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A Preview of the 2022 Elections in Wisconsin (Part III: Mayor of Milwaukee)
Milwaukee's moving target of a mayoral election is going to be its most competitive in a generation. The field is beginning to get settled.
This is Part III of our series taking a look ahead from one year out at the 2022 election landscape in Wisconsin. Part I focuses on the big picture and the race for U.S. Senate and Part II is on state races for governor, attorney general and lieutenant governor. Be sure to read those first before you dive into Part III on the race for Mayor of Milwaukee.
As someone writing from the city of Milwaukee, this might be the most interesting race of all in 2022. And unless Bobby Portis decides to run — he’d be a lock, of course — it’s going to be a closely contested race.
This special election to finish out Tom Barrett’s term, which runs until 2024, will be the first truly competitive mayoral election many of us in this city have ever experienced. The last close race was when Barrett was elected in 2004, defeating Marvin Pratt 54% to 46%. The next closest race of the five elections in Barrett’s tenure was in spring 2020, when he defeated State Sen. Lena Taylor by 26%.
But before we talk about the actual race, we have to talk about timing. Because timing will be key.
If Barrett is confirmed as the U.S. Ambassador to Luxembourg (still a weird thing to see all written out, not gonna lie) before Dec. 28, the Common Council would call a special election that would coincide with the Spring Election. If that were to happen, a primary would be scheduled for Feb. 15, with a general election on April 5.
With that outcome, we’d be less than three months away from a primary right now as we sit here today. That would really light up the Milwaukee political world. Those campaigns would really have to hustle (in the dead of winter, mind you).
If Barrett’s confirmation occurs after Dec. 28 — and given how things are going in the Senate with Ted Cruz using “largely unprecedented” maneuvers in the Senate Foreign Relations Committee to hold up hundreds of the Biden administration’s nominees, that’s certainly a very possible outcome — the timing of the special election becomes a moving target.
According to Wisconsin Public Radio, if Barrett is confirmed between Feb. 15 and March 2, the mayoral primary would coincide with the April 5 Spring Election, with the general election set for May 3. If he is confirmed between April 16 and May 9, things shift to the fall election cycle, with the primary held on Aug. 9 and the general election on Nov. 8.
There are cost issues involved with all of this — an estimated $350,000 for a standalone election — but what really is the best time for Milwaukee to cast their votes in this race? What would best serve this city? Would a quick process be best to give the people a say in who will be mayor until the term ends in 2024? Would it make the most sense to have this coincide with the general election in the fall (and would that help boost turnout in Milwaukee for the midterms)? Would an April primary/May general be the best compromise between the two so that it’s neither rushed nor dragged out?
Part of this is up to Barrett. Nothing in his initial Senate hearing signaled any significant opposition to his nomination, so it would be a surprise if he were not confirmed. He could choose to resign at whatever time best served the city he’s led for the better part of two decades. But what is that best time? The city needs to answer that question, too.
As for the campaign, so far, those entering the race include Council President Cavalier Johnson (who will become Acting Mayor when Barrett resigns), Alderwoman Marina Dimitrijevic, Milwaukee County Sheriff Earnell Lucas, and former alderman Bob Donovan. Additional candidates that have filed, according to Urban Milwaukee, include Swarmm Events founder Michael Sampson, Nicholas McVey and Sheila Conway-Patterson.
State Rep. Daniel Riemer has not yet officially announced his candidacy, but he has confirmed to The Recombobulation Area that he is planning to run for mayor.
Alderman Khalif Rainey had been considering a run, but now he says it would be “highly unlikely” that he’d enter the race.
The timing of this special election could have an impact on who eventually enters the race. If the primary happens on Feb. 15, candidates with strong name recognition and campaign infrastructure will obviously have an advantage. In that case, the field could already be set. If it happens later in the year, a larger field could open up. Elected officials from the state legislature who might be impacted by redistricting, for example, could pivot and run for mayor. More candidates from outside of politics could give it a look. It’s not so often that this job opens up, after all.
One thing is for certain as this race gets moving: There is going to be a strong push for Milwaukee to elect its first Black mayor in this election. Marvin Pratt was Milwaukee’s first Black mayor when he became acting mayor after John Norquist resigned, and Johnson will be acting mayor when Barrett resigns, but this incredibly diverse majority-minority city that is now nearly 40% Black has never elected a Black mayor in its history. With Johnson and Lucas both running, you have two Black candidates with a real chance at making history.
If the field ends up being Johnson, Dimitrijevic, Donovan, Lucas, and Riemer, that makes for a pretty compelling group.
Of that group, Johnson would appear to be the early frontrunner. He checks a lot of the boxes that voters are going to be looking for in this election. He’s a smart, young, Black leader who would be able to push that reset button that Milwaukee needs to take a fresh look at the many issues the city is facing. He could, in many ways, follow a path like that of County Executive David Crowley (someone we’ve been fans of around here), who Johnson has worked closely with on key issues like local control.
Johnson is also going to have his opportunity to step in as acting mayor and be in the top job by the time this election is held. Coming from a position of quasi-incumbency could undoubtedly help, but in this city, there’s always a chance that a crisis could arise, and when that happens, people tend to point fingers at leadership.
And while the Council President and District 2 Alderman could be an early favorite, he’s certainly not a distant favorite. This is not going to be the kind of race where someone runs away with it.
For one, there will be a lane for a candidate to run to the left of Johnson on a number of issues. That could be Dimitrijevic’s path. It wouldn’t be a surprise to see some of the city’s more progressive organizations back her candidacy, and as the former County Board Chairwoman and current Chair of the Public Safety and Health Committee, she’s a well-known and established name in Milwaukee.
She could also make history in this race as the first woman elected as mayor of Milwaukee. That, too, would be a big, big deal.
Bob Donovan could make a real impact on this race, but there’s a hard ceiling on how far he’d be able to go. Many insiders think he could emerge from the primary, running on a law-and-order, tough-on-crime type of platform. But there is absolutely no chance that he wins a general election in the city of Milwaukee. None. When he challenged Barrett in 2016, he didn’t even manage to get 30% of the vote. If Donovan becomes one of the two candidates on the ballot in the general election, his opponent is all but guaranteed to win.
I think it’s unlikely that he emerges from the primary. Milwaukee likes a winner, and if people know he can’t ultimately win, that’s going to cloud their ability to support him. And with Lucas on the ballot, people who might be inclined to vote for a tough-on-crime candidate could cast their vote for an actual sheriff instead of Donovan.
Sheriff Lucas won a county-wide race when he was victorious in a competitive primary in 2018. Taking over post-David Clarke, he’s brought some much-needed stability and competence to that office. But he’s in his first term, and turning things around from where they were is no small lift. He also does not have the same level of political experience as many of the other candidates in this race. Then again, that could work to his advantage for people looking for more of an outsider. Prior to his role as sheriff, he was Major League Baseball’s Supervisor of Security for Commissioner Bud Selig. It’s going to be interesting to see how conversations about his candidacy play out. His might be the toughest to predict.
Riemer looms as a particularly intriguing addition to this race for when his candidacy officially begins. He’d be coming from the State Assembly, where he’s currently in his fifth term, so he’s experienced, but hasn’t been in the mix for city or county politics the way some others in the field have (which has its advantages and disadvantages, of course). He’s willing to take bold stances on big issues, like how he’s been especially critical of Gov. Tony Evers on the proposed expansion of I-94 that would slice through his district. If he’s able to establish a clear base (no small task), he could make some noise in this race.
However this all plays out, there’s one thing you can be sure of: You will be able to find bold, progressive coverage of each of the big elections happening in 2022 here at The Recombobulation Area.
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ONE LAST THING: As supporters of local journalism and (presumably) fans of the Milwaukee Bucks, I wanted to share with you a quick word about an important new effort: Several Milwaukee journalists have created a new scholarship to honor longtime Journal Sentinel reporter and storyteller Meg Jones, who passed away last year. I didn’t get a chance to know Meg, but she was always someone that people thought the world of. She was a terrific writer and covered a wide variety of topics and issues across Wisconsin, specializing in military and veterans affairs, traveling overseas to Iraq and Afghanistan eight times. The partners in this fund have set a goal of raising $50,000 to create a scholarship for University of Wisconsin-Madison journalism students.
Meg was also a huge Wisconsin sports fan, so the scholarship committee is organizing an online auction featuring all sorts of terrific sports memorabilia from the local teams, including a basketball signed by NBA Champion Khris Middleton (!). Other items include baseballs signed by Josh Hader and Brandon Woodruff, a football signed by LeRoy Butler, framed iconic photos and front pages, and more. The bidding will take place at www.facebook.com/megjonesfund, and you can find out more about the effort at megjonesfund.org or in the video below. I encourage you to support the Meg Jones Scholarship Fund!
Dan Shafer is a journalist from Milwaukee who writes and publishes the award-winning column, The Recombobulation Area. He previously worked at Seattle Magazine, Seattle Business Magazine, the Milwaukee Business Journal, Milwaukee Magazine, and BizTimes Milwaukee. He’s also written for The Daily Beast, WisPolitics, and Milwaukee Record. He’s on Twitter at @DanRShafer.
Follow Dan Shafer on Twitter at @DanRShafer.