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Harford County pursues Penman in court, even as councilman prepares to exit job

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Harford County pursues Penman in court, even as councilman prepares to exit job

Nov 05, 2026 | 5:00 am ET
Harford County pursues Penman in court, even as councilman prepares to exit job
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The term of Harford County Councilmember Aaron Penman (R) ends in a month, but the county is appealing a decision that let Penman, a sheriff's deputy, return to the panel. (File photo by Bryan. P. Sears/Maryland Matters)

Aaron Penman’s days as Harford County councilman are numbered, but that isn’t stopping Harford County Executive Bob Cassilly from trying to reverse the ruling that restored his fellow Republican to the council this year.

The county Wednesday asked the Supreme Court of Maryland to overturn an April ruling by an Appellate Court of Maryland panel that reinstated Penman, almost two years after he was removed by a lower court that said he could not serve on the council while employed as a county sheriff’s deputy.

Harford County Attorney Jefferson Blomquist argued the high court should rule on the issue even though Penman will only be on the court until Dec. 7, when the new council is sworn in. Penman did not run for reelection this year.

“No, it does not become moot because to become moot, it has to be incapable of repetition,” Blomquist said in response to justices’ questions. “Clearly this is not a situation that’s capable of repetition.”

The legal issues, Blomquist said, are of great public importance.

County Charter eligibility provisions “provide for the checks and balances and the separations of power that allow our government to function as a republic or as a democracy,” he said during arguments Wednesday.

But Cassilly, who has feuded with Penman and his boss, Sheriff Jeff Gahler, as well as the outgoing council president, is not relenting in his pursuit of a ruling that is both against the councilman that also might clarify his county’s charter.

Wednesday’s appeal is one of two before the Supreme Court of Maryland involving Penman and potential conflicts between his elected position and day job. The court is set to hold arguments in March on a case involving Penman and the Harford County Ethics Commission.

Cassilly in 2022 refused to swear in Democrat Jacob Bennett to the council, saying the charter banned Bennett because he was also a middle school science teacher.

The state’s highest court ultimately ruled in favor of Bennett, ruling that county charter eligibility provisions were wrongfully applied to Bennett because “a county board of education does not have a particular character as State, county, hybrid, or independent entity.” A school board can have the character of any of those entities — the definition is dependent on the situation, the court wrote.

Cassilly later used the same charter language — and the county ethics commission — to deny Penman a seat on the council. In both the Bennett and Penman cases, the same circuit court judge ruled in Cassilly’s favor.

Penman was off the council for roughly 18 months as he appealed. In April, the Appellate Court of Maryland ruled that while the position of sheriff is a constitutional office, it’s role as a state or county government entity is trickier.

“In the absence of clear textual guidance or definitive legislative history, we must apply the presumption favoring eligibility,” Judge Jeffrey Geller wrote for the panel.

“In this case, a county council member who also serves as a deputy sheriff, and the sheriff who employs them, both ultimately answer to the voters,” Geller wrote. “When statutory text leaves the question open, the ultimate judgment belongs not to this Court, but to the ballot box.”

The court remanded the case back to Harford County Circuit Court, where a new judge specially appointed to the case restored Penman to his job.

In the meantime, because of the initial ruling, Penman opted to not seek re-election, instead backing Alison Imhoff, the social worker who had been appointed to fill his then-vacant seat.

Justin DeMichael, who is one of two attorneys representing Penman, told the high court Wednesday there are similarities between Bennett’s and Penman’s jobs. In both cases, the school system and sheriff’s department are independent agencies and not necessarily within county government.

“I think they are definitely unique in how they are created,” DeMichael argued. “I think if you do an analysis of the sheriff’s office, it creates the same contextual issues that were present in Bennett.”