Milwaukee County Executive David Crowley is headed to the Governor’s Mansion after a massive Democratic wave swept the party into power in Wisconsin, delivering Democrats their first governing trifecta in 16 years.
But before Crowley can be sworn in as governor, he’ll have to resign as Milwaukee County Executive, triggering a special election to replace him in one of Wisconsin’s most reliably Democratic counties.
Under state law, Milwaukee County Board Chairwoman Marcelia Nicholson-Bovell would initially assume the duties of county executive before the County Board appoints an interim replacement within 30 days.
Within seven days of Crowley’s resignation, the county clerk must order a special election. If the vacancy occurs after October 31 but no later than 49 days before the February spring primary, the special election would coincide with Wisconsin’s regularly scheduled spring elections.
Assuming Crowley resigns by December 29, Milwaukee County voters would head to the polls this spring to select a new county executive to serve the remainder of his term, which expires in 2028.
Crowley was first elected in 2020 after longtime County Executive Chris Abele declined to seek reelection. He narrowly defeated Democratic State Senator Chris Larson by approximately 1,100 votes after both candidates emerged from a four-way primary. Crowley faced only token opposition in 2024, cruising to reelection with nearly 85% of the vote.
With the position opening up again, expect no shortage of Milwaukee Democrats to consider throwing their hats into the ring.
The job comes with a $140,000 annual salary, considerable influence over Milwaukee County government, and the potential to serve as a springboard to higher office.
Although Republicans could field a candidate, Milwaukee County’s overwhelmingly Democratic electorate makes it likely that the race will ultimately come down to two Democrats.
Here are five names worth watching.
1. Marcelia Nicholson-Bovell
Perhaps the most obvious contender is Milwaukee County Board Chairwoman Marcelia Nicholson-Bovell, who would temporarily assume the duties of county executive following Crowley’s resignation.
Long considered a rising star in Milwaukee Democratic politics, Nicholson-Bovell has already signaled her intention to run, telling Milwaukee Magazine in October that she was committed to seeking the position.
At just 34 years old, Nicholson-Bovell has already established herself as one of the most influential figures in Milwaukee County government. As County Board chairwoman, she has been closely involved in shaping county policy and overseeing the legislative branch of county government.
She would also be a logical choice for Democratic Party leaders looking to cultivate the next generation of statewide political talent. A young, biracial woman with deep ties to Milwaukee’s Democratic establishment, Nicholson-Bovell checks many of the boxes party leaders have increasingly prioritized.
Politically, she has been closely aligned with Crowley throughout his tenure, including joining him for a cake-cutting ceremony celebrating legislation that nearly doubled Milwaukee County’s sales tax.
That relationship could prove particularly valuable in a crowded special election.
Although it’s unclear whether Crowley would formally endorse Nicholson-Bovell, she would likely benefit from his political network and relationships with influential Milwaukee Democrats.
Of the names on this list, Nicholson-Bovell appears to have the clearest path to becoming Crowley’s successor.
2. State Senator Chris Larson
If Nicholson-Bovell is the establishment favorite, State Senator Chris Larson could emerge as her most formidable challenger.
Larson has already come tantalizingly close to winning the job, losing to Crowley by approximately half a percentage point in the 2020 election.
It wasn’t his first attempt, either.
Larson challenged then-County Executive Chris Abele in 2016, making a potential 2027 campaign his third attempt at the office.
An outspoken progressive who has often aligned with the socialist wing of his party, Larson has never been shy about pursuing higher office. Beyond his two county executive campaigns, Larson briefly entered the 2022 U.S. Senate race and has previously floated bids for Milwaukee mayor and governor.
A fixture of Milwaukee’s progressive political movement, Larson has frequently clashed with more moderate members of his own party. He has positioned himself as an unapologetic champion of left-wing priorities, and is basically a walking, talking BlueSkySocial feed.
For years, Larson has appeared eager to move beyond the State Senate, where Republicans have largely prevented his progressive agenda from advancing.
But that political calculation may have changed overnight.
With Democrats now controlling the governor’s office and both chambers of the Legislature for the first time in Larson’s legislative career, he finally has an opportunity to advance policies that previously had little chance of becoming law.
On the other hand, the county executive position pays more than twice a state senator’s legislative salary and would give Larson considerably more executive authority.
If he runs, Larson could quickly consolidate support from Milwaukee’s increasingly influential socialist and progressive movements, potentially setting up a contentious battle with the Democratic establishment.
Larson wouldn’t have to surrender his safely Democratic Senate seat simply to run, giving him a relatively risk-free shot at the office.
The question is whether he’s willing to risk a third defeat for county executive or would rather remain in Madison, where Democrats finally have the votes to advance his progressive agenda.
3. Joel Brennan
Joel Brennan’s gubernatorial campaign wasn’t exactly one for the history books.
In a crowded Democratic primary dominated by more progressive personalities, Brennan attempted to carve out a lane as a moderate, business-friendly Democrat. His pitch centered on executive experience, pragmatism, and his potential electability as a self-described “boring white guy.”
Democratic primary voters weren’t particularly interested.
Brennan finished fourth with just 4.68% of the vote, placing last among the candidates who remained in the race.
Hardly the momentum a politician hopes to carry into another campaign.
Still, Brennan could be a sleeper candidate for Milwaukee County Executive.
Despite his disappointing gubernatorial showing, Brennan emerged from the campaign with greater name recognition and an expanded fundraising network. More importantly, his professional background makes him uniquely positioned to appeal to Milwaukee’s business and civic establishment.
As president of the Greater Milwaukee Committee, Brennan maintains extensive relationships with some of the region’s most influential business leaders, employers, and philanthropic organizations.
He also brings considerable government experience.
Brennan previously served as secretary of the Wisconsin Department of Administration under Governor Tony Evers and held leadership positions in Milwaukee city government under former Mayor Tom Barrett, a longtime political mentor.
That résumé could allow Brennan to present himself as a county executive in the mold of Chris Abele: a relatively moderate Democrat focused on management, economic development, and competent government rather than progressive ideological battles.
He could also appeal to Milwaukee County’s remaining Republican and independent voters, particularly if the alternative is a more outspoken progressive like Larson. Crowley benefited from a similar dynamic in 2020, when some conservative voters viewed him as the more palatable alternative to Larson.
But Brennan would face significant obstacles.
Nicholson-Bovell would likely occupy much of the Democratic establishment lane that Brennan would seek to run in, particularly if Crowley’s political allies rally behind her. Brennan would also have to overcome his lackluster gubernatorial showing and lingering controversy surrounding comments about race and electability during the primary.
His strongest argument would be that Milwaukee County needs an experienced administrator rather than another ideological politician. Whether that message resonates with Democratic primary voters is another question entirely. It didn’t in the Governor’s race, but spring elections can be entirely different.
4. Milwaukee Alderwoman Marina Dimitrijevic
If Larson decides against a third run for county executive, Milwaukee Alderwoman Marina Dimitrijevic could emerge as a leading alternative for the progressive wing of the Democratic coalition.
Dimitrijevic represents Milwaukee’s heavily progressive Bay View neighborhood and has built her political identity around left-wing activism, environmental policy, and social justice issues.
Describing herself as a “trailblazing progressive champion,” Dimitrijevic has championed anti-ICE measures, climate initiatives, and equity-focused policies throughout her time in local government.
She also previously served as the chairwoman of the Milwaukee County Board, which is currently occupied by Marcelia Nicholson-Bovell.
Before joining the Milwaukee Common Council, Dimitrijevic served as County Board chairwoman, giving her firsthand familiarity with county operations, budgeting, and the sometimes contentious relationship between the board and county executive.
She’s no stranger to seeking higher office, either.
Dimitrijevic ran for Milwaukee mayor in the 2022 special election following Tom Barrett’s departure, finishing fourth in a primary ultimately won by Cavalier Johnson.
Although she’s been a fixture in Milwaukee progressive politics for well over a decade, Dimitrijevic has never quite broken through as a major political force beyond local government. Still, the political environment may be more favorable to her than ever.
With democratic socialist and progressive candidates gaining influence in Milwaukee and other major cities, Dimitrijevic could attempt to capitalize on the movement’s growing political strength.
It’s hard to see Dimitrijevic run against Chris Larson, who is a bigger name with a bigger constituency occupying the same political lane.
Both would likely compete for many of the same progressive activists, donors, and voters, potentially splitting the left-wing vote and clearing a path for a more establishment-friendly candidate.
But if Larson stays in Madison, Dimitrijevic could find herself with an opening.
5. Mandela Barnes
Now, let’s have a little fun.
Following his controversial departure from the Democratic gubernatorial primary, former Lieutenant Governor Mandela Barnes suggested he might be ready to “burn it all down.”
And if Barnes really wants to shake up Wisconsin Democratic politics, what better place to start than by taking David Crowley’s old job?
Barnes has made little effort to conceal his frustration with Crowley or the Democratic establishment that rallied around him. After a bitter gubernatorial primary that ended under disputed circumstances, Barnes has plenty of reasons to harbor political grudges.
A campaign for Milwaukee County Executive would offer an opportunity to settle a few scores while simultaneously resurrecting his political career.
Of course, there are some obvious problems with that plan.
Barnes lost a high-profile U.S. Senate race to Republican Ron Johnson in 2022 before mounting a disappointing gubernatorial campaign four years later. Even before his controversial withdrawal, polling suggested his path to the Democratic nomination was narrowing.
Convincing voters to give him another opportunity so soon could be a difficult sell. But if there’s anywhere Barnes could stage a political comeback, Milwaukee County might be the place.
As a former lieutenant governor and U.S. Senate nominee, Barnes would enter the race with considerably more name recognition than virtually any other prospective candidate. He also maintains a following among progressive activists, even if his relationships with Milwaukee’s Democratic power brokers have become increasingly strained.
And that’s what makes the possibility so entertaining.
Imagine Barnes launching a campaign against Crowley’s preferred successor, turning a relatively predictable local special election into a proxy war over the future of Milwaukee’s Democratic Party.
Would he actually do it? Probably not.
Barnes could instead set his sights on challenging Milwaukee Mayor Cavalier Johnson in 2028 or wait for an opportunity to succeed longtime Congresswoman Gwen Moore.
It’s also entirely possible that, following the “shady stuff” he alleges occurred during his latest campaign, Barnes decides he’s had enough of electoral politics altogether.
But if Mandela Barnes really wants to burn it all down, taking David Crowley’s old job would certainly be one way to light the match.
Honorable Mentions
Glendale Mayor Bryan Kennedy: A longtime Democratic activist in Milwaukee County, Kennedy attempted to run for county executive in 2020 but was disqualified from the ballot over problems with his nomination papers. His experience in local government and familiarity with county politics make him another potential contender.
County Board Supervisor Steve Taylor: Taylor chairs the County Board’s Finance Committee and represents the Franklin area. One of the few county supervisors who identifies as a conservative, Taylor has experience with county budgeting and fiscal oversight. However, his divisive reputation among some local Republicans, combined with Milwaukee County’s overwhelmingly Democratic electorate, makes a successful countywide campaign a steep uphill battle.
Former State Representative Sylvia Ortiz-Velez: An independent-minded Democrat who has frequently clashed with her own party, Ortiz-Velez lost her Assembly primary after Democratic Party leaders backed her opponent amid a series of public political disputes. A former county supervisor with roots in Milwaukee’s heavily Hispanic south side, Ortiz-Velez has both county government experience and a willingness to challenge the Democratic establishment. Whether she has the political organization to mount a competitive countywide campaign is another matter.
