For over a decade, Baltimore County Executive Johnny Olszewski Jr. has made it a point to engage with his constituents. He’s met them after panels at nearby colleges. He’s grabbed coffee with them at local senior homes. He’s knocked on their doors and chatted with them about the future of the region.

His work has paid off.

Olszewski has ascended from a public school teacher two decades ago to the upper echelons of state and local politics. He served as a state delegate from 2006 to 2015 and has been county executive since 2018. Now, he is vying for another promotion through a rare open congressional seat on his home turf, where he has a large political advantage as a Democrat.

Olszewski hasn’t always had this much political momentum. In 2014, he lost a state Senate race to Republican Johnny Ray Salling. And, when he ran for executive in 2018, he edged the Democratic primary runner-up, state Sen. Jim Brochin, by nine votes. In that race, both presented themselves as reformers of a pay-to-play system that favored developers.

Olszewski’s ability to connect with voters through direct community outreach brought him over the edge, said Nina Kasniunas, an associate professor at Goucher College. “He will stop and talk to people,” she said. “People want to vote for someone that they trust, and if you can connect with a voter, that takes you halfway there.”

Olszewski took the county’s top job promising progressive policies, transparency and “a better Baltimore County” — his campaign slogan. He spearheaded a local and state law that prevented income-based housing discrimination. He brought an inspector general to the county. And he supported a push for a larger and more diverse County Council.

But now Olszewski comes to voters with dents in his armor. A series of news stories have unspooled convoluted backroom deals that have put his management of taxpayer dollars into question.

First, the county secretly paid a former firefighter $84,000 after backing out of a legally questionable agreement to increase the firefighter’s pension benefits. Then the county was poised to spend $300,000 on a storm drain system — first proposed in 2000 — in his Chesapeake Bay neighborhood until around 2022, when the local government shelved the project.

Is the executive still the venerable man he made himself out to be years ago?

Olszewski thinks so. His camp has contended that these dealings are a nothingburger.

“I hope that folks who have looked over the totality of my career see that I am someone who has been responsive,” he said in an interview. He boasted about his accomplishments in office, including his investments in school construction and parks.

But Republicans have quickly labeled him as another corrupt Democrat clawing for national power.

Kim Klacik, his Republican opponent whom former President Donald J. Trump backed in a 2020 congressional bid, has repeatedly blasted the executive on X for “corrupt behavior.”

“When I speak to voters, there are some that are saying, ‘I just can’t imagine promoting him to the federal level considering what he’s done as a county executive,’” Klacik said. “Whether it was with taxpayer dollars, that secret pension payment, things like that.’”

Klacik says she’s focused on positioning herself as more trustworthy than Olszewski.

“There are some people that probably feel that they don’t know me very well,” she said. Klacik has never held public office. “I’m looking at it as: He has a poor record where I have no record at all. People are going to have to think, ‘Do we choose who we know or the person that we don’t know and hope that they are better?’”

He remains the front-runner in the congressional race. Maryland’s 2nd Congressional District is the state’s second-most competitive, according to Cook Political Report ratings, seven points more Democratic than national averages. The district includes portions of Carroll County and Baltimore, but the bulk of the district is Baltimore County, where voters are familiar with Johnny O and Democrats outnumber Republicans by more than 2 to 1.

Klacik became conservative famous during her campaign for a Baltimore City congressional seat in 2020. A campaign ad of her walking through Baltimore neighborhoods in red stilettos went viral in right wing circles and helped her raise millions of dollars — most of which went to the companies that produced the ad. Her bid hasn’t attracted as much attention or money this time.

That’s partly because the recent reporting on Olszewski by The Baltimore Sun, Brew and Banner hasn’t penetrated the Baltimore County zeitgeist, said Matthew Crenson, a local politics researcher at the Johns Hopkins University. Voters may be preoccupied by national and global-level political happenings. “The contest between [Kamala] Harris and Trump is so consequential that I don’t think people are ready to pay attention to anything else,” he said.

But the stories all fall under a long penumbra of county elected officials’ sketchy dealings with developers, businessmen or others with political influence. In the mid-1990s, former county executive and current Congressman C. A. Dutch Ruppersberger III — whom Olszewski could replace — allowed a developer to skirt historic protections and reconstruct one of Baltimore County’s oldest homes into an office building. And in 2017 county residents blasted executive Kevin B. Kamenetz for easing a path for developer and prominent donor Caves Valley to clear 30 trees in Towson to build a gas station.

Voters who have tuned in to the criticisms of Olszewski are likely deeply partisan politicos with rigid opinions, Kasniunas said. “New information is not going to calculate in any real way for them. They’re going to be willing to overlook that,” particularly when they have a strong bond with an elected official like Olszewski.

Philip Rismiller did not know about the questions spiraling around Olszewski’s administration until one Tuesday morning a few weeks ago — only a couple of weeks before early voting — when a Baltimore Banner reporter recited a few of them to him.

By then, Rismiller, who had lived in the county for five years, had already made up his mind about Olszewski. “I already didn’t like him based on policy stuff.” He thinks the executive is out of touch with local woes and disagrees with one of his earliest decisions to hike taxes to raise revenue.

That doesn’t mean Rismiller will go for Klacik. He says his image of the Republican candidate has been tarnished by right wing commentator Candace Owens, who accused Klacik of being a strip club “madame” who misspent campaign funds on cocaine. Klacik filed a $20 million defamation lawsuit against Owens in 2021, but her case was tossed out a year later and she was ordered to pay Owens $115,000.

“I know it’s going to sound terrible,” Rismiller said. “I probably won’t even vote for either of them.”