And that was hardly the end of the matter. In July, after Billy Ocasio resigned to go to work for Governor Pat Quinn, Mayor Daley announced that he was naming Maldonado the 26th Ward’s new alderman. This set off alarms with the residents of the 1700 block of North Monticello. Since aldermen generally have final say over land-use matters in their wards, Maldonado’s appointment meant that he was now the person he would have to go through to enact the zoning change he wanted. The residents began gearing up to fight the proposal when it came before the City Council’s zoning committee.

No other member of the council owns close to that much real estate, according to financial disclosure statements. One alderman, the 44th Ward’s Tom Tunney, owns 11 properties, though all but his home are units in two adjacent buildings he owns on Belmont. Four others (George Cardenas, Latasha Thomas, Walter Burnett, and Patrick O’Connor) own four, and six others (Michelle Harris, Ed Burke, Willie Cochran, Richard Mell, William Banks, and Joe Moore) own two. The remaining 38 aldermen don’t own any properties that they don’t live in.

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Maldonado acquired many of his holdings for modest sums after their previous owners stopped paying taxes. In several cases—such as with the Monticello and Central Park lots—he sat on them for years as their values soared. And in one instance he cut a land-swap deal with Bickerdike Redevelopment Corporation, which has received both accolades and intense criticism as one of the ward’s leading developers of affordable housing.

But others have not been so rigorous. There are numerous examples of council members who’ve been busted for taking bribes from developers in return for zoning changes, including Arenda Troutman, the former 20th Ward alderman who went to prison earlier this year. But the classic example of an alderman-developer gone wrong has to be Thomas Keane, a fierce ally of Mayor Richard J. Daley who chaired the council’s powerful finance committee from 1958 until 1974, when he was imprisoned for fraud.

As of August 18, the four lots on Monticello and Central Park were listed on local realty sites for $649,900 altogether. Maldonado’s property at 1733 N. Troy had a for sale by owner sign in front of it last week, and four lots he owns on the south and west sides were listed for $39,000 apiece.

In 1994, with Gutierrez’s backing, he was elected to the Cook County Board; he was reelected three times. As a commissioner he rarely bucked the lead of board president John Stroger or his successor and son, Todd.