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Ten Chicago City Council Races to Watch

Three aldermen with a combined 114 years of experience are in tight spots. That could mean a younger, more independent Council than ever.

Photography: Chicago Tribune, Facebook

The City Council is set for a big turnover in 2019, and its next class will likely be more independent, more Latino, more female, and a whole lot younger than the current one. The Council’s three most senior aldermen — Ed Burke, Pat O’Connor, and Joe Moore, with a combined 114 years in office — are all facing difficult challenges from fresh candidates.

The Progressive Caucus, which now numbers 12 aldermen, is also expecting to bolster its membership, which will mean a Council more likely to challenge the next mayor’s power. Here are ten races that will determine the makeup of that Council.

(Aren’t sure which ward you live in? Look it up here.)

The 5th Ward (Hyde Park, Woodlawn)

Hairston, Calloway.

Ald. Leslie Hairston angered activists when she refused to support their demands for a Community Benefits Agreement for the Obama Center, which would hold the Obama Foundation accountable for economic investment in Jackson Park.

One of her opponents is William Calloway, an activist who helped force the release of the Laquan McDonald shooting video. Calloway favors the Community Benefits Agreement, as well as a property tax freeze and rent control, which he says will protect residents against rising real estate prices the Center is expected to bring. Also running is former Hyde Park Herald Gabriel Piemonte.

The 14th Ward (Archer Heights, Brighton Park, Gage Park)

Burke, Guzmán, Patino.

This may be the last go-round for Ed Burke, the longest-serving alderman in Chicago history. As he seeks his 13th term, Burke is dogged by his past work securing real estate tax breaks for Donald Trump, a figure anathema to the Mexican-Americans who make up 80 percent of his ward.

Burke was also recently indicted by the FBI for allegedly shaking down a Burger King owner in his ward. Two of his challengers — Jaime Guzmán and Tanya Patino — have connections to Congressman-elect Chuy Garcia, who has been Burke’s sworn enemy ever since they were on opposite sides of Council Wars in the 1980s. (Garcia has endorsed Patino.)

The 20th Ward (Washington Park, Englewood)

Bailey, Taylor, Driver, Johnson

Ald. Willie Cochran is retiring, as he faces charges of soliciting, bribing, and embezzling from a charity he created. The favorite to succeed him is Ward Committeeman Kevin Bailey, who won 45 percent of the vote against Cochran in 2015.

Bailey, however, is facing a host of candidates with roots in South Side activism. Jeannette Taylor has been one of the most outspoken voices in favor of a CBA for the Obama Center. Anthony Driver devoted himself to gun violence after two of his friends were murdered. Nicole Johnson, a former school teacher who now works for the community organization Teamwork Englewood, was one of the young candidates interviewed in Chance the Rapper’s Chicagoist video on the duties of an alderman.

The 30th Ward (Avondale, Belmont Cragin)

Reboyras, Gutierrez

In the heavily Puerto Rican 30th Ward, there’s a battle between two Latino candidates — one establishment, one progressive. Incumbent Ariel Reboyras is an Emanuel ally who chairs the Public Safety Committee, which oversees the police department. He was prominent in the now-disgraced Hispanic Democratic Organization.

Reboyras’s challenger is Jessica Gutierrez, daughter of former U.S. Rep. Luis Gutierrez, who this year handed his congressional seat to Chuy Garcia.

Emanuel is endorsing Reboyras, who contends that their relationship has brought parks, playgrounds, and schools to the ward. Gutierrez is appealing to progressive followers of Garcia, who won 59 percent of the ward’s vote in the 2015 mayoral election.

The 33rd Ward (Albany Park, Irving Park, Avondale)

Mell, Rodriguez-Sanchez, Sieracki

The Mell dynasty is dying.

Former Gov. Rod Blagojevich, son-in-law of patriarch and former alderman Dick Mell, reported to prison in 2012. Then, in 2013, Mell retired and handed off his city council seat to his daughter Deb Mell. In 2015, he helped her avoid a runoff by 81 votes. But the elder Mell won’t be there to help his daughter this time around, having lost his committeeman’s seat in 2016.

Deb Mell’s strongest opponent in the Latino-majority 33rd Ward is Rossana Rodriguez-Sanchez, a self-described socialist whose anti-establishment campaign has been compared to that of U.S. Rep. Alexandria Ocasio-Cortez. Another progressive, Katie Sieracki, has the endorsement of mayoral candidate and former Police Board president Lori Lightfoot.

The 37th Ward (Humboldt Park, Austin)

Mitts, Stamps

Ald. Emma Mitts considered it a coup when Mayor Rahm Emanuel decided to build a $95 million police training academy in her West Side ward. But the project is unpopular among police reform activists, who say the money would be better spent on mental health and education.

Mitts is facing a rematch with schoolteacher Tara Stamps, who forced her into a runoff in 2015. Stamps has the endorsement of the Chicago Teachers Union.

The 40th Ward (Ravenswood, Budlong Woods, Bowmanville)

O’Connor, Daleiden, O’Keefe, Okere, Vasquez

Along with Burke, Ald. Patrick O’Connor is one of last remaining members of the Vrdolyak 29, which opposed Mayor Harold Washington during Council Wars. In his quest for a 10th term, O’Connor faces four opponents: Dianne Daleiden, Maggie O’Keefe, Ugo Okere, and Andre Vasquez.

During an October debate moderated by author Rick Perlstein, O’Connor accused the Nigerian-born Okere of circulating a fundraising letter that “doesn’t talk about community, it talks about building Nigerian power in Chicago.”

The next day, Perlstein went on social media and condemned O’Connor as “a racist troll.”

The 46th Ward (Uptown, Lake View)

Wozniak, Cappleman

Oriole Park Elementary teacher Erika Wozniak is challenging Ald. James Cappleman, who has been accused of treating homeless people like pigeons after rousting tent cities from the Wilson and Lawrence viaducts.

Wozniak has the backing of Congressman-elect Chuy Garcia. This race will be a test of whether Garcia’s appeal to progressives transcends the Latino community.

It will also test whether this is the same ward that voted six times for Helen Shiller, a fierce opponent of gentrification. Probably not, as Uptown now resembles Lincoln Park more than the funky enclave it was through the ‘90s.

The 47th Ward (Lincoln Square, Ravenswood, North Center)

Negron, Kitzes, Martin, Dordek

Everyone is running to replace Ald. Ameya Pawar, who is honoring his pledge to serve only two terms, and is instead campaigning for city treasurer. They’re all connected, and they’ve all got money. This is Mayor Rahm Emanuel’s ward, after all.

Among the favorites: Michael Negron, a Harvard Law grad and former aide to Barack Obama and Emanuel; Heather Kitzes, a lobbyist for the Cubs; Matt Martin, a civil rights attorney for the Illinois Attorney General’s office; and Eileen Dordek, a social worker involved in campaigns for women’s and LGBTQ rights.

Expect the candidates to spend $2 million, making this the city’s most expensive council race.

The 49th Ward (Rogers Park)

Moore, Hadden

Ald. Joe Moore was a thorn in Mayor Richard M. Daley’s side, proposing ordinances that were either vetoed or overturned (a foie gras ban, a requirement that big box retailers pay a living wage). But he’ss become a close ally of Emanuel, whose policies he insists have been more progressive than his predecessor — namely raising the minimum wage and closing power plants.

Rogers Park likes an independent alderman. Moore’s opponent, Maria Hadden, an activist who sits on the board of BYP100, promises to be just that. On the council since 1991, Moore has had a long and distinguished career, but a desire for generational change may tell against him.

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