Lessons from Chicago and Wiscosin

Two recent elections will have major consequences throughout the Midwest.

In Chicago, Cook County Commissioner Brandon Johnson defeated former Chicago Public Schools CEO Paul Vallas in a close and bitterly contested election, with Vallas conceding gracefully.

At least compared to the next loser.

Across the border in Wisconsin, Milwaukee District Judge Janet Protasiewicz decisively defeated former Wisconsin Supreme Court Justice Dan Kelly by a double-digit margin.

Dan Kelly was a sore loser.

The consequences are quite divergent as well.

Who occupies Chicago's mayor’s office has significant consequences for hundreds of thousands, if not millions, of people. But many of the structural problems that brought down former Chicago Mayor Lori Lightfoot (and after two terms, Rahm Emanuel) will face Mayor-elect Johnson in full force, just as they would have faced Vallas if he had won the race. Most likely, Johnson is going to get chewed up even if he manages to get some good things done as mayor of the Windy City.

Truth is, despite the economic and cultural wonder that Chicago is, I internally debate if I should congratulate him or send my condolences—which is the same debate I had regarding current Los Angeles Mayor Karen Bass when she won her race.

But the results of the Wisconsin State Supreme Court election are a fundamental game change for Badger State Democrats.

Results and Lessons from Wisconsin

For the first time, Democrats can do something about fixing the most gerrymandered maps in the country, securing reproductive rights, and repairing the immense damage done by former Wisconsin Governor Scott Walker.

I am happy to report that I was right about Democrats winning this race. But I underestimated the margin.

Democrats began to substantially breach the WOW counties, gaining substantial amounts of ground in Ozaukee County.

Republicans could have put up a far stronger candidate in Waukesha County in Judge Jennifer Dorow, a conservative ideologue who nonetheless has legitimate experience as a judge outside of politics and grassroots support in the vital WOW counties. But instead, they put up Dan Kelly, a candidate who lost by double digits as an incumbent in the 2020 Wisconsin Supreme Court election and provided legal counsel to those looking to overturn the 2020 results in Wisconsin. Not to mention he has made it quite clear in the past he would enforce Wisconsin’s 1849 abortion ban without mercy and was closely tied to Donald Trump.

Dobbs, denial, and Donald.

On the other hand, Democrats put up Judge Janet Protasiewicz, a judge based out of Milwaukee with solid experience as a prosecutor and a judge. Someone who made it clear she would protect reproductive rights in the Badger State and had plenty of solid connections in Wisconsin’s legal world.

Candidate quality mattered immensely in this race.

As did investment and campaign operations.

In both of these fields, the Wisconsin Democratic Party has demonstrated it has come a long way since the dark days of Scott Walker. It outspent and outworked its Republican counterparts by a comfortable margin, and Democrats nearly won a Republican State Senate seat that was having a special election, located North of Milwaukee.

In the future, this does not mean the Republican Party of Wisconsin is still not a formidable opponent. This is the same party that was able to nearly win Wisconsin for Donald Trump even as he ran the country into the ground with his incompetence.

The Wisconsin Democratic Party has merely improved its game by leaps and bounds.

Key lessons here include investing in a good ground game and making sure your state party’s operations are solid, lessons clearly learned and carried out by Wisconsin State Party Chair Ben Wikler—one of, if not the, best chairs of a state Democratic party in the country.

Money and candidate quality matter immensely.

Last but not least is the impact of the Dobbs decision.

Idaho recently passed a state law targeting women seeking reproductive health care in other states. Under the regime of Governor DeSantis, Florida signed a bill to ban abortion after six weeks.

The Dobbs decision is proving that Republicans don’t care about how many women get killed in the name of being pro-life.

Women across the country are acutely aware their rights are largely dependent on what state they live in. In Wisconsin, this fact was no less salient.

Every election going forward is going to have abortion on the ballot in some capacity.

This election also demonstrates how vital it is to have credibility with your constituents.

Which segues nicely into the mayoral election in the Windy City.

Results and Lessons from Chicago

Before we get started, I will lay my biases on the table.

I disliked both Brandon Johnson and Paul Vallas. Johnson, because he helped put a knife in Lightfoot even after she gave the Chicago Teachers Union everything it wanted after a strike. He is also unacceptably close with Bernie World for comfort. I disliked Vallas because he is way too chummy with the Chicago Police Union, he palled around way too much with the far right, and he disrespected Presidents Obama and Biden. On policy, I have serious problems with both candidates, and I don’t think it’s healthy that the choices facing Chicago voters came down to someone on the far left and a Democrat who is excessively acquainted with the far right.

I consider both candidates Democrats, just Democrats I don’t like very much.

I am usually good with Democratic candidates getting support from chambers of commerce or business groups in general because their interests are often the same as city interests, even where there are (frequent) points of sharp disagreement. Police unions, on the other hand, I deem unacceptable to rely on support from, and the fact the Chicago Fraternal Order of Police endorsed Vallas played a fundamental role in why Vallas made my skin crawl.

With all of that said, I regarded Brandon Johnson the lesser of two evils, but I was expecting Paul Vallas to win based on the results of the first round of voting, turnout patterns before the last day of voting, money, and endorsements.

Clearly, I got Chicago wrong.

One of three things happened.

Paul Vallas and his allies dropped the ball and botched an easily winnable election, Brandon Johnson ran a far better campaign than I thought he did during the election, or a combination of both.

What objectively happened is that the people who voted for Lightfoot, mainly Black voters on Chicago’s South Side, got Johnson over the finish line, along with a significant number of Latino voters on Chicago’s West Side, thanks in large part to Representative Chuy García’s endorsement. In addition, it appears that Vallas underperformed in vital areas across Chicago’s borders, Downtown Chicago, and much of Chicago’s North Side compared to how Johnson overperformed on the West and Southside—underperformance that was serious enough to allow Johnson’s surge in support among Lightfoot’s voters to garner him the win.

Personally, I think it was a combination of Johnson running a better campaign than I thought along with Vallas making grave, serious mistakes.

But right now, if I had to say which was the larger factor, I would say Vallas’s bad decisions played the more significant role, if only by a margin.

He had all the advantages going into the general election. He had almost twice as many votes banked, significantly more money, and more establishment backing from the Chicago political machine. Crime and other quality-of-life issues dominated, issues Vallas should have had little trouble exploiting (and in fact centered his campaign around), even with Chicago’s largely Black South Side.

But he still could not win the election with all of these advantages. I would say his serious weakness with Black voters (he failed to win a single ward on Chicago’s South Side or even come in third place in said wards during the first round of voting) along with his hobnobbing with the far right was what allowed enough breathing room for Johnson to make up the difference from having to gain at minimum two votes for every one vote Vallas needed, which his aggressive campaigning on the South and West Sides allowed him to pull off.

I am confident that if Lightfoot ran against Johnson, the former mayor would have easily won. Keep in mind she defeated a similar candidate in a landslide in 2019.

I would argue the biggest lesson out of Chicago is that it takes a (perceived) authentic Democratic candidate to defeat the far left in major cities, along with the obvious fact that it is practically required to have the support of Black voters (and other voters of color) as a Democrat running in the Midwest.

Look at what happened in Los Angeles with their mayoral election. It came down to then Representative Karen Bass and real estate mogul Rick Caruso. Caruso had a long history of donating to Republicans before becoming an independent in 2017. He registered as a Democrat right before running for office.

Karen Bass defeated Rick Caruso despite many of the top issues facing the people of Los Angeles being crime and skyrocketing rates of homelessness, issues that typically favor the more (relatively) conservative candidate. In this race, I would have gone with Bass because she has experience dealing with extreme crises. Recall that she was Speaker of the California Assembly during the worst days of the 2008 economic crisis and helped to forge a deal with then California Governor Arnold Schwarzenegger that left no one happy but saved California from economic collapse.

I will add the caveat that Bass is progressive but not far left, something like Vice President Harris.

In both Chicago and Los Angeles, voters who were upset with things like homelessness and crime nonetheless did not trust a relatively recent Republican or someone who had been keeping company with the far right to fix these problems.

Tough-on-crime and/or otherwise moderate Democrats can and often do get elected at the local level. Look at what happened when Chesa Boudin was recalled in early 2022 and how current San Francisco District Attorney Brooke Jenkins easily won reelection in the 2022 midterms. Or consider how then Brooklyn Borough President Eric Adams won the New York City mayor’s office in 2021. Adams built his political base on working-class Black and Hispanic New Yorkers, while Jenkins was pushed forward in large part by Asian Americans in San Francisco who were tired of being victimized by hate crimes. In Minneapolis, Mayor Frey expanded his margin of victory by growing his support on the largely Black Northside, with the clarification that he did quite poorly in other communities of color in Central Minneapolis, where George Floyd was murdered.

But you must have community credibility for the above strategies to work, even if it’s based on the other candidate being much worse.

The biggest lesson is that it is extremely difficult, if not impossible, to win as a Democrat without the support of Black voters, especially in the Midwest and South. Ask yourself: What did Bass, Johnson, and Adams all have?

Also, what enabled then Vice President Biden to come back from the dead several times when his campaign should have died in 2020?

Stay frosty, everyone.

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