Last fall, a rally was held outside Fiserv Forum to welcome Damian Lillard, the newest Milwaukee Buck. The seven-time NBA All-Star was greeted by two prominent fans clad in Bucks gear: Milwaukee County Executive David Crowley and Milwaukee Mayor Cavalier Johnson. 

The 33-year-old Lillard was overheard expressing amazement: Milwaukee is run by two Black guys my age?  

Crowley and Johnson, both 37, made history by becoming the first African Americans elected to their respective positions, Crowley in 2020 and Johnson in 2022. 

In 178 years of Milwaukee mayors and 64 years of Milwaukee County executives, Black men had been appointed a few times to the jobs on a temporary basis. But only white men had been elected.  

Now, a new era has emerged in what remains a racially divided community.  

Polished politicians with legislative successes to tout, Johnson and Crowley appear set to easily win re-election in April. That would give them each four more years in their positions.  

Nothing in politics is certain. But barring scandal, it seems Johnson and Crowley can have their jobs for as long as they want – though running for higher office seems likely for both men. 

Regardless of how long they stay, the change away from electing only white men as mayor and county executive seems a lasting one. 

“This is a reflection of what’s happening in our community,” says Evan Zeppos, a consultant who has worked on local election campaigns for more than 30 years. “It isn’t a blip on the screen. It’s evolutionary, and I don’t think there’s any going back.”

JOHNSON AND CROWLEY’S poignant personal stories are well told eight years into their political careers, but still worth revisiting. 

Johnson (nicknamed Chevy) and Crowley grew up on Milwaukee’s North Side in ZIP code 53206, an area covering North Avenue to Capitol Drive on the north, and Interstate 43 to 27th Street on the west. Beset by high rates of poverty, poor health outcomes and vacant lots, 53206 is said to have the highest rate of incarceration of Black men in the U.S.  

Crowley’s parents used drugs; his family was repeatedly evicted from their homes. Johnson’s family also endured evictions; he attended six elementary schools. 

The two men reflected on their lives during a joint interview with Milwaukee Magazine in the Goddess Room of the Milwaukee County Executive’s Office. The room is named for a mural inside that depicts the Goddess of Fierce Protection, which was inspired in part by “modern-day history makers who represent strength in the face of negative forces.” 

Crowley was quick when asked if he thought he could grow up to become county executive:  

“Hell, no.”  

“When I was young,” says Johnson, “all you’re thinking about is trying to survive and get something better in life.”  

But there was a recognition that their fates weren’t sealed. 

“I remember sitting on the porch one summer” around age 9, Johnson says. “I just want more for my family, for myself, for my neighborhood. And I said, I’m going to pull my pants up and behave differently than what I see around here.” 

Programs such as the YMCA for Johnson and Urban Underground for Crowley provided structure and mentoring. “Fourteen-year-old me said I could be the first Black president!” Johnson recalls. 

Crowley and Johnson attended Bay View High School together, Crowley graduating in 2004 and Johnson a year later. Crowley didn’t earn a degree while attending UW-Milwaukee but is working toward one; Johnson earned a political science degree from UW-Madison in 2009. 

It wasn’t long before they each won their first elections. In 2016, Crowley was elected to the Wisconsin Assembly and Johnson to the Milwaukee Common Council. (Both are Democrats, but city and county offices are nonpartisan.) 

Crowley’s 2020 victory made him, at 33, the youngest-ever Milwaukee County executive. In 2021, Johnson, then Common Council president, became acting mayor when Mayor Tom Barrett resigned to become U.S. ambassador to Luxembourg. Johnson’s special election win in 2022 meant he would finish Barrett’s term. 

It was progress, but the community was still behind the times.  

When Johnson was elected mayor, the Journal Sentinel reported that of the 50 most populous U.S. cities, Milwaukee had the eighth-highest share of Black residents. Every other city in the top 10 had elected a Black mayor at least 10 years earlier.

THE KEY FORCES keeping white men in the top posts of local government all these years: culture, demographics, the power of incumbency and racism. 

“The city’s slow to change,” says Tarik Moody, 50, program director of Hyfin, an urban alternative radio station in Milwaukee and a member of the City Plan Commission. “That’s culture. I think that applies to politics.” 

Thad Nation, 51, leads a Milwaukee firm that guided Crowley and Johnson’s historic campaigns and is also leading their re-election runs. He notes that Black migration occurred later in Milwaukee than in other Midwestern cities. Political power, he says, tends to take three generations to build. “The first folks come and settle, the second folks establish the community and then the third generation starts to take over leadership,” he says. 

The repeated elections of white candidates as mayor and county executive not only made incumbents difficult to challenge, it affected the Black community’s psyche, says community organizer Angela Lang. 

“I think we’re obviously a strong voting bloc, but I don’t know if [Black] people always felt that they were the ones able to run for office,” says Lang, 34. She is executive director of Black Leaders Organizing for Communities, a Milwaukee-based organization that advocates for Black citizens, including getting them out to vote.  

“I’m a girl that grew up on 32nd and Wisconsin and thought politics was for white men who drank bourbon and smoked cigars and that’s how politics got done,” Lang says. “And, to a certain extent, it is how it gets done today. Some folks didn’t feel that we could actually be the ones to represent.”  

Greg Lewis, 66, executive director of Milwaukee-based Souls to the Polls Wisconsin, which works with faith leaders to get out the Black vote, agrees that Black Milwaukeeans underappreciate their political power. That is often reflected in low voter turnout.  

In the city in the 2020 presidential election, 65% of registered voters cast a ballot in majority-white wards, compared with 58% in majority-Black wards, according to John Johnson, a demographics and political trends researcher at Marquette Law School. In the 2022 midterm elections, the margin was 52% to 39%. 

Racism, in what has long been one of the most segregated metropolitan areas in the country, was another factor working against potential Black candidates, with lasting effects.  

On nearly all key measures of Black community well-being, Milwaukee ranked at or near the bottom among large metropolitan areas, says a 2020 UW-Milwaukee study that blames racism. 

“It is really prevalent here, but it is so sophisticated that it is almost subliminal,” Lewis says.

Racism and the Limits of Progress

“No, no, no, no. No,” says Tarik Moody, program director of Hyfin, an urban alternative radio station in Milwaukee and a member of the City Plan Commission. 

“We don’t have Jim Crow laws on the books, but they’re still in the head,” says the Rev. Greg Lewis, of Souls to the Polls Wisconsin. “I wouldn’t dare go for a long walk in Whitefish Bay at about 10 o’clock at night; I’ll find out what color I am if I do.” 

Angela Lang, of Black Leaders Organizing for Communities, says the two men’s elections alone don’t undo the effects of racism, but do create opportunities for change.  

“How we talk about the issues through a more inclusive lens is important,” she says. “I think we’ve seen that shift how people are thinking about the issues, but it’s going to take so much time to undo a lot of that harm.” 

Johnson and Crowley still witness racism.  

In fall, Johnson went to pick up an order from a suburban pizzeria because his wife mistakenly entered the wrong location online. Johnson recalls the conversation he had with an employee who recognized him. 

“Where’s your [security] detail? Aren’t you scared to be out at night by yourself because you’re coming from Milwaukee?” the employee asked. 

“No,” Johnson replied. 

“Well, you probably came here because you felt safe.” 

“That is the racism we experience on a daily basis,” Johnson says. “It’s not gone by a long shot.”

THE BREAKTHROUGHS MADE by Johnson and Crowley were due to their strength as candidates, but also a change in the complexion of the community. 

In 2000, four years before Barrett began his mayoral tenure, 54% of adults age 18 and over in the city were white; now it’s 39%, says John Johnson.  

Their victories, he says, “are a sign of the growing electoral influence of Black voters in Milwaukee and the increasing willingness of white residents to vote for Black chief executives.” 

(The proportion of Latino voters in both the city and the county is growing, but research shows Latinos are less likely to be citizens, less likely to register to vote and less likely to vote, according to John Johnson.) 

Johnson and Crowley seized relatively rare opportunities to run for open seats, an accomplishment that traditionally is much easier than defeating an incumbent. They also had big advantages coming into their election.  

Crowley was backed in the county executive’s race by multimillionaire Chris Abele, who had decided not to seek re-election as county executive. Abele led a group that spent nearly $200,000 on mailers and ads for Crowley during the final days of the campaign.  

The support was crucial in Crowley’s razor-thin 50% to 49.5% win over state Sen. Chris Larson. The Milwaukee Democrat, a white liberal, had lost to Abele in 2016. 

John Johnson’s analysis found that Crowley won by overwhelmingly carrying his political base on Milwaukee’s North and Northwest sides and by winning more conservative suburbs, including River Hills and Franklin.  

Johnson had a much easier time winning the mayoral election. By virtue of being the Common Council president, he became acting mayor four months before defeating conservative Bob Donovan, a white former South Side alderman making his second attempt at the mayor’s office. The margin was 72% to 28%. 

The torches had been passed. 

“This is a new generation of leadership from, not just anywhere in Milwaukee, but from some of the most challenged neighborhoods in Milwaukee,” Mayor Johnson says. “I think people saw value in that, saw value in our ability to bring the life experiences to our positions. 

“We were compelling enough and we were energetic enough and we had visions for the city and visions for the county that we were able to consolidate support across racial lines.” 

It was a marked contrast from a generation earlier. 

Unlike Marvin Pratt – whose 2004 campaign slogan for mayor was “It’s Time” – neither Johnson nor Crowley ran as a Black candidate, but as a candidate who happened to be Black, says Mordecai Lee, an emeritus political science professor at UW-Milwaukee.

Through the Years

1835: Milwaukee County is established. 

1846: City of Milwaukee is chartered. 

2004: Lee Holloway is chosen by his fellow county supervisors as the first Black chairman of the Milwaukee County Board of Supervisors. 

2004: Marvin Pratt becomes, in an acting capacity, Milwaukee’s first Black mayor. He serves for three months after John Norquist resigned, but Pratt loses his election bid. 

2010-11: Holloway serves two months as acting county executive after Scott Walker resigns. He gives up the post and runs for the office. Pratt serves two months as interim county executive until the special election to permanently replace Walker. Pratt does not run for the post, and Holloway loses. 

2020: David Crowley, a former state Assembly member, becomes the first Black elected Milwaukee County executive since the position was created in 1960. Cavalier Johnson, a Milwaukee alderman since 2016, is elected by fellow aldermen as Common Council president. 

2021: Johnson starts four months as acting mayor after Mayor Tom Barrett resigns to become the U.S. ambassador to Luxembourg. 

2022: Johnson becomes the first elected Black mayor, to serve the remainder of Barrett’s term. 

2024: The mayor and county executive posts are up for election; both are four-year terms. The primary is Feb. 20 and the spring election is April 2.

SCANDALS CAN THREATEN the career of any politician, Black or white. 

In 2020, Tearman Spencer won the city attorney’s job by defeating a 36-year white incumbent by 22 points, but his re-election is uncertain. With more than a year left in Spencer’s term, he drew a strong opponent in this April’s election in state Rep. Evan Goyke. The Milwaukee Democrat, who is white, decided to run amid a growing scandal that led the District Attorney’s Office last November to consider criminal misconduct charges against Spencer over allegations that he allowed a deputy to work at a private law firm while on the job.  

Johnson and Crowley have no such worries. 

This month, Johnson is facing two frequent also-ran candidates in a primary: Ieshuh Griffin and David King. Johnson is widely expected to prevail in the primary and general. Griffin is also challenging Crowley for the county executive seat in the April election. (A man named Daniel Crowley, no relation to David, threw his name in the hat for county executive but did not collect enough signatures to appear on the ballot and force a primary.) According to the latest campaign finance reports available at press time, filed in July, Johnson had $348,610 cash on hand and Crowley had $251,551.  

Observers perceive the pair as not overly partisan politicians who appear to be managing their government competently. There haven’t been enough shortcomings or failures to make a compelling argument to replace them. Meanwhile, they can point to policy victories earned together. 

Johnson and Crowley worked with the Republican-controlled Legislature to produce two key laws last year. One that gives more shared revenue to all municipalities statewide also enabled the city of Milwaukee to create a sales tax and Milwaukee County to increase its sales tax – allowing both entities to avoid bankruptcy. The other law aims to keep the Brewers in Milwaukee through 2050 by providing state, city of Milwaukee and Milwaukee County funds for improvements at American Family Field. 

Residents didn’t start feeling the sales taxes until January, so there’s still the potential for backlash. But in the meantime, Johnson and Crowley avoided presiding over what was framed during the debate of the legislation as the financial demise of the city or county. “Folks want for there to be people in these offices who are willing to dig in and get stuff done; they’re not looking for bomb throwers, they’re not looking for folks who are uber-liberal or uber-conservative,” Johnson says.  

Crowley says the successes show “a changing of the tide,” but he isn’t overconfident. “We have probably the largest magnifying glass on us,” he says. “Everyone is watching everything that we say.”

Rising Stars on “the Bench”

“There’s a bench of really impressive young leaders of color who are coming up in Milwaukee,” Johnson says. “So, in no way do I think I’m going to be the last mayor of color in Milwaukee.” Crowley interjects, laughing: “I better not be” the last county executive of color. 

Some of the younger Milwaukee leaders mentioned by Johnson: 

Marcelia Nicholson, Milwaukee County Board chair. Like Crowley and Johnson, she was born and raised in 53206. Elected chair by her fellow supervisors in 2020 and re-elected in 2022, she is the first Black woman and Latina to hold the post.  

Kalan Haywood II, member and assistant minority leader of the state Assembly. He was just 19 when he became the youngest state lawmaker in Wisconsin history upon his election in 2018. 

Dora Drake, state Assembly member elected in 2020. 

LaTonya Johnson, state senator and member of the Legislature since 2012. 

Lamont Westmoreland, Milwaukee alderman elected in 2023. 

JoCasta Zamarripa, Milwaukee alderwoman since 2020. In 2011, she was the first Latina elected to the Wisconsin Legislature.

The Bay View Pipeline: Mark Chambers Jr. went to Bay View High School with Crowley and Johnson; he’s in the aldermanic seat of Milwaukee’s 2nd District that Johnson held. Yet another Bay View High classmate of theirs, DiAndre Jackson, is a candidate for 7th District alderman.

SINCE 1960, when the county executive post was created, all but one of the six elected county executives before Crowley served at least eight years. Among elected mayors, Johnson’s predecessors served 17 years (Barrett), 16 years (John Norquist) and 28 years (Henry Maier).  

That pattern would suggest that Johnson and Crowley can expect to serve multiple terms. 

Retiring South Side Milwaukee Ald. Mark Borkowski, 65, a conservative who has been on the Common Council since 2015 and previously served on the County Board for 23 years, hopes that Johnson and Crowley spend some of their political capital to address problems such as reckless driving and other crime. 

“In my eyes, they do not use the bully pulpit the way they should,” Borkowski says. “They’re missing out on a great opportunity, because they have a lot of cachet and they have a lot of respect. But there’s a little bit of a risk when you start calling people out.” 

Borkowski noted that Johnson and Crowley attended a memorial Mass for reckless driving victims in November. “Fine, but what about the people that were driving those vehicles?” he says. “There’s no accountability. Call out these judges, call out the district attorney.” 

Nevertheless, Borkowski sees political longevity for both men: “You want to talk about dynasty? They’re not even 40 yet.” 

Synergy on efforts such as the sales tax and stadium laws help Johnson and Crowley politically. 

“There’s this broad sentiment that government is toxic, it’s dysfunctional, it can’t actually work, so sometimes people are relieved to see these two leaders actually work with each other,” says Lang. “I think they know that their partnership is strategic not only for their re-election, but how folks have confidence in how government is functioning.” 

But Nation notes there could be a downside to governing together: “It does hurt them because they often get confused for one another,” he says. “People don’t pay that close of attention.” 

With Johnson and Crowley seemingly safe in their positions, if they leave it’s likely to run for governor, the seat held by U.S. Rep. Gwen Moore or the U.S. Senate. 

Regardless, observers expect, at least for the foreseeable future, there won’t be a return to white-males-only for mayor and county executive. 

“I think people would demand consistent Black representation, or at least Black or brown to reflect diversity of the city,” says Lang. “I don’t know if people would have confidence in another mayor or county executive that was not Black or brown. It’s almost like once you cross that threshold, you can’t think of really going back.”