From Washington to the Wynn Las Vegas: A look at some places County Executive Johnny Olszewski has been in 2023

In the nine months since assuming his second term as Baltimore County Executive, Johnny Olszewski Jr. has partied with state officials in Las Vegas and lunched with Orioles General Manager Mike Elias at a private Towson country club. He’s sipped Guinness at a Halethorpe brewery with U.S. Sen. Chris Van Hollen, and toured the White House with President Joe Biden.

While his office regularly promotes some of his appearances and public events, The Baltimore Sun obtained a more detailed look at Olszewski’s schedule between Jan. 1 and Sept. 21 via a Maryland Public Information Act request.

Olszewski, whose final term expires in 2026, is believed to be considering a run for Congress if U.S. Rep. Dutch Ruppersberger retires. Rupersberger, a former Baltimore County Executive himself, represents the 2nd Congressional District, which contains parts of Baltimore and Carroll counties and a part of Baltimore City.

“Dutch has been a very close friend of mine for a long time, and I’ve supported him. He supported me. We work together very closely. I know he has yet to make a determination about his political future,” Olszewski said. “In the meantime, we’re focused on delivering the best results we can for our residents.”

Other Maryland congressional delegation members, like Rep. John Sarbanes and Sen. Ben Cardin, have announced their intentions to step down in recent months. The 6th District, currently represented by Rep. David Trone, who is vying for Cardin’s seat, and the 3rd District, currently represented by Sarbanes, are both up for grabs as well as a U.S. Senate seat in the 2024 election.

Olszewski’s schedule reveals previously unreported activities, like several meetings with Orioles executives; a phone call with former Gov. Larry Hogan; and a Cabinet meeting with Biden. He also met weekly with lobbyists, state politicians, and business leaders, which political science professor Roger Hartley surmised was to gather support and endorsements.

Ruppersberger has not yet decided if he will seek a 12th term, according to spokesperson Jaime Lennon. The primary election filing deadline is Feb. 9 and the primary is May 14.

Olszewski, 40, declined to comment about his aspirations for higher office, but has retained Sophia Silbergeld, an Adeo Advocacy strategist who previously advised Gov. Wes Moore and Comptroller Brooke Lierman on their campaigns.

“I’ve said pretty consistently that if there’s an appropriate opportunity to expand, elevate, and highlight the incredible work that we’ve done here in Baltimore County, we would certainly look for opportunities to do that,” Olszewski said.

Cultivating relationships

Olszewski’s first publicly noted meeting with Orioles staff in 2023 was a Feb. 10 lunch date with Elias at the exclusive L’Hirondelle Club in Towson. Olszewski then attended a May 21 dinner hosted by Orioles Chairman and CEO John Angelos at the upscale Delilah at Wynn Las Vegas restaurant during the International Council of Shopping Centers conference.

There, the county executive met with developers like Lutherville Station developer Mark Renbaum and Howard Perlow, the organizer of the annual Las Vegas conference known as the Maryland Party.

State officials are negotiating a binding lease with Angelos by the end of the year that would keep the team in Baltimore. As a non-city official who does not have a position on the Maryland Stadium Authority, which manages publicly-owned stadiums like Camden Yards, Olszewski has little leverage to entice Angelos to keep the Orioles in the city.

He discussed over lunch with Elias the upcoming Orioles season, but they did not talk specifically about club operations, Olszewski said.

“I recognize I don’t have a decision-making role in what’s happening with the stadium conversations, but just generally, these are relationships I’ve tried to cultivate and maintain over the years,” Olszewski said, “Both with the Ravens and the Orioles.”

Angelos declined to comment via a spokesperson.

Shoring up support

Though he spent most of his time in Baltimore County, Olszewski spent 24 days in Annapolis, meeting with elected officials and lobbyists and testifying before the General Assembly on matters ranging from protecting access to reproductive care to regional oversight of water infrastructure. He also made trips to Washington, D.C.; Austin, Texas; and St. Louis, Missouri.

He frequently met with Del. Ben Barnes of Anne Arundel and Prince George’s counties, Del. Luke Clippinger of Baltimore City, and state Sen. Guy Guzzone of Howard County, all Democrats he served with when he was a Dundalk-area delegate from 2006 to 2015.

Other frequent recipients of Olzewski’s time included State Treasurer Dereck Davis, with whom he discussed the future of the Pikesville Armory and the North Point Government Center in Dundalk, and Alexandra Hughes, an Annapolis strategist who previously served as chief of staff for House Speaker Adrienne A. Jones and former House Speaker Michael Busch.

Under federal law, Olszewski cannot represent himself as a candidate or spend more than $5,000 without officially filing to run for office. He cannot transfer to a federal campaign any of his state political campaign’s $1.6 million in funds.

Because of those limitations, Olszewski is likely “doing everything he can to secure” endorsements from potential allies, said Hartley, the dean of the University of Baltimore’s College of Public Affairs.

“At this stage in the game, [his strategy] may not be super specific,” Hartley said. “It might be if there’s a particular project that a delegate has been trying to get federal support for. Asking in the initial conversation would be the smart thing to do: ‘What are your priorities? What do you need for your district?’”

Olszewski said the meetings were to maintain relationships he had forged during his time in Annapolis.

Hughes “and I have been friends for a very long time … back when I was a 23-year-old member of the House of Delegates,” Olszewski said. “So whether it’s a staff person with whom I continue to cultivate and spend time with or, you know, members of the legislature, these are folks that I started with in the legislature, have become very close to, and do try to carve out time to spend time with.”

The treasurer would likely support Olszewski if he runs, but Davis “will wait to see the full slate of candidates” before making a final decision, said Shareese Churchill, the treasurer’s spokesperson. “He has a relationship with the county executive, dating back to when they served together on the House Economic Matters Committee.”

Larry Hogan also wished him “well in his future endeavors,” Olszewski said when asked about an Aug. 10 call between him and the former Republican governor. Hogan is advising Foresite Development, which is redeveloping the former CP Crane power plant site in Bowleys Quarters.

A Hogan spokesperson did not respond to a request for comment.

‘Shared challenges’

Olszewski and his staff spent five days in Ocean City in August for the summer Maryland Association of Counties convention, and went to Austin in July for the annual National Association of Counties conference.

Much of the three days in Austin was redacted from his schedule, save for a roundtable breakfast, an Aetna-sponsored dinner and reception, and a dinner reservation for six at French eatery Justine’s Brasserie.

He also visited Washington, D.C., on four occasions, staying overnight once, where he met President Joe Biden in the White House Cabinet Room on Feb. 14 during the National Association of Counties’ legislative conference.

The purpose of a jaunt to St. Louis in September was to speak with officials about “best practices and shared challenges,” since St. Louis, like Baltimore County, has an independent county government arrangement, according to press secretary Erica Palmisano.

Baltimore Sun reporter Jeff Barker contributed to this report.