Jessica Haire: Republican hopes to rein in spending, slow government expansion as Anne Arundel County executive

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Jessica Haire meets and greets Anne Arundel County voters at Greenstreet Gardens in Lothian alongside her daughters Addison and Olivia and her husband Dirk.

In early October, Jessica Haire made a campaign stop at a garden supplies store in Lothian. As she prepared to speak at Greenstreet Gardens, the first-term Republican County Council member felt a pull at her jacket. It was Haire’s 5-year-old daughter, Olivia.

It didn’t matter that Haire was moments away from asking those gathered to give her their vote for county executive in a few weeks. Olivia wanted to show her mom something on her cellphone. Without missing a beat, Haire smiled down at her daughter with a word of validation and the child toddled away with the phone in her hand and a cracker in her mouth. The transition from politician to mom and back was seamless.


“We bring the kids along a lot. All the party activists and Republican elected officials in the county, they all know our kids,” said Haire’s husband, Dirk Haire, who is also the chair of the Maryland Republican Party.

Motherhood permeates all aspects of Haire’s life.

Jessica Haire meets and greets Anne Arundel County voters at Greenstreet Gardens in Lothian alongside her daughters Addison and Olivia and her husband Dirk.

In addition to being a mom of four, the council member from Edgewater views herself as a mom-like figure to the foster children she advocates for in court. She feels similarly about the young residents of Anne Arundel County who are without reliable bus service or lights on their sports fields. It’s her maternal instincts that make her a good listener, negotiator and leader, her friends and family say.

Haire’s “mom friend” Rita Shkullaku, a doctor who practices internal medicine in Anne Arundel County, has two young daughters who play with Haire’s daughters Addison, 7, and Olivia, 5 (She also has two stepchildren, Connor, 18, and Bailey, 22). The moms spend a lot of time together talking about work and family.

“She’s a really good problem solver,” Shkullaku said. “When the kids disagree she’s able to mitigate an argument. She’s very fair with all the kids involved.”

As a lawyer and an engineer, those are skills Haire has been honing for years by helping companies solve expensive security and safety problems and settling disagreements.

“I’m confident that whatever problems come up in any aspect I’m dedicated and hardworking and I will find a solution,” Haire said in a recent interview with The Capital.

That kind of diplomacy has been critical to Haire’s work on the County Council over the past four years representing District 7, which covers south county including her neighborhood of Edgewater. As one of three Republicans on the council with a four-member Democratic majority, every piece of legislation Haire has passed has required bipartisan support, such as a bill she sponsored to ease business restrictions for owners of plant shops and nurseries, and another that removed a fee tacked onto a property tax credit for public safety workers. A bill she introduced to raise the county’s rainy day fund cap in 2021 received unanimous support on the council.

The 39-year-old will need to appeal to a wide swath of county residents to defeat incumbent Democratic County Executive Steuart Pittman in the Nov. 8 midterm general election. But she’s confident that her message of wiser spending, lower taxes and slower growth of county government is resonating with voters who have struggled financially to keep up with the demands of Pittman’s expansion of county government and budget — he raised taxes during his first year in office — while recovering from the pandemic.

“I think one of the motivating things for her is that ultimately how effective she is is what’s going to ultimately bring change for children and for education and for infrastructure and for the community,” Shkullaku said. “She recognizes that direct connect from the community to, ‘If I can make this happen this will be better for my kids.’”

Jessica Haire meets and greets Anne Arundel County voters at Greenstreet Gardens in Lothian alongside her daughters Addison and Olivia and her husband Dirk.

“She makes 24 hours in a day look like longer”

Haire was born on Pease Air Force Base in Portsmouth, New Hampshire (now known as Pease Air National Guard Base) in 1983. Her mom, Carol, was in the military. She’s the middle child of five kids — Alan, Karen, Amanda and Rebecca.

It was a fun experience for Haire who particularly liked tagging along with her mom, a doctor in the Air Force, to work the medical tents at air shows.

“I really wanted to be an astronaut or a fighter pilot or something like that when I grew up,” Haire said.

Haire’s sister, Karen Durbin, described her as an adventurous and curious child who wanted to experience everything.

“There’s nothing she wouldn’t try, nothing she didn’t want to know about,” Durbin said.

She’s the family member each sibling and parent would say they are closest to, Durbin said. Even as a child she was intuitive and caring, Durbin said.


To afford the cost of raising five children, Carol Vasconcellos worked multiple jobs and brought the kids around to work, including at a night clinic. Though Haire’s mom worked in Portsmouth, the family lived in Massachusetts.

“She’d bring two things with her; she brought crayons and sleeping bags,” Haire said. She and her sister Amanda would play in an exam room together every Wednesday night, removing the paper sheet from the exam table and drawing on it with the crayons.

Carol Vasconcellos was eventually able to open her own medical practice. Her mother’s example taught Haire that hard work pays off, the value of generosity, and it instilled in her a sense of patriotism, believing anything is possible in the United States for people who set their minds to their goals.

Her father, Alan, was a teacher who became dean of the engineering school at the University of Hartford. His work in math and science academia piqued Haire’s interest in being an engineer herself.

Haire’s decision to go into engineering didn’t surprise Durbin, who said her sister was a born problem solver.

“The second someone has a problem she’s like, ‘OK what are we going to do?’” Durbin said. “It doesn’t matter if she has to drive 10 hours in one day to fix something. There are so many stories.”


After graduating from Winsor School in Boston, a private, college-preparatory day school for girls, she studied civil engineering at George Washington University in Washington D.C. The District felt like “the center of the world,” at that time in her life, said Haire, who often studied at the Library of Congress, because it was where big things were happening.

After briefly considering a business degree, she chose engineering after a high school guidance counselor told her to study whatever she loved to do when she was 10, which, for Haire, was building structures with Lincoln logs and Legos. Her structures would take up half the house, Durbin said.

“When you study engineering, really what you’re studying is problem-solving,” she said. “You take any issue and you take a set of constraints, could be budgetary, could be time, could be space constraints, whatever it might be, but you work at it. You pull all the different levers that you have until you find a common sense, innovative, efficient solution,” she said.

Upon graduating in 2005 she worked doing sanitary sewer design for Urban Engineering and Associates. But she soon missed her family and decided to return to New England where she went to work in airport design for New Hampshire-based Gale Associates.

There she led a project at Manchester Airport to fix a giant culvert that snaked from the airport, under a road, and beyond the airport’s perimeter, presenting a security problem as people could walk right through the culvert if there was no water in it. Haire designed a structure of beams and grating that prevented people from coming through but allowed in small critters and water. It was Haire’s favorite engineering project, she said.

“It was very exciting. I still love it. I have pictures somewhere,” she said.


Around this time, Haire’s parents were going through a divorce. Her mom decided to leave medicine and become a lawyer. She asked if Haire would take the LSATs with her. Haire, who loved game theory and the problem-solving section on the test, said yes.

In 2008, Haire returned to D.C. to pursue a law degree and master’s degree in international studies simultaneously at American University. During and after her schooling she worked at the Smith Currie and Hancock law firm, which was acquired by Fox Rothschild about a week after she started working there full time. She did government contracts work on infrastructure projects there until 2019.

Her friends and family say she has an incredible work ethic and manages to juggle her work as a lawyer, as a council member, as a mother, a wife, a friend and a court-appointed special advocate without seeming to break a sweat.

“I try to do what she does,” Shkullaku said. “She makes 24 hours in a day look like longer.”

“The woman needs no sleep. She never has,” Durbin added. “As a kid she didn’t nap. She was up.”

After a brief first marriage, Haire met Dirk Haire while they both worked at Fox Rothschild. The pair married and moved in together in Edgewater in 2014.


In 2017, Haire started volunteering as a court-appointed special advocate for kids in foster care in Anne Arundel County, getting to know children navigating the foster system. It was a minimum one-year commitment but Haire continues it to this day.

“I thought maybe I’m here for a reason”

Though Haire had been volunteering with the Maryland Republican Party since 2010, according to Dirk Haire, she started to get more involved when Larry Hogan was running for governor in 2014. She liked the Republican’s focus on lowering taxes and limiting government.

“I got to know a lot of the folks involved and really just kind of enjoyed it and then started to see so much of my career, what I had worked toward, playing out at local levels,” she said. Politics combined aspects of her engineering, legal and international studies experience.

Dirk Haire said he wasn’t surprised to see her get increasingly interested in politics with her passion for public service and competitive spirit.

She came to realize nobody on the County Council had an engineering background. With so many infrastructure and development planning issues popping up in the county, she started to hear peers voice their desire for an engineer on the council.

“I thought maybe I’m here for a reason,” she said. “Maybe this is where I’m supposed to be. I would love to help people with this kind of work. ... Sort of overnight I said I want to try this and then it was off to the races.”

Jessica Haire meets and greets Anne Arundel County voters at Greenstreet Gardens in Lothian alongside her daughters Addison and Olivia and her husband Dirk.

Haire defeated Jonathan Boniface in the Republican primary in 2018. She then went on to defeat Democrat James Kitchin, who is now Pittman’s director of community engagement and constituent services, in the general election.

Tracey Lane, an Annapolis resident, who serves as Haire’s special advocate supervisor, said she was surprised to hear Haire was running because she didn’t know it was something she was interested in.

However, she wasn’t at all surprised she won.

“She can be tenacious. Anything that she feels like she’s going to take on, she’s going to take it on completely,” Lane said.

During her first term, Haire has sponsored bills to remove regulatory hurdles for small businesses, provide property tax credits to service-disabled veterans and help constituents resolve flooding issues. But with her successes have come disappointments as well, including a bill she sponsored to allow landlords to provide discounts to public safety officers. It failed on a party-line vote.

“I was sad about that because I felt like it was something we were doing to help with cost of living for our local workforce,” she said.


“She doesn’t usually just say things, she does them also”

Ever the practical lawyer, Haire wasn’t sure what to do as her first term on the council was coming to an end. She could run for reelection, for county executive or for another office. In March 2021, after she formed an exploratory committee, she found there was interest in her running for the county’s top office.

Residents responded to her promises to eliminate chronically vacant positions the county continues to fund, something for which she advocated during the most recent budget cycle but failed to achieve when she couldn’t gain majority support on the council.

To get on the November ballot, Haire needed to defeat a formidable foe in former Annapolis Del. Herb McMillan in the July primary. McMillan aligned himself closely with former president Donald Trump throughout the campaign and criticized Haire for taking tens of thousands of dollars in campaign contributions from a Silver Spring developer hoping to build a rubble landfill in Odenton.

Through the grueling primary campaign, Haire handled the criticism well, Shkullaku said.

“I can remember a couple of times where people have written on social media pretty insulting types of things or even said things to her and she’s always graceful in response, understanding that everyone comes from their own experiences and everyone may not agree with her,” she said.

But voters remained supportive. She won 44% of the vote in the July 19 primary, beating McMillan by more than 2,000 votes. She picked up victories from not just her home district in south county but from six of the county’s seven council districts. McMillan only outperformed her in his home region, the Annapolis peninsula.


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At the Greenstreet Gardens event, she reiterated her message — bolstering the county’s literacy and numeracy rates, reducing crime and cutting taxes.

Supporters of Haire and other Republican candidates for local and state offices came to Lothian from all over the county to raise concerns and show their support, including Heather Berlett, president of the Republican Women of Anne Arundel County. Berlett sees Haire as the candidate who will run a more wisely governed county.

“Jessica Haire does stand for financial responsibility in our county,” Berlett said.

Jessica Haire meets and greets Anne Arundel County voters at Greenstreet Gardens in Lothian alongside her daughters Addison and Olivia and her husband Dirk.

Ray and Stacy Greenstreet, who hosted the event, said they wanted to give people a chance to know their local candidates, particularly those who like Haire have been so supportive of agriculture. When she learned greenhouses were having a problem growing and shipping plants because of provisions in the county code, Haire passed legislation this summer to update the code to match current industry practices.

“Anne Arundel County is still an agricultural county,” said Ray Greenstreet. “We need people who support us and take care of agriculture and all the different facets of agriculture.”

Haire’s husband and friends know she’s capable of preparing the county for any hardship to come and will be able to get the government growing at a slower and steadier pace.


“She doesn’t usually just say things, she does them also,” Shkullaku said. “She cares about how the people around her feel and what they have access to.”