Jake Zimmerman knows people have been jokingly questioning his sanity since he ran for St. Louis County assessor 15 years ago.
"I was running on a little bit of a cleanup mission," he said of the 2011 effort to be the first elected assessor in more than 50 years. "And I do feel a little bit the same way about broader St. Louis County government right now."
Zimmerman has been involved in politics and political spaces since 2002, when he was hired to join the consumer protection division of the attorney general's office. From there, he joined Gov. Bob Holden's administration as deputy legal counsel.
David Cosgrove, managing partner at the Cosgrove Simpson law firm, was Zimmerman's boss in the attorney general's office, and picked him to join the Holden administration. He remembers Zimmerman as a genuine, straightforward individual who worked incredibly hard.
"I think he's going to have the energy and the intellectual capacity to swing at every pitch that comes his way and hit the ball," Cosgrove said.
Zimmerman had a short stint in the private sector after Holden left elected politics, then ran for state representative in a district centered around his hometown of Olivette in central St. Louis County. He's been in elected office of one form or another, often winning in landslides, since 2007.
The county's budget path
There are a lot of curveballs coming the way of whoever is the next county executive. The trickiest is likely to be the budget, which could more accurately be described as a "sinker." Zimmerman does not sugarcoat the size of the problem.
"The county, on its current trajectory, is on a path to bankruptcy," he said. "If this is not right-sized soon, the people of St. Louis County are going to face damaging and unconscionable cuts."
The reserves used to close years of deficits are close to running out and federal money that helped sustain the county through the COVID-19 pandemic is no longer available. The county has already reduced the hours its headquarters and satellite offices are open. County Executive Sam Page's proposed budget for 2027 has a $65 million deficit without new revenue or the use of one-time funds, even with the elimination of 139 positions.
Page has even talked about the possibility of cutting police officers, something Zimmerman calls an unproductive bluff.
Unlike his opponent, Republican County Councilman Dennis Hancock, R-Fenton, Zimmerman is willing to include tax increases in the budget conversation.
"I don't think you cut your way to prosperity. I think that the people care a lot about the services we provide," he said. "There are ways you can fix your customer service and do more with less. And I have some experience doing that in my current office. But I don't want to pull the wool over anyone's eyes. You're not going to get there by getting rid of waste, fraud and abuse alone."
A tax on online purchases makes the most sense as a revenue source to Zimmerman.
"I think most sensible people would agree that taxing in a way where you don't discriminate against local businesses is a pretty good idea," he said.
Voters have rejected such a tax twice in the past four years, most recently in August. That result did not surprise Zimmerman.
"Before you ask the people for more money or ask the elected representatives of the people for more money, it helps for the people to have some trust in what's going on and believe that that money will be appropriately spent," he said.
Restoring trust in government
There have been a lot of reasons for people to distrust county government over the last seven years, he said. Steve Stenger went to prison in 2019 for trying to steer contracts to a campaign donor. Page and the county council have been feuding since COVID. The Department of Revenue spent millions of dollars on a software system that did not work.
"When I look at all of the stuff that needs to be fixed and the wrongs that need to be righted in county government, and I see elected officials just squabbling with one another over nonsense, that triggers something in me," Zimmerman said.
Zimmerman and Hancock are both running as the candidate to stop the fighting between Page and the council and restore a working relationship between the executive and legislative branches. Zimmerman points to his 15 years in the assessor's office to make his case.
While people may not always be happy with their property tax bill, he said, he has run the office without scandal or drama.
"I take no small amount of pride in the fact that I've run my piece of county government with honesty and integrity," he said. "That's a calling card that I have."
The 2026 campaign
Zimmerman took his first swing at the county executive seat in 2020, losing in the Democratic primary to Page. He calls it the strangest election he'd ever been a part of because of COVID.
"I was running for this office largely from the comfort of my own home," he said. "Say what you will about this campaign season, and it's been a doozy of a campaign season, but there are parades to go to and hand out candy. There are public town hall meetings. I really missed that six years ago."
The 2026 Democratic primary for county executive was a bruising and expensive three-way contest. Although Zimmerman walked away with the win, more Democrats supported his opponents.
Most will likely vote for Zimmerman as the party's candidate in the general election. But others, like former state Rep. Bob Burns, are supporting Hancock instead.
"I'm not saying Jake Zimmerman is bad. I don't think he will be a bad county executive if he wins," Burns said. "But I think that Dennis Hancock would be a better county executive, and I think it's time for a change."
Hancock is targeting disaffected Democrats as part of his campaign strategy, and Zimmerman is aware of the electoral math. But his message does not waver.
"I work for everybody," he said. "It doesn't matter if you voted for me or not. Doesn't matter if you're a Democrat or a Republican. The job here is to solve some problems and balance a budget and get people working with each other again."
In the last weeks of the election, Zimmerman is taking that message on the road to smaller private gatherings and quick appearances at meetings of supportive groups. He's also using the time to tout Democrats up and down the ballot.
But he dismisses any suggestion that he's taking the outcome of his race for granted.
"I take all opponents seriously," he said. "I have a lot of respect for Councilman Hancock. I think we're going to have a fair and an honest conversation, and I hope to do this right."
Editor's note: A profile of Hancock ran Wednesday.
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