Wright Hits The Road, Lierman Hits Short-Term Rentals, Freedom Caucus Hits Back, More Notes

By Bryan P. Sears and William J. Ford, Maryland Matters

August 20, 2025

There are many signs of the end of summer in Maryland, and when State Superintendent Carey Wright starts making the rounds of counties to visit schools, it’s a good sign that summer is ending and the school year is starting.

Wright plans to be in Frederick County early Wednesday to see the smiling faces of teachers, faculty — maybe even smiling students — when schools there open for the 2o25-26 academic year. Frederick is one of the first two counties to return tomorrow, along with St. Mary’s County.

Joining Wright will be Frederick County Public Schools Superintendent Cheryl Dyson, the system’s first Black superintendent, now entering her fourth year in the job. Dyson recently received a national award for her work.

Next Monday, Wright is scheduled to visit Baltimore County, one of nine school systems opening on Aug. 25. They will be followed by Calvert, Montgomery and Prince George’s counties on Aug. 25 and Allegany County on Aug. 27. The remaining nine school systems are set to open Sept. 2, the day after Labor Day, according to a state Department of Education calendar.

If it’s any consolation to the kids in Frederick and St. Mary’s counties, the calendar shows that they’re scheduled to be among the first to get out of school next June.

Further information on Wright’s first-day travels was not available as of Monday afternoon.

Lierman scraping for short-term rental scofflaws

Maryland Comptroller Brooke Lierman is looking at short-term rentals in the state.

The effort by the state’s top tax collector has less to do with finding a unique or fun place to stay on vacation and more to do with ensuring that anyone renting out properties in the state is reporting everything on their taxes.

Comptroller Brooke Lierman (D) said her agency is scraping public data on short-term rental properties in Maryland to ensure each owner “pays their fair share.” (Photo by Bryan P. Sears/Maryland Matters.)

This year, the General Assembly passed legislation to centralize the collection of taxes on short-term rentals — think platforms such as Vrbo and Airbnb. Coupled with that are new regulations that have yet to be implemented. Lierman said her agency is already looking at the state’s new law and similar legislation in other states.

“There are probably a couple cleanup things that we’d like to do this year that we’ll talk with the sponsors about, but we care very much about making sure that everybody pays their fair share, and then it gets back to you,” Lierman told the audience at the Maryland Association of Counties meeting last week. “So that will be our central driving force — to make sure that all the taxes are collected and that they are remitted to the appropriate place, and that we’re accounting for that along the way.”

Tangential to that effort, Lierman told the gathering of county officials in Ocean City that her office is now seeking rental owners who may not accurately report their rental income.

Lierman told attendees at the MACo summer conference Saturday that her office has hired a consultant to “scrape publicly available data through Vrbo and Airbnb.”

The data collection is part of an effort to “look at what folks are making and work and then compare that to what they’re reporting their income to us,” Lierman said.

The comptroller said she believes the data collection is the first of its kind in the country.

“So, if I see that you have 10 Ocean City rentals that are rented at $500 a night, nine months of the year. And I don’t see that on your tax return, right?” Lierman said.

‘We told you so’

Members of the legislature’s hard right Freedom Caucus are taking a victory lap after a federal appeals court last week struck down a portion of the state’s digital ad tax.

“The court confirmed what we said from day one: this tax is unconstitutional, reckless, and destined to fail,” said Del. Matt Morgan (R- St. Mary’s), chair of the seven-member group. “Instead of strengthening Maryland’s economy, the Democrat supermajority pushed through a radical scheme to shake down tech companies only to waste millions of taxpayer dollars defending a law that was doomed in the courts.”

The caucus, in letters to Comptroller Brooke Lierman and Attorney General Anthony Brown, both Democrats, demanded to know how much money the state has collected on the tax thus far and how much has been spent defending the law in court.

The Maryland House Freedom Caucus. File photo by Bryan P. Sears/Maryland Matters.

The 2021 law — the first of its kind in the nation — imposes taxes on large tech companies such as Amazon, Apple and Meta for the digital ads they sell within the state. The law was projected to raise $250 million that would be used to pay for the state’s Blueprint for Maryland’s Future education reform efforts.

But the law faces several legal challenges.

On Friday, the 4th U.S. Circuit Court of Appeals issued declared one portion of the law unconstitutional. The three-judge panel found that a provision of the law barring companies from itemizing the cost of the tax on invoices to customers violates the First Amendment.

The court compared the law to Colonial-era tax revolts and said preventing a company from telling customers about the tax is a free-speech violation.

“No doubt, Maryland has prudential reasons not to want the question answered. But as all we have said so far should make clear, keeping out of hot water with voters is not among the interests that can justify a speech ban,” the court said in its decision.

The ruling does not overturn that tax. The appellate judges merely remanded the case back to U.S. District Court in Maryland where a judge will determine an appropriate remedy. Even so, members of the caucus were quick to taunt Democrats.

“We told you so,” the caucus statement concludes.

Lierman anxious to resolve digital ad tax challenges

Republicans are not the only ones watching the various legal challenges to the ad tax and awaiting a final decision.

Comptroller Brooke Lierman, the state’s top tax collector and an attorney, told Maryland Matters Saturday she had not had an opportunity to review the appeals court decision issued the night before fully.

“I do not think it affects the larger part of the law,” she said, referring to whether or not the state can legally impose the tax.

There are several related legal challenges, including one in tax court that could — once all the appeals are exhausted — determine whether the 2021 law stands.

Included in those is a challenge in the Maryland Tax Court. “We’re awaiting the tax court’s decision,” Lierman said.

When that decision will come remains an open question.

“We do not know. I wish we did. We’ve been waiting for a while,” said Lierman.

Elliott leaves second floor for campaign trail

More change is coming to the second floor of the State House.

Carter Elliott IV, senior press secretary to Gov. Wes Moore (D), announced his departure in an email to reporters Tuesday. The announcement came a day after Fagan Harris, Moore’s chief of staff, announced he has accepted an offer to become the new president and CEO of the Baltimore-based Abell Foundation.

Carter Elliott IV, a spokesperson for Gov. Wes Moore (D), prepares for a State House press conference. (File photo by Danielle E. Gaines/Maryland Matters.)

“As my last day in the Governor’s Office comes to a close I just want to reach out to say it was the greatest pleasure of my life to serve in this role and I’m grateful to have gotten to know some incredible people,” Elliott wrote in his brief goodbye note.

“I grew up in a family where the best career that you could follow was being a farmer, a teacher, or a public servant—this had been my dream for as long as I can remember,” added Elliott, who came to Maryland from Virginia.

Elliott has served nearly three years in Moore’s communications shop. Prior to his state service, he spent seven months with Moore’s first statewide political campaign in 2022.

Elliott described his time in the Moore administration as “a hell of a ride.”

But it’s not the end of the trail for Elliott who leaves his government role to join Moore’s reelection campaign.