History Is on Hold in Milwaukee Mayor’s Race

A crowded and diverse field lines up to replace Barrett, but no one is sure how long U.S. Senate politics will keep their campaigns waiting.

The next election for Milwaukee mayor could both make history and be defined by history, yet it faces an uncertain future.

With seven candidates officially in the race and at least one more all but certain to enter, the field to replace Mayor Tom Barrett is already crowded and diverse. It could produce the city’s first elected Black mayor or the first woman to hold the office. At the same time, those groundbreaking candidates and their rivals come from backgrounds much like those of many who have sought the mayor’s job before.

Among the candidates are four well-known political figures: Common Council President Cavalier “Chevy” Johnson, Milwaukee County Sheriff Earnell Lucas, Ald. Marina Dimitrijevic and former Ald. Bob Donovan. State Rep. Daniel Riemer (D-Milwaukee) also says he’s planning to run, although he has not yet registered his campaign with the city Election Commission.

Still more could enter, drawn to only the fourth mayoral contest in 62 years without an incumbent on the ballot. Barrett emerged from a 10-candidate field in 2004, while his predecessor, John Norquist, defeated six opponents in 1988, and former Mayor Henry Maier won a six-way race in 1960.

But this time, the candidates face an unprecedented obstacle: They don’t know when the election will be. It might be this spring, at the same time as County Board and judicial races. It might be just a bit later, with a primary coinciding with the regular April general election and a standalone special general election in May. Or it might come in the fall, at the same time as the elections for Wisconsin governor, U.S. senator and other state and federal offices.

That all depends on exactly when the Senate confirms President Joe Biden’s nomination of Barrett as ambassador to Luxembourg. Republican senators, led by Ted Cruz of Texas and Josh Hawley of Missouri, are holding up dozens of State Department nominees over their differences with Biden administration national security policy. With Congress focused on Biden’s massive social safety net legislation, Senate Democrats may not break the logjam by the Dec. 28 deadline to add a mayoral race to the February primary ballot.

However, according to one theory being discussed in Milwaukee political circles, Republicans might not be the only ones interested in slow-walking Barrett’s confirmation. This theory holds that Senate Democrats may want to delay a vote past March 2 — just long enough to push the special mayoral election into the fall. Their goal would be to build up turnout in reliably blue Milwaukee for the midterm contests, when the winner of GOP Sen. Ron Johnson’s seat could decide control of their chamber, now evenly split.

“I believe that strategy is brilliant,” says public relations executive Craig Peterson, a Republican activist. “It’s sheer genius.”

State Sen. Chris Larson (D-Milwaukee) says he isn’t so sure, based partly on his difficulty stirring up interest in his 2016 and 2020 county executive campaigns, in contests that coincided with Wisconsin presidential primaries.

But perhaps unlike the county exec, “People understand what the mayor does,” says Angela Lang, executive director of Black Leaders Organizing for Communities. “It could definitely energize and boost Milwaukee turnout.”

Energizing and boosting turnout in the Black community is the specialty of Lang’s progressive organization, and she says this election could be the historic moment for the city to elect its first mayor of color. She notes that young people of color already hold three other major local posts: County Exec David Crowley, County Board Chair Marcelia Nicholson and Cavalier Johnson.

Johnson and Lucas are the major Black candidates in the race so far. BLOC helped Lucas win the 2018 sheriff’s race, but the group plans to thoroughly study the field before endorsing a mayoral candidate, Lang says.

Lang, Johnson and Lucas say they’re not worried about whether two strong Black candidates could split the Black vote and prevent either of them from advancing from the primary to the general election.

“I think it’s actually healthy to have robust conversations and as many candidates as possible and as many Black candidates as possible,” Lang says. She, Lucas and Johnson all stress that the Black community is not monolithic.

Still, Milwaukee could face a choice between electing its first Black mayor and its first woman mayor. Among the 12 largest Midwestern cities, only Milwaukee and Indianapolis have elected exclusively white male mayors.

Earlier this fall, Michelle Wu made history as the first woman and first person of color elected mayor of Boston, but many in that city’s Black community were disappointed that all three Black candidates were eliminated in the primary

Dimitrijevic says she followed the Boston race and was inspired by Wu’s example.

“It’s a ballot of firsts,” Dimitrijevic says of the Milwaukee field. “I’m thrilled to be here with other history-makers.”

Even as they’re poised to make history, the candidates also reflect historical patterns. Here’s how they stack up:

Council president:

In a race with no elected incumbent, Johnson will be the next best thing. As council president, he will be acting mayor from the time Barrett resigns to the time the special election results become official. That gives him an edge that other alders traditionally don’t have.

The last alder to win the mayor’s race was another council president, John Bohn, who took over after Mayor Carl Zeidler resigned in 1942 to serve in the Merchant Marine during World War II. Bohn won a full term of his own in 1944.

More recently, Marvin Pratt was council president when he became acting mayor after Norquist resigned in late 2003. Pratt ran for a full term the following spring, finishing first in the primary but losing to Barrett in the general election.

If people want an African-American mayor, “I’m African-American and I will be mayor,” Johnson says. But that approach didn’t work for Pratt, whose campaign slogan, “It’s time,” spoke to the hopes of Milwaukee’s Black community.

And unlike Pratt and other Black council presidents, Johnson won his office last year on an 8-7 vote with every other Black alder voting against him. Johnson says the council’s internal politics don’t reflect the sentiments of the wider Black community, an assessment shared by Peterson and Mordecai Lee, a professor emeritus at UW-Milwaukee.

Johnson was first elected to the council in 2016, after serving as an aide to Barrett. He says his combination of executive and legislative branch experience make him the most qualified candidate.

But Johnson’s association with Barrett also could be a negative for Black voters who feel the incumbent hasn’t done enough for them, Lang says. “Is he too close to Barrett?” she asks. “Is he going to be Barrett 2.0?”

Johnson’s most recent predecessors, Aldermen Ashanti Hamilton and Michael Murphy, have pondered running for mayor in the past but aren’t in the running now. Hamilton says he’s not considering it and Murphy says he’s “unlikely” to run.

Sheriff:

Milwaukee County has had three Black sheriffs, and all of them have run for mayor. For Lucas, the goal would be to finish better than predecessors Richard Artison, who lost to Norquist in the 1996 general election, or David Clarke Jr., who was eliminated in the 2004 primary (along with another Black lawman, former Police Chief Arthur Jones).

Lucas was a veteran Milwaukee police officer who survived a gunshot wound and rose to captain before joining Major League Baseball and becoming the national organization’s director of security. In the decisive 2018 Democratic primary, progressives rallied behind him to defeat Acting Sheriff Richard Schmidt, who had been second-in-command to the right-wing Clarke.

Like Johnson and Crowley, Lucas emphasizes his roots, growing up poor in Milwaukee and overcoming the barriers faced by many of the city’s Black residents. He says his history of leadership in both the public and private sectors sets him apart from other candidates.

But all of Lucas’ experience has been in law enforcement and private security, and that may not sit well with Black voters at a time of nationwide tension around high-profile incidents of sometimes-fatal police brutality against Black suspects, Lang says.

Alder:

Excluding council president Bohn, the last rank-and-file alderman to be elected mayor was also the first Socialist in that office: Emil Seidel, who won what was then a two-year term in 1910. That gives Dimitrijevic more than a century of history to overcome, in addition to the glass ceiling she hopes to break.

But Dimitrijevic has made history before, in 2004, when she became the youngest woman ever elected to the County Board. She served as a supervisor for 16 years, including three as board chair, before being elected to the council in 2020.

Dimitrijevic also served as executive director of the progressive Wisconsin Working Families Party. If elected, she could be Milwaukee’s most progressive mayor since Frank Zeidler, the city’s last Socialist leader,  left office in 1960. She says she admires Zeidler’s record of good government and infrastructure improvements.

A common explanation why alders so rarely rise to mayor is that they focus on neighborhood issues and command small political bases (unlike in Seidel’s day, when they were elected citywide). Lang notes that all of Dimitrijevic’s experience in office has been representing Bay View. Dimitrijevic counters that she has championed broad policy issues and advocated for the Hispanic community, including her Uruguayan-born husband.

Another council member, Ald. Khalif Rainey, told WISN-TV (Channel 12) he was considering joining the race, but later told The Recombobulation Area that he was “highly unlikely” to run.

Conservative:

In a city with a long history of Democratic and Socialist leadership, conservative candidates don’t gain much traction in mayoral races. Businessman George Watts garnered 44% of the vote in his 2000 challenge to Norquist, topping the 36% for firefighters union leader Greg Gracz, who took on Norquist in 1992.

Barrett rolled over Donovan, 70% to 30%, in 2016. But even before that race, Donovan had citywide visibility as an outspoken law-and-order advocate. Peterson and Lee say his name recognition and political base could make him a significant factor in the primary, even if he has little chance of success in the general election.

Donovan says his 20 years on the council, ending in 2020, gives him the most local government experience of any candidate.

Although he was a lifelong Milwaukee resident, Donovan has come under fire for recently moving to Greenfield. He says he and his wife, Kathy, are temporarily living in his late mother’s condo to open their South Side home to his son Eric’s family, while Eric faces health and financial challenges. Donovan says he and his wife will return to their house later this year, after his son moves to Illinois for medical treatment.

Legislator:

All of the last three mayors served in the state Senate, and two of the last three county executives (Crowley and former Gov. Scott Walker) were Assembly members.

Riemer says his service in the Legislature would give him an outsider’s perspective in a field dominated by local government insiders. He has represented a southwest side district since 2012.

His father, David, was a city and state administrator who lost to Walker in the 2004 county executive’s race.

And in a polarized body led by Republicans, Riemer says he has been able to work across the aisle. He’s part of a bipartisan group of cosponsors on a bill to authorize ranked-choice voting in congressional elections.

Among other legislators, Larson says it’s too early to say if he might enter the race. Two other Milwaukee Democratic state lawmakers who were considering it, Sen. Lena Taylor and Rep. David Bowen, have jumped into the contest for lieutenant governor. Taylor lost to Barrett in 2020 and to Walker in 2008.

Other officials:

Controversy surrounds City Attorney Tearman Spencer. Since his 2020 election, he’s been accused of sexual harassment and creating a toxic work environment that has driven staff lawyers out the door. Some of them question his competence. He feuds with the council and the news media. Some alders have even discussed removing him from office.

None of that would seem to be a foundation for a mayoral race, but the Journal Sentinel says Spencer is discussing the prospect. He has enjoyed strong support from U.S. Rep. Gwen Moore, a Milwaukee Democrat and longtime Black leader.

The last city attorney to win the mayor’s office was Daniel Hoan, a Socialist who was elected in 1916 and served 24 years, until he fell to Carl Zeidler, then an assistant city attorney, in 1940.

Presiding Municipal Judge Derek Mosley is pretty much the opposite of Spencer: well-liked and well-respected, with a fun side as a dining influencer and prolific wedding officiant. But while some see Mosley as a future mayor, state law prohibits him from holding any government office outside the judiciary until his term ends in 2023.

Also-rans:

Voters who have elected just seven mayors in 105 years clearly value experience. History isn’t on the side of mayoral candidates without a track record in elected or appointed office, whether they’re serious-minded academics like Ed McDonald, who lost to Barrett in 2012, or quirky attorneys like Andrew Shaw, crushed by Barrett in 2008.

That doesn’t bode well for the remaining registered candidates: event planner Michael Sampson, community activist Nick McVey and teacher Sheila Conley-Patterson. In a crowded field like this one, candidates like them usually are eliminated in the primary.

One possible exception would be an independently wealthy candidate like Chris Abele, who was willing to spend unheard-of sums to win and retain the county executive’s office. But Abele seems to have retired from politics.

Barring the emergence of another affluent outsider, the likelihood that the next mayor will be an experienced politician could be the most certain outcome in a race where very little is certain.

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Larry Sandler has been writing about Milwaukee-area news for more than 30 years. He covered City Hall and transportation for the Milwaukee Journal Sentinel, after reporting on county government, business and education for the former Milwaukee Sentinel. At the Journal Sentinel, he won a Milwaukee Press Club award for his investigation of airline security. He's been freelancing since late 2012, with a focus on local government, politics and transportation. His contributions to Milwaukee Magazine have included in-depth articles about our lively local politics, prized cultural assets and evolving transportation options. Larry grew up in Chicago and now lives in Glendale.