely on the basis of party affiliation.
Bracy Davis sees the endorsement differently, arguing that Donalds’ record on voting rights and other issues conflicts with principles Chestnut has advocated during decades in Democratic politics.
Their disagreement has transformed a single gubernatorial endorsement into a broader discussion about representation, party loyalty, policy and political identity.
What Comes Next: Will Other Democrats Follow Chestnut?
Chestnut’s endorsement now raises a broader question heading into the general election: Will other Democratic elected officials or longtime party leaders cross party lines and publicly support Donalds?
For now, Chestnut represents a notable individual endorsement rather than evidence of a broader Democratic movement toward the Republican nominee.
But the question carries added significance because of the historic nature of Donalds’ candidacy.
The Associated Press reported after the Aug. 18 primary that Donalds won the Republican nomination and is seeking to become Florida’s first Black governor. AP also placed Donalds among a historically significant group of Black major-party gubernatorial nominees running across the country in 2026.
Donalds has emphasized that winning the general election will require more than support from within his Republican base. After the primary, he told reporters that President Donald Trump’s endorsement was important but would not, by itself, carry him through the general election.
Chestnut has placed greater emphasis on the historic dimension. In explaining her endorsement, she explicitly cited her desire to see a Black governor of Florida during her lifetime.
That makes what happens next worth watching: whether Chestnut’s endorsement remains an individual cross-party decision or whether additional Democratic elected officials, party figures or other traditionally Democratic political supporters make similar choices before November.
The 2026 contest already presents an unusual political contrast: Donalds is seeking to become Florida’s first Black governor, while Jolly represented Florida in Congress as a Republican, left the GOP in 2018 and became a Democrat in 2025. Chestnut, a Democrat with decades of party involvement who says she remains one today, has chosen to support Donalds.
Whether other Democrats follow Chestnut remains an open question.
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