Bob Donovan was born and raised in the Jackson Park neighborhood of Milwaukee, Wisconsin, and graduated from Saint Thomas More High School.

During his college years, he had worked as a laborer during the summers at Milwaukee Solvay Coke & Gas Co., a coal processing plant.

[1] Milwaukee Solvay Coke went out of business in 1983 and Donovan worked a number of jobs in the years after, including security officer at Southridge Mall and later for a pest control company.

[1] Donovan first entered politics as a Republican candidate in 1982, challenging incumbent Democratic state representative Joseph Czarnezki in what was then the 17th Assembly district.

Donovan decided to challenge Frank for his seat on the city council, but his 1996 campaign failed to make the ballot due to invalid nomination forms.

[1] In the 2000 election, however, his opponent, G. Eddie Paez, brought up a previously unknown 1992 incident when Donovan was arrested and fined for peeping through a hole in a partition between two stalls in a men's room on the UWM campus.

[1] As alderman, Donovan took the unusual step of opening up a district office, funded by local businesses and staffed by volunteers.

He also founded a nonprofit, the Milwaukee Alliance, which launched the south side's community prosecution unit to address neighborhood issues like absentee landlords or nuisance properties.

[1] Donovan stepped down from Milwaukee Alliance after the United States Attorney, Steven M. Biskupic, began looking into federal funding he had secured for the nonprofit.

[1] Ultimately, Donovan was indicted for fraud and making false statements to the United States Department of Housing and Urban Development.

The deal also prohibited Donovan from any involvement in federally-funded groups for the next two years, and required him to cut all ties with the Milwaukee Alliance.

He stood out in a crowded primary field as the only conservative candidate, and again ran on an anti-crime platform, calling for more police and tougher penalties for criminals.

[14] He faced Democrat Lu Ann Bird in the general election, a former Whitnall School District board member from Hales Corners, Wisconsin.