How big policy wins put Cavalier Johnson and David Crowley in the political driver's seat

Milwaukee Mayor Cavalier Johnson (left) and County Executive David Crowley (right) are facing much different re-election challenges this spring compared to the multi-way races in which they won their first terms in recent years. This year also differs from the challenges faced by their predecessors.
Milwaukee Mayor Cavalier Johnson (left) and County Executive David Crowley (right) are facing much different re-election challenges this spring compared to the multi-way races in which they won their first terms in recent years. This year also differs from the challenges faced by their predecessors.
  • Oops!
    Something went wrong.
    Please try again later.
  • Oops!
    Something went wrong.
    Please try again later.

The upcoming elections for Milwaukee mayor and county executive barely resemble the races of just a few years ago.

Mayor Cavalier Johnson in 2022 and County Executive David Crowley in 2020 beat out multiple other candidates to win the seats they're looking to hold onto for a second term. Like many others in those elections, both Johnson and Crowley were already holding public office when they launched their bids.

Their predecessors, too, faced challenges from others in elected office.

But in a break from those recent elections, neither Johnson nor Crowley is facing a challenger with previous experience in office or with a comparable campaign war chest or public platform in this spring's elections.

Instead, voters on Tuesday will weigh in on the three-way mayoral race that has pitted Johnson against Wisconsin God Squad founder David King and Ieshuh Griffin, who is running under the slogan "The Poor People's Piece of the Pie Campaign."

Griffin, who is also on the ballot for a Common Council seat, is Crowley's lone challenger. That means there will not be a primary and the first time voters will go to the polls in the race for county executive is for the April 2 general election.

Crowley and Johnson attributed their lack of competition from within government to the relationships they've built and their accomplishments in their first terms, including securing local sales taxes that helped each of their governments avoid looming fiscal crises. On top of that is the city's agreement to host this summer's Republican National Convention that will put an international spotlight on the city and the Milwaukee Brewers stadium deal their administrations reached with the state.

Others noted their ability to communicate to the public their approaches to difficult issues their governments have faced and the lack of divisiveness that has characterized their tenures in office.

"It's hard to try to imagine what the opposition would be to them that would fund a candidate against them. ... There’s not an issue that they really fumbled or an issue that makes sense to challenge them on, so I think they’ve done a very good job of setting themselves up for re-election," said Patrick Guarasci, a consultant based in Milwaukee who was an adviser to former Mayor Tom Barrett’s campaign.

"I would not want to run a campaign against them," he added.

Mayor, county executive races have recently drawn contenders with name recognition, history in elected office

It's not uncommon in Milwaukee for elected officials who hold other offices to throw their hats in for mayor or county executive — whether or not there's an incumbent already in the race.

For Crowley and Johnson, winning a first term in office was not a foregone conclusion.

A half-dozen candidates sought the seats they currently hold, first when incumbent County Executive Chris Abele did not seek re-election in 2020 and less than two years later, when Barrett left office early to take a post as ambassador to Luxembourg.

Four years ago, Crowley was a state representative when he became one of six candidates who sought the open seat, four who made it onto the primary ballot, ultimately, and the winner of a close race against state Sen. Chris Larson.

Then in 2022, Johnson was acting mayor when he faced a similarly crowded field in the race for the final two years of Barrett's term. Unlike Crowley, though, Johnson beat former Ald. Bob Donovan by a much larger margin.

During their years in office, Barrett and Abele also faced challenges from opponents who were in the public eye. But even holding other public office was not enough to oust the incumbents in a city that re-elects the same people for long periods of time.

In his final race in 2020, Barrett faced a challenge from then-state Sen. Lena Taylor but won by a margin of 63% of the vote to Taylor's 37%. In recent weeks, Taylor was appointed by Gov. Tony Evers to the Milwaukee County Circuit Court bench.

Abele, in his final race in 2016, won by about 55% of the vote to Larson's 45%, according to figures from the county Election Commission.

The proven power of incumbency in Milwaukee coupled with Crowley's and Johnson's legislative accomplishments may be leading would-be challengers — and their would-be funders — to calculate that it's not worth taking on an expensive race to try to oust an incumbent.

Wins on local government funding, other legislation make for formidable incumbencies

Wins in their first terms have made Johnson and Crowley more formidable opponents for anyone who might be eyeing the seats they hold, multiple people told the Journal Sentinel.

"What elements are you going to criticize of their first term that would be dramatic enough to oust an incumbent?" said Theodore Lipscomb Sr., the former Milwaukee County Board chairman who was among Crowley's competitors in the 2020 primary.

On any of those issues, a challenger would have to offer a different course of action better than what's already underway and be willing to stake their success on it, he said.

Among the key wins many cited was the local government funding law through which the city and county gained additional revenue, including from long-sought local sales taxes, and averted financial crises.

Johnson and Crowley each recalled the disbelief they faced as they came into office talking about addressing the city's and county's financial challenges, given the long-strained relationship between past Milwaukee leaders and Republican lawmakers in Madison.

They were able to reach a deal, but the funding also came with a series of restrictions on its use and non-fiscal requirements specifically aimed at the city that angered some Milwaukeeans. Still, the strings attached to the funding weren't enough to prompt an electoral challenge.

"If they were considering a run for mayor, I think that they would look back into the electorate and know that the voters in Milwaukee are savvy, they're smart, and they know that it was important to save the city," Johnson said. "And they know that there were some political challenges to overcome or work through in order to do that."

Whether because of the broad recognition of the brokenness of Wisconsin's system for funding local governments or the dramatic local service cuts that loomed without additional funding or the broad support for the sales taxes including at the local level, the deal city and county leaders were able to strike with the state did not turn into a political liability would-be candidates could exploit.

Then, months later, came the $500 million state law to fund long-term renovations and improvements at American Family Field and keep the Milwaukee Brewers ballclub in Milwaukee through 2050. The funding plan requires $67.5 million each from the city and Milwaukee County to pay for work on the stadium over almost 30 years.

Gov. Tony Evers signs Assembly Bill 438 and Assembly Bill 439, a bipartisan package of bills passed by the Wisconsin State Legislature to keep the Milwaukee Brewers and Major League Baseball (MLB) in Wisconsin through 2050, on Tuesday December 5, 2023 at American Family Field in Milwaukee, Wis.
Gov. Tony Evers signs Assembly Bill 438 and Assembly Bill 439, a bipartisan package of bills passed by the Wisconsin State Legislature to keep the Milwaukee Brewers and Major League Baseball (MLB) in Wisconsin through 2050, on Tuesday December 5, 2023 at American Family Field in Milwaukee, Wis.

"Those are two major lifts that if you did either one of them in one term, it would be considered a massive success, let alone doing both of them in the span of less than a year with a Republican Legislature that doesn't have a history of doing nice things for Milwaukee," said Thad Nation, whose public strategies firm Nation Consulting is running both Johnson's and Crowley's re-election campaigns.

Johnson and Crowley may also be experiencing something of an extended honeymoon period in which would-be challengers are looking to see what the pair do with the greater financial stability and if federal pandemic aid allocations accomplish what was promised, said Ald. Marina Dimitrijevic, who was among the mayoral candidates in 2022.

She's also sensed a desire at City Hall for some continuity after significant turnover on the Common Council and in the Mayor's Office in just the last few years.

And, she noted, Johnson and Crowley also won historic elections, becoming the first African Americans to be elected to their seats.

"These are two younger, African American men who made history, so I think there's a lot of excitement and hopefulness surrounding those elections, too," she said.

And it's no coincidence that the high school friends have found shared successes on some of the biggest issues they faced.

"His success is my success and my success is his success — and I don't mean that personally, I just mean that from the city and county's perspective," Crowley said. "As the county executive, I want the City of Milwaukee to be strong and want them to be vibrant, because that contributes to our overall county, and quite frankly, our regional success."

Challengers to mayor, county executive have sought office before

For King, it came as a surprise that more people did not run against Johnson and Crowley.

He said he got in the race because he wanted "real leadership" and worried about issues like crime, homelessness, drug addiction and the quality of education in Milwaukee.

King said he thought his campaign would bring in more money after the primary but that it would rely on word of mouth and media opportunities, not spendy ads on television.

According to their latest campaign finance reports, Johnson and Crowley have $363,966 and $251,552 cash on hand, respectively.

By comparison, King had $476 cash on hand. For both her city and county races, Griffin filed as exempt as the money raised for her campaign falls below the required threshold.

King said people know him from his work in the city.

"I like it when I’m the underdog. He might outspend me in money, but he won't outwork me at all," King said of Johnson.

King unsuccessfully sought positions as Republican lieutenant governor in 2022, Milwaukee mayor in 2020, Milwaukee Common Council District 9 in 2016, and the U.S. House of Representatives in 2014, among others.

Griffin has long run in various local and state elections. That includes a 2022 run for mayor against Johnson and five others in which she won 315 votes or 0.51% of the votes, according to the city Election Commission.

She accused Johnson and Crowley of using their current positions as stepping stones to advance their political careers.

“Their interests are not for the people, first and foremost,” she said. “It’s about the position and acquiring a higher position and higher status.”

Would Crowley pursue a run for governor if Tony Evers doesn't run again?

Pressed on whether he would run for governor in the middle of a second term if Gov. Tony Evers were not to seek re-election in 2026, Crowley said he backed Evers and was committed to serving out his term as he did "not think there's a seat open for me at this moment."

Still, Crowley did not outright reject the possibility of a run.

"I couldn't answer that until we crossed that path. But, honestly, at this moment it is something that I would seriously consider if the opportunity came, but at this moment, I am strictly, strictly focused on being the county executive of Milwaukee County,” he told the Journal Sentinel.

Johnson was mum even to the hypothetical of running for higher office.

"I think many people are talking about some statewide office as it relates to either of us, but right now my goal, seriously, is to run for re-election and have the opportunity to serve a full term as mayor," he said.

Alison Dirr can be reached Vanessa Swales can be reached at

This article originally appeared on Milwaukee Journal Sentinel: Big wins put Cavalier Johnson, David Crowley in political sweet spot