Ald. Pat O’Connor’s long tenure could put him in danger in city’s ‘safest’ ward

After considering retirement but deciding he wasn’t ready, Ald. Pat O’Connor (40th) is trying to extend his rein as the longest-tenured North Side alderman, facing four challengers who say his 36 years on the job are more than enough.

O’Connor, 64, trails only embattled 14th Ward Ald. Edward Burke on the Chicago City Council’s seniority list and recently replaced Burke as chairman of the council’s influential finance committee.

But after eight years as Mayor Rahm Emanuel’s floor leader and two decades before that as a loyal soldier in Mayor Richard M. Daley’s council majority, incumbency is a double-edged sword for O’Connor.

His longevity lets him take credit for changes in the ward he says have made it the “safest place in the city of Chicago.”

But those changes have ushered in a new generation of residents, some who regard O’Connor as a relic of the Democratic machine, and challengers vying to emerge as a progressive alternative.

Among those seeking to force O’Connor into a runoff are Chicago Public Schools math and science teacher Dianne Daleiden, digital marketing entrepreneur Maggie O’Keefe, community activist Ugo Okere and Andre Vasquez, a manager for AT&T.

Judging solely by volume of applause, O’Connor’s supporters seemed to comprise a plurality of the crowd that earlier this month packed the auditorium of The Waldorf School at Foster and Ashland to hear the candidates.

But it takes a majority of votes to avoid a runoff, and on this night the challengers turned out enough combined support to suggest in this very unscientific sampling that they might deny O’Connor an outright win on Feb. 26.

In 2015, Daleiden made a respectable showing against O’Connor, losing by a margin of 58 percent to 42 percent in the first contested election for 40th Ward alderman this century.

At the Waldorf forum, she referred to that campaign in a nod to her fellow challengers that didn’t quite tag them as Johnny-come-latelys.

“Four years ago, I stood alone against the Machine,” Daleiden said. “It was interesting. Luckily, I have no fear. I’m very happy to see this complement of young people up here have joined us in the fight.”

Though new to aldermanic politics, each of the other challengers points to involvement in recent progressive political campaigns — Vasquez on behalf of Bernie Sanders, O’Keefe for new Cook County Assessor Fritz Kaegi and Okere in the effort to lift the state ban on rent control.

O’Keefe told the story of the first time she called O’Connor’s office for help with a problem involving a T-alley behind her new apartment that she considered a hazard and a nuisance because of excessive honking.

She said O’Connor’s staff told her it would take a long time to solve the problem through the city council and that she probably would move soon anyway because she was a renter. “So what I suggest to you,” she said she was told, “is that you stand outside in a clown costume with a sign that says, ‘Don’t honk!’”

The story drew knowing laughter from many in the audience but no reaction from O’Connor, who kept his head buried in paperwork on the table in front of him except when it was his turn to answer a question.

Vasquez went further than the others in calling out O’Connor, saying he was surprised that the Sun-Times and Chicago Tribune endorsed the alderman for re-election, adding, “But I’m guessing they like corruption headlines.”

Okere, a Nigerian immigrant who works in the Evanston city clerk’s office, said the 40th Ward needs a “healthy injection of democracy.” He is promising monthly town halls, community-driven zoning and participatory budgeting.

The 40th Ward wraps around Rosehill Cemetery, encompassing parts of Andersonville, Bowmanville, Budlong Woods, Ravenswood, West Ridge and West Edgewater.

O’Connor, who was first elected in 1983, pointed to work he has done to make the community safer, improve schools and help neighborhood organizations solve local problems.

“Our community has thrived, and it will continue to thrive under my leadership,” he said.

In nine terms on the council, O’Connor has displayed occasional wanderlust, running two losing campaigns for state’s attorney and one for Congress.

Now, if he can survive — and depending on what happens with Burke — he could end up as the dean of the council.

Or he might find out it would have been easier to just retire.