Kathy Osterman was an ace recruiter of celebrities, persuading politicians, movie stars, and other notables to mingle with the elderly residents of Lawrence House, an Uptown senior citizen residence, where she worked as Social Director before winning election as 48th Ward Alderman. In the early days of the Jane Byrne administration, before the city’s chief executive returned to the dark side (from where she had originated), Police Commissioner Joseph DiLeonardi visited with residents and Osterman told him of the problems Alderman Marion Volini was having with the local police commander, who wo ..read more

Citizens Information Service of Illinois (CIS), a non-partisan group that provided organizational skills training to community-based organizations, held a “Celebrity Waiters Lunch” as a fund-raiser and elected officials waited on tables and brought food and drinks to guests. When Alderman Dick Mell joked about how he was doing something new and different, City Treasurer Cecil Partee said that he had done this for real when he was younger because he needed a way to earn a living ..read more

Helen Shiller was the most progressive Alderman in the Chicago City Council during her six terms (1987-2011) representing the 46th ward, often advocating policies to help people who were struggling to survive in underserved communities. But she also had to serve more affluent constituents. In one case, she negotiated with the Chicago Park District to allow some Lake Shore Drive residents to park overnight in Lincoln Park, since they had no parking facilities in their buildings, and there was a shortage of parking spaces on city streets ..read more

Parents of some Morgan Park High School students were angry when the Chicago Board of Education changed attendance boundaries and required their kids attend Carver High School, which served the Altgeld Gardens CHA development. It wasn’t about race – the student bodies at both schools were mostly Black. The Morgan Park parents lived in a middle-class community and didn’t want their kids going to school in “the projects ..read more

When the Chicago Park District held its budget hearings, a CPD speaker said how proud they were that the District’s budget document had won an award for how well it was compiled. But constituents didn’t care about how the document was crafted. They cared about what was included in, and excluded from, the budget ..read more

A couple of people who didn’t like politics at all couldn’t stop gushing about a candidate they met who had been working the spectator area at a Fourth of July parade. “He was just wonderful!” one of them said with great enthusiasm. The candidate was Barack Obama and he was running for U.S. Senator at the time. I knew about him but I was still surprised these people would have reacted the way they did. I thought that Obama guy must have a whole lot of charisma ..read more

When 50th Ward Alderman Jack Sperling was notified of his appointment as a Circuit Court Judge in 1973, he shared the information with soon-to-be Aldermanic candidate Ray Cohen before the announcement was publicized. He wanted to give his ally time to get his affairs in order, raise money, and be positioned to launch a campaign before his potential opponents even knew a special election was going to be scheduled to fill Sperling’s unexpired Aldermanic term ..read more

When former State Rep. Michael Holewinski ran for 45th ward Alderman in 1979, Democratic precinct captains told voters that he had voted with other “baby killers” in support of abortion, despite having voted “present” on abortion bills while serving in the Legislature. But the Machine thought that would be an effective way to make many Catholic voters – who were the overwhelming majority in the ward – not want to vote for him. And it did ..read more

When Illinois elected three state representatives from each legislative district, the Democratic and Republican parties only slated two candidates in each district, thus allowing each party to hold at least one seat in every district in the state. Occasionally, the dominant party in the district sought to exert its strength and tried to corral all three seats. In addition to the two party-slated candidates, it fielded one person who ran on the Independent line on the ballot and outpolled the competitor of the smaller party. That’s how Taylor Pouncey was elected to three of his terms in an Engl ..read more

43rd Ward Democratic Committeeman Daniel O’Brien campaigned for three different U.S. Senate candidates in the 1984 primary election. He was running for re-election to his party post and wanted to be allied with the right candidate in each part of his ward. So, in the lakefront high-rises he supported Paul Simon. In the Black precincts he supported Roland Burris. And in the working-class precincts he supported the party-slated candidate, Phil Rock. Simon carried the ward and O’Brien was re-elected ..read more