Johnny Olszewski is facing tough questions over a 4-year-old case

A few months ago, Johnny Olszewski Jr. It seemed untouchable.

After becoming the youngest county executive in Baltimore County history, the Dundalk Democrat handily won reelection in 2022. Earlier this year, he coasted to victory in his party’s primary for a rare open seat in Congress, then got a shoutout from President Joe Biden at a press conference after the Key Bridge collapse. “Johnny Oooh, I like that” Biden said with a grin, acknowledging the rising Democratic star.

The 41-year-old Olszewski is heavily favored to win the general election against a perennial candidate who’s never held elective office.

Then, new stories resurfaced from a 4-year-old case in which the county approved a payment for a retired county firefighter who is the brother of one of Olszewski’s friends, and who also happens to be his real estate agent.

That same friend, John Tirabassi, works for a trucking company that the county bought $4 million worth of dump trucks from in 2023 and 2024. The revelations, first reported in The Baltimore Sun and the Baltimore Brew, prompted the Maryland GOP to call for Olszewski to resign as county executive and withdraw from the 2nd District congressional race.

“Johnny Olszewski has no business continuing to serve as Baltimore County Executive, let alone continuing his campaign for Congress,” Maryland Republican Party Chairwoman Nicole Beus Harris said in a statement circulated Wednesday evening. “If he refuses to do the honorable thing and drop out, we will be working every day between now and November to expose his corruption to voters, and defeat him at the ballot box.”

Olszewski is running against Republican Kim Klacik, a conservative talk-show host endorsed by former president Donald Trump who has called Olszewski an “illegal alien sympathizer.” She has run twice for Congress and lost; many do not see her as a serious threat. The GOP’s call for his resignation does not change that calculus, said Asa Leventhal, Olszewski’s campaign manager.

“The Maryland Republican Party continues to desperately grasp at straws to find any reason to distract voters from candidates like Kim Klacik who back the extreme policies of Donald Trump — a convicted felon,” Leventhal said. He added a phrase that the county executive often invokes, calling the “Johnny O” administration the most transparent in county history. Olszewski was out of town and not available for comment beyond the statement, Leventhal said.

The Baltimore County Council is made up of three Republicans and four Democrats. Councilman David Marks, an Upper Falls Republican who has served on the council since 2010, said that the Republican members generally work in a bipartisan manner with their Democratic colleagues and Olszewski.

“The chairman of the Maryland Republican Party has not spoken to me in years, nor did she ask for my opinion,” Marks said.

Maryland Republican Party Executive Director Adam Wood said he did not contact any of the council members. Asked if he thought his call for Olszewski’s resignation would jeopardize the working relationships of Republican council members with the county executive, Wood said, “I would say secret payments would make their working relationship difficult.”

Marks said constituents have expressed concerns about him about the payout to the former firefighter, and that he has his own concerns.

He said he would like the county’s inspector general, Kelly Madigan, to look into the matter and “publicly offer her findings as soon as possible.” Reached on vacation Thursday, Madigan said she would neither confirm nor deny an investigation into the matter.

The Brothers Tirabassi

The recent criticism of Olszewski dates back to 2020, when Baltimore County firefighter Philip Tirabassi sought to transfer retirement credits from an earlier job as a city firefighter to increase his county pension benefit. He had served in the city for 2.8 years, records show. County officials repeatedly denied his request, saying the deadline had long passed for the transfer.

At some point, though, an attorney who is no longer with the county approved what Olszewski told The Sun was an “unauthorized agreement” allowing the credits to transfer. The county tried to back out of it, and Tirabassi threatened to sue. The county ultimately paid Philip Tirabassi $83,675 to settle after attorneys for the retirement system told officials that letting Tirabassi keep the credits would jeopardize the system’s tax-exemption status. County officials have said they thought settling the matter privately would be cheaper.

That might have been the case if not for Fred Homan, a former county administrator Olszewski had asked to resign in 2018. Homan sued the county for records related to the Tirabassi case. The county has spent up to $318,000 to date fighting the disclosure of those records, according to county officials, and the council recently authorized the county to spend up to $200.00 more if necessary. Since a judge directed the county to turn over the records to Homan, details relevant to the case have been unspooled in The Sun and the Baltimore Brew.

The news outlets recently reported that, despite Olszewski’s claim that he “did not have a close personal relationship with Philip Tirabassi,” Olszewski and his wife used Philip Tirabassi’s real estate company, Advance Realty Direct, to buy and sell three properties in recent years.

John Tirabassi, Philip’s brother, was a classmate of Olszewski’s from Sparrows Point High School and his real estate agent at Advance Realty Direct. John Tirabassi is also a regional sales representative for Peterbilt, a trucking company with a local office in Dundalk. In 2023 and 2024, the county spent $4.2 million to buy 16 dump trucks from Peterbilt, The Sun reported.

Integrity ‘speaks for itself’

Don Mohler, Olszewski’s predecessor and a longtime staffer for previous county executives, said the dump-trucks decision likely had nothing to do with Olszewski.

“Baltimore County executives go nowhere near the procurement process,” said Mohler, adding that he’s known Olszewski since he was a high school student.

“His integrity speaks for itself,” he said. “And for anyone to suggest that the Baltimore County executive would do something unethical, they just don’t know this man.”

While the Tirabassi disclosures have brought the most public scrutiny of Olszewski, they are not the only examples of an occasional rocky tenure. The council did not have all of the information when members approved the settlement with the former firefighter, originally filed under the name “Philip Dough” instead of the more recognizable Tirabassi.

The council, led by Chair Izzy Patoka, a Democrat, has also been frustrated with what some consider a lack of transparency from the county executive this year. The council approved the purchase of an office building at 305 Washington St. in Towson for $5.8 million. The 30-year-old office building was assessed at $4.1 million, according to state tax records. At one time, the building was owned by Blue Ocean, a company that the county executive’s father, John Olszewski, was a lobbyist for in 2020. Blue Ocean sold it to 305 Washington LLC in 2019; it’s unclear who owns that entity now.

The elder Olszewski did not return a call for comment. The Baltimore County ethics office told the senior Olszewski that the work was not a problem because he was lobbying at the state level, not the county level.

The council approved the sale in large part because the county had declared the building was move-in ready. Instead, the building required nearly $7.5 million in repairs. Patoka chastised top county officials for keeping the council advised on a “need-to-know basis” about important expenditures.

Madigan, the inspector general, also said in a recent report that the county executive needed to inform the council when it rehires retirees, which it had not been consistently doing, in violation of its own rules.

His press releases and social media presence do not indicate anything is amiss with his plans to glide into the seat being vacated by Democrat Dutch Ruppersberger, who has served in Congress since 2003. The district covers parts of Baltimore and Carroll counties and a small section of Baltimore City.

This week, Olszewski announced the appointment of nine community members to lead a public-engagement effort regarding the long-standing dredging project on Hart-Miller Island. Olszewski, who often touts his working-class roots, shared his pride on Twitter that Towson’s Apple Store was the first to unionize, and also posted about winning an endorsement from former Congresswoman Gabby Giffords’ PAC, which focuses on reducing gun violence.

Wood said the Maryland GOP wouldn’t be calling for Olszewski’s resignation if he had been as transparent as promised. In trying to keep the records related to Tirabassi private, his administration ended up costing taxpayers far more than the original settlement.

“When somebody expends that much money to not be transparent, that is very concerning,” Wood said. “Especially when it’s taxpayer money.”

Reached Friday afternoon, Homan, who filed the initial lawsuit that brought the Tirabassi case to light, declined to comment on whether he thinks Olszewski should resign.

”That kind of decision belongs to the public at large,” Homan said. “I did it because they broke the law and I wanted them to fix it.

Baltimore Banner staff writers Saul Pink, Pamela Wood and Bria Overs contributed to this story.