Chicago will make history Tuesday, as voters choose between Toni Preckwinkle or Lori Lightfoot, the last two candidates standing after the free-for-all touched off by Mayor Rahm Emanuel’s announcement he would not run for a third term.

With an African American woman certain to win only the fourth open-seat contest for mayor in the last century, Chicago is entering a new epoch — one full of challenges that promises to put an end to business as usual at City Hall.

Here’s what the The Daily Line team will be watching as results roll in after the polls close at 7 p.m.

Were the polls in the mayoral race accurate?

Since the first round of voting, public polls have told a consistent story: Lightfoot is set to cruise to a convincing victory over Preckwinkle and become Chicago’s first gay mayor.

That prompted the Tribune’s editorial page to encourage voters to turn out for Lightfoot by a convincing margin to give Lightfoot a mandate to make good on her promises to fumigate City Hall, even as a federal corruption investigation continues behind the scenes.

Related: Dump aldermanic prerogative, clerk, treasurer, infrastructure trust: Lightfoot

If Preckwinkle does lose on Tuesday, she won’t be out of a job. Instead, she’ll keep her  position as Cook County Board president and the chair of the Cook County Democratc Party — potentially forcing the two former rivals to work together for much of the next four years.

The Rev. Jesse Jackson may have had that outcome in mind when he pressed the two to agree to a post-election unity event — which will no doubt be tense after the deeply negative and bruising runoff campaign in which Preckwinkle cast Lightfoot as a wealthy corporate lawyer and Lightfoot painted her rival as a compromised product of the Chicago political machine.

Whomever wins will face a city budget swimming in red ink — thanks to the city’s massive pension debt — and new contracts to negotiate with teachers, police officers and firefighters.

What will the mayor’s relationship look like with the new City Council?

Although Chicago’s City Council was designed to wield the lion’s share of power at City Hall, it has served as a rubber stamp for decades — first under former Mayors Richard J. Daley and Richard M. Daley and then under Emanuel, who has given his aldermanic allies several hundred thousand dollars in an attempt to shape the city’s political future after his departure.

Related: Aldermanic alliances mapped

Regardless of whether Preckwinkle or Lightfoot emerges victorious Tuesday night, the new mayor will have to quickly figure out the new political landscape at City Hall — and prepare to figure out how to push her agenda through.

Both Lightfoot and Preckwinkle have said they will not pick committee chairmen but will work with the council to suss out new leadership. The two part on other ethics reforms — Lightfoot has said she will work to end aldermanic prerogative, which she blames for fostering the culture of corruption that has convicted 30 aldermen of corruption since 1973, ban aldermen from holding outside employment, and enforce term limits.

Preckwinkle, a former alderman, has leaned toward keeping the system much the same.

The next mayor will also have to cope with a police department under a consent decree to reform, as well as an activist community — nearly all of whom who endorsed Preckwinkle over Lightfoot, the former head of the Chicago Police Board — demanding rapid change.

Treasurer’s race: Conyears-Ervin v. Pawar

In the runoff for treasurer, Ameya Pawar, who served two terms as 47th Ward alderman, faces state Rep. Melissa Conyears-Ervin.

Pawar’s proposal to create a public bank has dominated much of the conversation around the race. Under his proposal, the bank would be limited to “refinancing student loans, funding affordable housing and banking cannabis.”

By contrast, Conyears-Ervin’s campaign has focused on a message of “accountability, transparency and efficiency” while highlighting the support of the Chicago Teachers Union, the Chicago Federation of Labor as well as Secretary of State Jesse White, U.S. Rep. Danny Davis and more than two dozen aldermen.

Conyears-Ervin is married to 28th Ward Ald. Jason Ervin, who won re-election in April. He is the vice chairman of City Council’s Budget and Government Operations committee.

If Pawar wins, he would be the first Asian American elected to citywide office — and the first non-African American since 1999, when former Treasurer Miriam Santos resigned in disgrace as part of a corruption scandal. If Conyears-Ervin wins, Chicago will have three women of color serving in citywide office. Clerk Anna Valencia's bid for a full term was uncontested in February.

Pawar’s decision to leave the City Council after two terms set the stage for a runoff between Michael Negron, who has the support of his former bosses Emanuel and Massachusetts Sen. Elizabeth Warren, who tweeted her support Monday, and Matt Martin, an attorney in the Illinois Attorney General’s office who has the backing of the Chicago Teachers Union.

Political dynasties in flux

As the Laurino era ends jn the 39th Ward — where Ald. Margaret Laurino (39) will retire and be replaced by Samantha Nugent or Robert Murphy — a new dynasty may take root in the 30th Ward.

Jessica Washington Gutiérrez is challenging Ald. Ariel Reboyras, a close ally of Emanuel.

Gutiérrez, the daughter of former U.S. Rep. Luis Gutiérrez, has promised to be a more progressive alderman would be one of a number of millenials that could be elected to the City Council on Tuesday.

In the 33rd Ward, Ald. Deb Mell — who replaced her father, former Ald. Dick Mell — is facing Rossanna Rodríguez-Sánchez, who could be one of five members of the Chicago chapter of the Democratic Socialists of America to join Ald. Carlos Ramirez-Rosa (35) on the City Council.

Veteran aldermen, Emanuel allies at risk

In addition to Reboyras, who as chairman of the Public Safety Committee helped shepherd the mayor’s police reforms through the City Council after the dashcam video of Laquan McDonald’s murder roiled the city, several of Emanuel’s other allies faced tough run offs.

In the 40th Ward, Ald. Pat O’Connor faces a runoff against DSA-endorsed Andre Vasquez — the first since he was elected to the City Council in 1983. O’Connor has benefitted from more than $225,000 in spending by Super PACs aligned with Emanuel, charter school backers and Realtors.

Super PACs formed by charter school backers, Realtors, Rahm’s allies spending big bucks in last days of campaign

Other Emanuel allies at risk are:

 

• 5th Ward Ald. Leslie Hairston, who faces activist Will Calloway


• 6th Ward Ald. Roderick Sawyer, who faces accountant Deborah Foster Bonner


• 15th Ward Ald. Raymond Lopez, who faces Chicago Police Officer Rafael Yañez


• 21st Ward Ald. Howard Brookins, who faces retired city inspector Marvin McNeil


• 43rd Ward Ald. Michele Smith, who faces former Emanuel aide Derek Lindblom


• 46th Ward Ald. James Cappleman, who faces scientist Marianne Lalonde

 

20th, 25th Wards set for new aldermen after corruption allegations

Two wards at the center of corruption allegations will get new aldermen.

In the 20th Ward, DSA-endorsed Jeanette Taylor faces Nicole Johnson to take the seat left vacant in March when former Ald. Willie Cochran pled guilty to wire fraud after he was indicted for extortion and bribery.

In the 25th Ward, DSA-endorsed Byron Sigcho-Lopez faces nurse Alex Acevedo, whose father is former state Rep. Eddie Acevedo.

Progressive aldermen in 16th, 31st Wards face challenges

In the 16th Ward, Ald. Toni Foulkes faces Democratic Committeeperson Stephanie Coleman, the daughter of former Ald. Shirley Coleman.

In the 31st Ward, Ald. Milly Santiago faces Felix Cardona, a former aide to former Assessor Joe Berrios. In 2015, Santiago defeated longtime Berros’ ally Ald. Ray Suarez by 79 votes.

Veterans exit

Chicago City Council lost 132 years of combined experience in retirements and defeats in the first round — 155 years if you count 23rd Ward Ald. Mike Zalewski's early exit and replacement by Ald. Silvana Tabares.

Aside from younger members like Ald. John Arena (45), Ald. Proco Joe Moreno (1), Ald. Ameya Pawar (47) and Ald. Willie Cochran (20), more senior members like Ald. Margaret Laurino (39), Ald. Danny Solis (25), Ald. Joe Moore (49), and Ald. Ricardo Muñoz (22) are also exiting.

City Council has several senior members still standing. Aside from a weakened Ald. Ed Burke (14), first elected in 1969, Black Caucus members Ald. Carrie Austin (34), first elected in 1994, Ald. Walter Burnett Jr. (27), first elected in 1995, Ald. Anthony Beale (9), first elected in 1999, and Ald. Emma Mitts (37), first elected in 2000, have the most seniority. Other senior members Ald. Pat O’Connor (40), first elected in 1983, and Ald, Leslie Hairston (5), first elected in 1999, are facing stiff challenges.

Essential reads as Chicago votes

Issues facing the next administration:

• Is Chicago’s legacy of segregation causing a reverse Great Migration? [Reader]


• Why Chicago Police Reform Could Hinge On This Expired Contract [WBEZ]


• Emanuel Soft on Chicago Polluters Despite Tough Talk [BGA]


• Diagnosing Chicago’s affordable housing shortage [The Daily Line]


• Chicago police solve one in every 20 shootings. Here are some reasons why that’s so low. [Tribune]


• My house is worth how much? Fixes to tax assessments bring dramatic changes for Chicago homeowners [Tribune]


• Chicago spent more than $113 million on police misconduct lawsuits in 2018 [Reporter]


• With CPS poised to release 2018-19 enrollment data, ‘astronomical’ decline expected to continue [The Daily Line]

Where Lightfoot and Preckwinkle differ:

• Lori Lightfoot And Toni Preckwinkle Want An Elected School Board — But The Similarities End There [WBEZ]


• The Candidates Agree on Most Issues. Rent Control Isn't One of Them [Chicago Mag]


• Side-by-side: Lori Lightfoot’s and Toni Preckwinkle’s plans for Chicago [Sun-Times]


• How mayoral candidates Lori Lightfoot and Toni Preckwinkle have ducked details on Chicago's financial woes [Tribune]


• Preckwinkle, Lightfoot Talk Consent Decree, Policing Reform at Campus Forum [Maroon]


• Where do Lori and Toni part ways on transportation issues? [Reader]


• In Tribune meeting, Lori Lightfoot and Toni Preckwinkle clash over power of aldermen, City Hall corruption [Tribune]

City Council:

• Veterans day or heavyweight prize fight? Longevity vs. change in ward races [Sun-Times]


• Runoff to the Finish [South Side Weekly]


• Super PACs formed by charter school backers, Realtors, Rahm’s allies spending big bucks in last days of campaign [The Daily Line]


• Unions contributed more than $9.7M to candidates since August: records [The Daily Line]


• Sawyer vows to make his case to voters after being forced into runoff by challenger [The Daily Line]


• As Laurino era ends, Murphy, Nugent vie for 39th Ward seat on the City Council [The Daily Line]


• Jeanette Taylor, Nicole Johnson Set To Advance To April 2 Runoff In 20th Ward Race To Replace Cochran [Block Club Chicago]


• 25th Ward Candidates Trade Jabs On Campaign Donations, Voter Fraud Investigation At Heated Pilsen Debate [Block Club Chicago]


• More money no problems [Reader]


• In Fight For 40th Ward Seat, Ald. Pat O’Connor And Andre Vasquez Trade Barbs Over Each Other’s Past [Block Club Chicago]


• In Lakeview, Cappleman And Lalonde Make Their Case To Condo Dwellers, Showing Divide In Policy — And The 46th Ward [Block Club Chicago]


• Hundreds Flock To Davis Theater To Hear 47th Ward Candidates Debate Affordable Housing, Taxes [Block Club Chicago]