Maryland Matters: Olszewski Raising Funds For Congressional Run, Awaits Ruppersberger's Decision


Baltimore County Executive Johnny Olszewski delivers his fiscal year 2024 budget message to the Baltimore County Council. (Credit: Baltimore County Government)

BALTIMORE COUNTY - As U.S. Representative Dutch Ruppersberger (D-2nd) remains silent on whether or not he will seek another term, Maryland Matters reports that Baltimore County Executive Johnny Olszewski Jr. (D) is quietly preparing for a potential run for Ruppersberger's seat.

Ruppersberger has yet to confirm his intentions to run for a 12th term, sparking another round of theories surrounding Olszewski. In May, Maryland Senator Ben Cardin announced that he would not seek reelection in 2024, opening Pandora's box of speculation about who would run for the seat.

Olszewski ultimately did not throw his hat in the ring, opting to support Prince George's County Executive Angela Alsobrooks. Despite declining to run, the young democrat's political aspirations have long been evident.

In 2014, before becoming a county executive, Olszewski lost a race for state senate to Republican newcomer Johnny Ray Salling. In 2022, Olszewski considered running for governor but ultimately sought a second term as county executive. He won reelection in a landslide, securing 64% of the vote and further solidifying his position as a prominent figure in local politics.

New information from Maryland Matters has again thrust Olszewski into the political speculation spotlight. According to the news service, he has enlisted the help of renowned Baltimore fundraiser Sophia Silbergeld and commenced fundraising operations for a statewide campaign.

Silbergeld, a political consultant with Adeo Advocacy and the lead fundraising strategist for the 2022 campaigns of Gov. Wes Moore, Comptroller Brooke Lierman, and Attorney General Anthony Brown, clarified to Maryland Matters that these steps are contingency preparations, not a direct challenge to Ruppersberger's incumbency.

"He would never challenge him or do anything to make the congressman uncomfortable," Silbergeld said.

Silbergeld declined to disclose the total amount raised but added, "The response has been very positive."

Olszewski is not officially registered with the Federal Elections Commission but has accumulated funds via what Silbergeld describes as "an un-filed exploratory committee," allowed under federal election law for a candidate exploring a potential candidacy.

77-year-old Ruppersberger, who served two terms as Baltimore County executive before his first election to the House of Representatives in 2002, has yet to announce his 2024 election plans. Despite his silence, Maryland Matters reports that as of March 31, his campaign account held $938,284, with $150,671 raised in the first three months of 2023.

Should Ruppersberger decide to run for another term, funds raised by Olszewski could be used in the subsequent election cycle, contingent on the approval of donors.

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Johnny Cliche looking to take his failed leadership to a higher level. What a clown show. The guy is clueless. So now he aspires to destroy more people’s lives. He should resign and never seek any political position. He’s a failure.

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