Six months after saying he was considering a run for Congress, Maryland’s Housing Secretary Jake Day is still on the fence about whether he’ll challenge Republican U.S. Rep. Andy Harris.

Day’s polling showed an uphill climb for any Democrat in the deep red 1st Congressional District, even for a popular former mayor of Salisbury with military bona fides.

Meanwhile, Maryland leaders remain divided on whether to try to make the race easier for him — or any Democrat — by redistricting.

“I won’t be making any decision anytime soon,” Day said. “So much remains to be seen about the electoral map.”

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Political analysts say that, as is, the entrenched Republican stronghold would be hard to flip — even for a candidate who can raise money and draw attention, like Day. But folding in some bluer areas could be a “game changer” for any Democrat.

Maryland is one Democratic-majority state poised to respond to the domino run ofredistricting efforts spurred by President Donald Trump in GOP-controlled state legislatures.

Some top Maryland Democrats appear ready to start discussions, including House Speaker Adrienne A. Jones, who has the power to kick off the process. Gov. Wes Moore has said he’s willing, too, but they’d need a partner in state Senate President Bill Ferguson to finish the job. So far, Ferguson has been more reserved on the subject.

In 2024, Trump won Maryland’s 1st District, which includes the Eastern Shore, Harford County and portions of Baltimore County, by nearly 17 points. There hasn’t been a House race won across party lines with a spread that wide, said Jacob Rubashkin, deputy editor of the nonpartisan newsletter Inside Elections.

“The baseline partisanship is incredibly, incredibly difficult to overcome,” he said.

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A Democratic candidate would need to peel off a large swath of unaffiliated voters and moderate Republicans through retail politicking, according to Rubashkin.

“Stranger things have happened,” he said. “But there’s a very clear trend here, and it’s one that speaks against any Democrat winning this seat.”

Day’s poll showed as much. Republicans strongly favored Trump and Harris. And they favored Harris over any Democratic candidate by double digits. When pollsters introduced the backgrounds and messaging of possible candidate Day compared to Harris, some respondents shifted into the “undecided” camp, making the race a statistical tie.

The movement from some Republicans was encouraging, Day said, but not enough to shift his priorities away from fulfilling Moore’s housing agenda.

He’s not walking away from the idea — yet — because he believes the people of the 1st District “deserve better” representation. He’s also concerned about the future of democracy and what he’s seeing in a Republican-controlled Congress and White House.

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“To put a fine point on it: That means flipping some seats and changing the balance of power in the House,” he said.

Democrats have won the 1st District just once in the past three decades, when Frank Kratovil Jr. rode President Barack Obama’s wave to office in 2008. Harris defeated Kratovil two years later and has enjoyed a 15-year run since.

Maryland Gov. Wes Moore shares words with Jake Day, the state housing and community development secretary, before he signs into law legislation about housing during a ceremony at the State House in Annapolis on Thursday, April 25, 2024.
Jake Day serves as Maryland Gov. Wes Moore’s housing and community development secretary, executing the Democratic governor’s housing policy around the state. (Pamela Wood/The Banner)

The number of registered Democrats has declined in the district since 2008, while Republican registrations have jumped 25%. Unaffiliated voters have soared, growing 80%.

Pulling the district across the Chesapeake Bay into Annapolis or Baltimore County could pick up more Democrats, creating “an easily surmountable margin in a decent year for Democrats,” Rubashkin said.

That is, if the court approves the maps.

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The last time Maryland’s districts were redrawn after the 2020 Census, Republicans won a court challenge. A judge called the map an “extreme gerrymander” — a term describing a map manipulated to benefit one party.

After the court ruling, leaders in Annapolis came up with a map with more geographically compact districts that still yielded a 7-1 split among the House members in 2022 and 2024.

Harris’s office did not respond to a request for comment but has said changing the maps “wouldn’t be fair” and warned Democrats he’ll challenge a redrawing of his district.

“Be careful what you wish for because we will take this to court,” Harris told WTOP News in August. “It will go as high as necessary and in the end a judge could draw a map that actually has two or three Republican congressmen if the map is drawn fairly.”

Meanwhile, Day, the father of two school-aged children, isn’t quite convinced this is the moment.

“While the General Assembly considers what our election maps might look like, my responsibility, I think, is to continue to give 110% to the Moore-Miller administration.”