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FNN Perspective: Cynthia Moore Chestnut’s Byron Donalds Endorsement Spotlights Nearly Four Decades of Public Service and Cross-Party Politics
Gainesville Democrat’s support for the Republican nominee renews debate over Black representation, party loyalty, political choice and the freedom to disagree
FNN PERSPECTIVE — Gainesville City Commissioner Cynthia Moore Chestnut’s endorsement of Republican gubernatorial nominee Byron Donalds has generated criticism from fellow Democrats and opened a broader discussion about party loyalty, Black political representation and an American political tradition that allows voters and public figures to cross party lines for many different reasons.
This perspective examines Chestnut’s decision in the context of her nearly four decades of public service, her stated reasons for supporting Donalds, historical examples of cross-party endorsements and the freedom of Americans to support — and criticize — political candidates.
Cynthia Moore Chestnut’s Nearly Four Decades of Public Service
Chestnut’s endorsement represents one decision in a public-service career extending back nearly four decades.
A Tallahassee native, Chestnut earned a bachelor’s degree in speech pathology from Florida A&M University, a master’s degree in speech pathology from Florida State University and a doctorate in public administration from Nova Southeastern University.
She became the first Black woman elected to the Gainesville City Commission, then broke additional barriers in state and county government. She became the first woman and first Black person elected to represent Florida House District 23 and later the first Black woman elected to the Alachua County Commission and the first to chair it, according to her official city biography.
Chestnut also became deeply involved in Democratic Party leadership, including service in county and state party organizations.
That history helps explain why her decision to support a Republican for governor has attracted attention beyond an ordinary political endorsement.
Why Cynthia Moore Chestnut Endorsed Byron Donalds
Chestnut has made clear that she remains a Democrat.
She initially emphasized political independence, her belief that Black voters should not be considered the property of either party and her desire to see Florida elect its first Black governor.
But Chestnut has since provided additional context.
In a Sept. 5 interview, she said Democratic nominee David Jolly’s selection of Gwen Graham as his running mate significantly influenced her decision. Chestnut criticized what she called an “all-white ticket” and said she believed Jolly missed an opportunity to select a Black or Hispanic running mate who could broaden the ticket’s representation and appeal.
Chestnut also said she spoke with Donalds and came away impressed that he listened to her. She told the interviewer that supporting Donalds does not mean she is becoming a Republican and said she does not support President Donald Trump.
Those additional details are important because they demonstrate that Chestnut’s endorsement cannot accurately be reduced to a single consideration.
LaVon Bracy Davis Strongly Disagrees With Chestnut
Democratic state Sen. LaVon Bracy Davis has offered a sharply different assessment.
Bracy Davis criticized the endorsement and questioned how Chestnut could reconcile her history of Democratic and Black political leadership with Donalds’ political record.
Her objections have included Donalds’ positions on voting rights and his relationship with the MAGA movement. Bracy Davis also rejected the idea that the possibility of electing Florida’s first Black governor should outweigh her concerns about Donalds’ policies.
The disagreement illustrates an important feature of political expression: Chestnut is free to explain why she crossed party lines, while Bracy Davis and others are equally free to challenge the reasoning behind that decision.
Cross-Party Endorsements Happen for Many Different Reasons
There is no single explanation for crossing party lines.
Voters and political leaders may support someone from another party because of policy, qualifications, leadership, personal relationships, representation, dissatisfaction with their own party, a particular issue or their individual assessment of the candidates in a particular election.
American political history contains numerous examples.
Some Democrats have supported Republicans. Some Republicans have supported Democrats. Others have left one party entirely or changed their registration.
Those decisions should be examined individually rather than treated as politically equivalent.
Gen. Colin Powell and Other Republicans Crossed Party Lines for Barack Obama
One prominent example occurred during the historic 2008 presidential election.
Republican former Secretary of State and retired Gen. Colin Powell endorsed Democratic nominee Barack Obama over Republican nominee John McCain, despite Powell’s longstanding friendship with McCain.
Powell cited several considerations, including leadership, economic issues, foreign policy, the direction of the Republican campaign and McCain’s selection of Sarah Palin. He described Obama as a “transformational figure” and said that although he recognized the racial significance of the election, race was not the dominant reason for his endorsement.
Powell was not alone.
Obama’s campaign organized a Republicans for Obama effort that included former Republican Rep. Jim Leach of Iowa, former Republican Sen. Lincoln Chafee of Rhode Island and former Bush foreign-policy adviser Rita Hauser. Republican Fairbanks Mayor Jim Whitaker also endorsed Obama.
Leach cited foreign policy and the national interest in explaining his decision. The various Republicans who supported Obama therefore did not necessarily cross party lines for precisely the same reason.
Obama went on to become the first Black president of the United States.
Obama and Donalds Are Different — The Comparison Is Cross-Party Choice
The historical comparison should have clear limits.
Barack Obama and Byron Donalds are different candidates, from different political eras, with different records, constituencies and policy positions. Likewise, Powell’s reasons for endorsing Obama were his own and should not be equated with Chestnut’s reasons for endorsing Donalds.
The relevant historical connection is narrower: prominent political figures have crossed party lines for different reasons throughout American political history.
Powell made one decision based on his assessment of the 2008 candidates. Chestnut has made another based on her stated considerations in Florida’s 2026 governor’s race.
Neither example establishes how someone else should vote.
John McCain Demonstrated That Opposition Does Not Require Misinformation
The 2008 campaign provides another relevant lesson — this time about political disagreement rather than endorsement.
McCain was trying to defeat Obama.
Yet during an October 2008 campaign event, McCain corrected supporters who expressed fear about Obama and rejected a woman’s false characterization of Obama as an Arab.
McCain described Obama as a “decent family man” and citizen with whom he had serious disagreements on fundamental issues. He also urged his supporters to remain respectful.
McCain did not stop opposing Obama. He continued campaigning against him.
The episode demonstrated that vigorous political opposition and respect for factual accuracy do not have to be mutually exclusive.
Political Expression Includes Endorsement and Criticism
That principle brings the discussion back to Chestnut.
Political speech and association receive substantial protection from government infringement under the First Amendment, subject to established legal limitations.
Americans can advocate for candidates, criticize public officials, associate politically, change parties or decline to follow a party’s preferred candidate.
But freedom of expression does not insulate a political decision from criticism.
Chestnut can explain why she believes Donalds deserves her support. Bracy Davis and others can argue that Donalds’ record should disqualify him from receiving that support.
Political freedom does not require everyone to reach the same conclusion.
David Jolly’s Political Journey Adds Another Dimension
The 2026 governor’s race itself demonstrates that political affiliations can change.
Democratic nominee David Jolly previously represented Florida in Congress as a Republican. He subsequently left the Republican Party, became unaffiliated and registered as a Democrat in 2025 before seeking the Democratic nomination for governor.
His situation is different from Chestnut’s.
Jolly changed parties. Chestnut says she remains a Democrat while supporting the Republican nominee.
But the two circumstances reinforce a broader point: party affiliation can be important without determining every political decision an individual makes.
One Endorsement, Nearly Four Decades of Public Service
Chestnut’s Donalds endorsement may become one of the most debated decisions of her long political career.
Critics can consider it significant. They can examine Donalds’ record, Chestnut’s stated reasons and her history in Democratic politics and reach their own conclusions.
Her broader record is also part of the story.
For nearly four decades, Chestnut has served in municipal, state and county government, broken racial and gender barriers, participated in Democratic Party leadership and remained active in Gainesville and Alachua County civic life.
One endorsement does not require the public to disregard that history. And nearly four decades of public service do not place one endorsement beyond public scrutiny.
Both can be examined together.
Florida Voters Will Make Their Own Choice
Ultimately, an endorsement does not cast anyone else’s ballot.
Chestnut has made her choice and explained her reasons. Her critics have exercised their freedom to challenge that choice. Donalds and Jolly will make their cases to voters.
Floridians will make the final decision for themselves.
That may be the larger lesson of the controversy surrounding Chestnut.
Cross-party endorsements happen for different reasons. Political affiliations can change. People who share a party affiliation can reach very different conclusions about candidates.
The ability to support, oppose, endorse, criticize, organize and vote reflects political freedoms that generations of Americans fought to expand — including Black Americans who confronted Jim Crow disenfranchisement and discrimination in the struggle for full political participation.
Chestnut’s nearly four decades of public service form part of that broader history.
Her endorsement of Donalds is now another chapter — one Floridians remain free to support, oppose, question or debate.
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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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