Alderman
A few months after his unsuccessful bid for re-election as State Representative, Bauer filed to run for a position on the St. Louis Board of Aldermen. As with the State Representative seat, the district included both the Hill neighborhood and the Dogtown neighborhood. The long-time incumbent from the Hill neighborhood was not seeking re-election. Two candidates from the Hill filed in the Democratic primary. Bauer was the only candidate from Dogtown. He again won the primary with less than 50% of the vote and won the general election in April 1999.
Shortly after his election as Alderman, Bauer had the opportunity to participate in the redistricting of Aldermanic ward boundaries required after the 2000 Census. The redistricting resulted in the Hill neighborhood being drawn into a new ward, with Bauer's ward consisting mostly of Dogtown.
In 2001 Bauer made a run for Comptroller one of the many city-wide elected positions in St. Louis. He challenged the incumbent, Darlene Green, an African-American woman. As with many political campaigns in St. Louis, the voting broke down along racial lines. Bauer carried most of the predominantly white wards in South St. Louis, while Green won the election based on strong support in predominantly black North St. Louis and in the racially integrated neighborhoods in the central part of the city.
In 2003, Bauer was re-elected as alderman of the re-districted ward, winning 59% of the vote in the Democratic primary and 71% of the vote in the general election . Although he had been elected to office three times, this marked the first time that Bauer had won a majority of the vote in a primary election. Bauer's pet donkey, Scotty, continued to be a fixture in his campaigns. Scotty had died by the time of the 2003 campaign, and had been replaced by a new donkey, named Dan. Although Dan accompanied Bauer on campaign stops, a drawing of a donkey labeled "Scotty" continued to be a fixture on Bauer's campaign signs and billboards.
As Alderman, Bauer was a proponent of efforts to bring residential and commercial redevelopment to the neighborhoods in his ward. The community he represented was traditionally working class, and the housing mostly consisted of modest bungalows. However, the neighborhood's central location and proximity to Forest Park began attracting more middle and upper class residents. Developers began demolishing some of the older single family homes and building attached luxury townhouses. Bauer consistently supported this type of development, although it generated some controversy.
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