Cynthia Moore Chestnut is an American Democratic politician who currently serves the Gainesville, Florida City Commission.

After unsuccessfully running for the Florida Senate in 2000, Chestnut was elected to the Alachua County Commission in 2002, where she served until she lost re-election in 2010.

Chestnut faced attorney Clay Phillips and insurance salesman Larry Harvey in the Democratic primary.

[5] Though Chestnut placed first the primary, winning 47% of the vote to Phillips's 41% and Harvey's 12%, because none of them received a majority,[6] a runoff election was held the next month.

[8] In the general election, Chestnut faced Republican nominee Sinclair Eaton, who had run for the seat previously in 1986 and 1988.

[11] Glass launched an aggressive, abusive campaign against Chestnut, calling her a "whore" who was "bought and paid for by the PACs" and advocating for the "violent overthrow of the government if things don't change.

[18] In 2002, Chestnut re-entered public life by announcing that she would challenge Alachua County Commissioner Robert Hutchinson, who represented District 4, in the Democratic primary.

Chestnut again focused on her support for reducing poverty and argued that public transportation needed to be more present and reliable in the poorer, eastern part of the county.

[25] In 2010, Chestnut ran for a third term on the County Commission and was opposed by Republican nominee Susan Baird, a Tea Party activist and a real estate broker.

[33] Among her initial areas of focus, Chestnut advocated for potentially bringing a new multi-use complex to East Gainesville.