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He first ran for office in this district-which was designed in order to maximize the political clout of the largely West Indian constituency that lies within this area, i.e. Flatlands, Flatbush, East Flatbush, and Midwood - in 1997 against then incumbent City Councilman Lloyd Henry. Although defeated in that race, Stewart went on to successfully contest the seat four years later in a crowded Democratic primary field, which included two other Caribbean-American candidates, and future State Senator Kevin Parker.
As the incumbent from that district, Stewart would face a tough re-election battle in 2005 when Samuel Taitt, who has become a perennial political rival for Stewart, decided to run against him for the seat yet again. One of the issues raised over the course of the campaign was a comment Stewart made that his opponents, as well as many Haitian-Americans, viewed as being derogatory towards Haitians. In response to an article published in the New York Daily News, which accused him of being a delinquent landlord, he asserted that the poor condition of his rental properties were the result of the behavior of Haitian-Americans. He also accused them of breaking locks, which he described as a "cultural thing". During Taitt's rematch against Stewart in 2005 Taitt insinuated that Stewart's campaign might have been behind defamatory campaign pamphlets circulated within the district one week prior to Election Day, a charge that Stewart's campaign vehemently denied.
Stewart has also been Democratic District Leader for the 58th Assembly District.
Stewart was defeated in the September 2009 Democratic primary by more than 1,100 votes by a newcomer, Jumaane Williams, but ran in the November 2009 general election on the Independence Party line. Nonetheless, he was defeated by Williams on election day, November 3, 2009.
- New York Times report on Kendall Stewart
- Stewart-Taitt accusations
- Taitt's accusations in 2005 against Stewart
- 2009 primary defeat
|New York City Council, 45th District