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Cynthia Chestnut
Cynthia Moore Chestnut.jpg
Member of the Florida House of Representatives
from the 23rd district
In office
November 6, 1990 – November 7, 2000
Preceded by Sidney Martin
Succeeded by Ed Jennings
Mayor of Gainesville, Florida
In office
1989–1990
Preceded by David Coffey
Succeeded by Courtland A. Collier
City Commissioner from
Gainesville, Florida
In office
1987–1989
Assumed office
February 2022
Constituency At-Large, Seat B
Personal details
Born Tallahassee, Florida
Political party Democratic
Residence Gainesville, Florida
Alma mater Florida A&M University (B.S.)
Florida State University (M.S.)
Nova Southeastern University (D.P.A.)
Occupation Politician

Cynthia Moore Chestnut is an American politician from the Democratic Party. She is currently serving on the Gainesville City Commission. She also served on the same City Commission from 1987 to 1989. From 1990 to 2000, she was a member of the Florida House of Representatives. She represented the 23rd District during that time. After running for the Florida Senate in 2000, Chestnut was elected to the Alachua County Commission in 2002. She served there until 2010.

Early Life and Public Service

Cynthia Chestnut was born in Tallahassee. She went to Florida A&M University and earned her bachelor's degree in speech pathology in 1970. She then attended Florida State University and received her master's degree in speech pathology in 1971. Later, she earned a doctorate in public administration from Nova Southeastern University in 1981.

In 1987, Chestnut made history. She became the first black woman elected to the Gainesville City Commission. Two years later, in 1989, the commission chose her to be Mayor. This made her the first black woman to serve as Mayor of Gainesville.

As of 2025, she is a Commissioner for the City of Gainesville. She also holds the role of Mayor Pro Tempore.

Serving in the Florida House of Representatives

In 1990, State Representative Sid Martin decided not to run for re-election. Cynthia Chestnut decided to run for his seat in the 23rd District. This district included parts of Alachua County and Putnam County.

First Election to the House

Chestnut faced two other candidates in the Democratic primary election. She won the most votes, but not a majority. This meant a second election, called a runoff, was held. In the runoff, Chestnut won against her opponent. She received 57% of the votes.

In the main election, Chestnut ran against Republican Sinclair Eaton. She talked about her experience on the City Commission. She also highlighted her support for public education. Chestnut won the election with 59% of the votes. She won by a large amount in Alachua County.

Later Terms and Key Work

In 1992, the district boundaries changed. Even with the changes, Chestnut was re-elected without anyone running against her. During her second term, she led the House Education Committee. She used this position to make sure Florida schools taught African-American history. She also made sure students learned about the Holocaust.

She continued to win re-election easily in 1994, 1996, and 1998. In 1998, she won her fifth and final term in the House without any opposition.

Running for State Senate

In 2000, State Senator George Kirkpatrick could not run again due to term limits. Cynthia Chestnut decided to run for his seat in the 5th District. This district covered many counties in Florida.

She ran against State Attorney Rod Smith in the Democratic primary. Chestnut focused her campaign on improving education. She wanted to review Florida's entire education system. Smith, however, was very popular in the district. He was well-known for his successful work as a prosecutor in important cases. Chestnut lost to Smith, winning 38% of the votes.

Serving on the Alachua County Commission

In 2002, Chestnut decided to run for public office again. She challenged Robert Hutchinson for his seat on the Alachua County Commission. She talked about her experience in government. She also focused on reducing poverty and improving the county's budget.

Chestnut won the Democratic primary election. She then faced a Republican and a Libertarian candidate in the general election. She won her first term on the County Commission with 58% of the votes. This made her the first black woman elected to the Alachua County Commission. In 2006, she was re-elected by an even larger margin.

In 2004, Chestnut was found to have broken a rule about accepting gifts. She had taken free tickets to an event.

In 2010, Chestnut ran for a third term. She lost this election to Republican Susan Baird. This was a big surprise, as Alachua County usually votes for Democrats.

Recent Public Life

Cynthia Chestnut
Official portrait, c. 2022

In 2012, Cynthia Chestnut's stepson, Chuck Chestnut, was elected to the Alachua County Commission. He had also served in the state House.

In 2014, Cynthia Chestnut was chosen to lead the Alachua County Democratic Party. She also ran for the position of Florida Democratic Party chair in 2021.

On January 25, 2022, Chestnut was elected to the Gainesville City Commission again. She won a special election after a close runoff. On February 17, 2022, she was sworn into the same office she had held over 30 years before. One of her first goals was to explore bringing a new multi-use complex to East Gainesville.

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