BALTIMORE — With less than three months to Election Day, Baltimore County Executive Johnny Olszewski Jr. is still poised to win the seat of retiring U.S. Rep. C.A. Dutch Ruppersberger in November despite calls for him to step aside.

Olszewski, 41, is the favorite to win Maryland’s 2nd Congressional District after winning his May 14 primary. His Republican opponent, Kim Klacik, has only $14,700 on hand and her national profile has waned since 2020, when former President Donald Trump boosted her online and she spoke at the Republican National Convention.

John Dedie, a Baltimore County Community College political science professor, said the settlements were unlikely to threaten Olszewski’s odds of winning, citing his hefty campaign war chest, support from the incumbent Ruppersberger, and his name recognition built up from two decades in public service.

The Baltimore County Council began searching last week for a successor to serve the remainder of Olszewski’s term, which ends in 2026, signaling members’ belief that he will prevail Nov. 5.

The 2nd District, which covers Baltimore and Carroll counties and part of Baltimore City, is considered a safe district for any Democratic candidate.

The three Republican members of the County Council said they wanted an internal investigation before taking any action, bucking an ask from the state GOP for Olszewski’s resignation.

The Maryland Republican Party called earlier this month for Olszewski to resign from office and withdraw from the race, citing The Baltimore Sun’s reporting about his financial ties to brothers John and Philip Tirabassi. Philip Tirabassi, a retired firefighter, received a confidential settlement in 2020 after he asked to transfer retirement credits to his county pension despite numerous officials saying it violated state and local law.

John Tirabassi, Olszewski’s friend and high school classmate, sold the county $4.2 million worth of dump trucks in 2023 and 2024. Olszewski said he did not know about the sale, and that the county settled with Philip Tirabassi to avoid further litigation. The council was initially not informed of Tirabassi’s settlement, which was included in an annual list of county payouts under the name “Philip Dough.”

Both brothers, who are also real estate agents, helped Olszewski and his wife buy or sell three properties between 2016 and 2020, despite Olszewski saying he did not have a “close, personal relationship” with Philip Tirabassi. During that time, Olszewski named Laura Ray, Philip Tirabassi’s onetime employee, to the county ethics commission.

Those stories prompted state GOP chairwoman Nicole Beus Harris to issue a statement Aug. 1 calling Olszewski “corrupt” and saying he had “no business” serving as county executive or running for Congress.

In a staff commentary, The Sun’s editorial board called for Baltimore County Inspector General Kelly Madigan to investigate. Olszewski has not been formally accused of or charged of any impropriety.

Madigan has refused to confirm or deny the existence of an investigation.

Asa Leventhal, Olszewski’s campaign manager, previously batted away the criticism as the GOP’s “grasping at straws,” and cited Klacik’s support for Trump, a “convicted felon.”

“While the Maryland GOP tries to distract voters with partisan attacks, those who know Johnny O best — including their own Republican members on the County Council — continue to reject the political theater,” he said in a statement Friday. “County Executive Olszewski remains laser-focused on delivering results for the people of Baltimore County and making sure that voters know the stark difference between him and his MAGA extremist opponent.”

Klacik, a Middle River radio host, lost both of her previous campaigns by double-digit margins. She received a $6.4 million surge in donations after Trump endorsed her campaign against U.S. Rep. Kweisi Mfume in 2020. Most of that money was spent on advertising and consulting fees. Klacik’s campaign carries $202,387.88 of debt, according to the Federal Election Commission.

Klacik said news of the settlement was “outrageous” but “unsurprising.”

“The 16 dump trucks Johnny purchased with taxpayer funds from his friend, John Tirabassi, for $4.2M, better glow in the dark for that price,” Klacik wrote via email. “Taxpayers and hardworking families should not only expect transparency and accountability from their government servants, but they should also demand it.”

Dedie said Olszewski’s ties to the Tirabassi brothers demanded an “aisle-one cleanup,” though it was unlikely that the stories would thwart his congressional ambitions.

“It’s only a liability if the other shoe drops,” Dedie said. “His public reputation is good, he has a family name that’s been in politics for 40 years. … The things he’s been accused of doing will become Google searches. They’ll be forgotten as quickly as they’re brought up.”

The council began its search for Olszewski’s interim successor last week. County administrative officer D’Andrea Walker is expected to serve temporarily until a more permanent person is named. WYPR reported Thursday that educational advocate Yara Cheikh, Pikesville nonprofit leader Barry Williams, and former State Sen. Jim Brochin have expressed interest. The county charter requires temporary administrative officers be a member of the majority party; Olszewski is a Democrat.

The Baltimore County GOP, which has previously criticized Olszewski, has remained silent. Chairwoman Patricia Fallon did not respond to a request for comment. Nor did the Baltimore County Democratic Party.

The three Republican members of the Baltimore County Council said calls for Olszewski’s resignation were rash.

“We have a rule here in the United States — innocent until proven guilty,” said Councilman Todd Crandell of Dundalk. “The council doesn’t have all the facts in this matter. The prudent thing to do is investigate.”

Crandell, Councilman David Marks of Upper Falls and Councilman Wade Kach of Timonium said the state GOP did not speak to them before issuing the statement.

Marks said there was “strong support” among the council for Madigan to perform a “full and thorough investigation” and offer recommendations in the future for how to handle personnel issues like Philip Tirabassi’s settlement.

“Where was the breakdown?” he said in an interview. “The inspector general should investigate. There’s a reason this office was created.”

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