At an airy catering hall overlooking the Severn River on a pleasant night late last month, the promise and peril for Anne Arundel County Republicans this election cycle was on vivid display.
Inside, County Councilmember Jessica Haire (R), a candidate for county executive and a rising star in the state GOP, was being feted at a cocktail party.
“She’s a great person. Super smart,” said John Thibodeau, who owns an insurance business in Annapolis.
But outside, in the parking lot, a handful of Haire aides and supporters were nervously eyeing a nearby hillside and the traffic passing along Riva Road. There had been rumors in Anne Arundel Republican circles that day that a conservative group — possibly affiliated with one of Haire’s GOP primary opponents, former state Del. Herbert McMillan, and still aggrieved over COVID-19 restrictions imposed by the county government earlier in the pandemic — would be there protesting.
But a protest never materialized — and an adviser to McMillan later denied that the candidate was part of any discussion about disrupting Haire’s fundraising event. Still, Haire couldn’t resist a dig.
“This is how effective my opponent is,” she told her audience at the fundraiser. “No one showed up.”
The election for Anne Arundel County executive is one of the most compelling in the state this year. In addition to determining who will run one of Maryland’s most populous and changing jurisdictions over the next four years, the result may also say a lot about political trends nationally and in the state.
Anne Arundel epitomized the blue wave that swept across suburban America during the Trump era, and some communities in the county are becoming demonstrably more Democratic. But there remain solid pockets of conservatism and swing voters.
Republicans and many Democrats believe County Executive Steuart Pittman (D) is vulnerable this fall. Plenty of political professionals, especially on the GOP side, see him as an accidental executive, who profited from strong national Democratic tailwinds in 2018 and an unpopular Republican incumbent, Steve Schuh.
But some Democrats believe Pittman is vastly underestimated and has now amassed a record in office that while undeniably progressive, has aligned with residents’ priorities on growth and development and largely amounts to promises kept.
“Steuart Pittman has led Anne Arundel County well through unprecedented challenges and made remarkable and substantial progress through his first term, creating economic opportunity for the county’s residents, implementing smart growth policies, and protecting the environment,” said Brian Doory, a seasoned Democratic strategist who is managing director of Scarlet Oak Strategies, a corporate and public affairs firm in Annapolis.
Republicans would love to bounce Pittman from office. But first, they’ve got to get through a messy primary and hope the party can unify when it’s all over two weeks from now.
“That’s certainly my intent,” Haire said in an interview.
But that may be easier said than done.
There are five Republican contenders, but the primary is widely seen as a two-way race between Haire, who is finishing her first term on the county council, and McMillan, who spent a dozen nonconsecutive years representing the Annapolis area in the House of Delegates.
Haire and McMillan, it’s fair to say, do not like each other.
The temptation is to compare the race to the Republican primary for governor, with Haire in the role of the establishment favorite, former state Commerce Secretary Kelly Schulz, and McMillan the renegade like Del. Dan Cox (R-Frederick).
“It looks to me like the McMillan people tend to be Cox voters and that the Haire voters are probably Schulz voters,” said Paul Ellington, former executive director of the Maryland Republican Party, who isn’t working for either candidate. “Herb has definitely positioned himself as the outsider.”
Certainly Haire, in her short political career, has benefited from her connections — chief among them her husband, Maryland Republican Party Chair Dirk Haire, who has made his wife’s career his top priority despite multiple political obligations. And she’s now the choice of many Republican elected officials in Anne Arundel and beyond, and has the endorsement of influential groups like the Anne Arundel Association of Realtors.
But Haire is no slouch on the professional or policy front. She began her career as a civil engineer, and later got a law degree.
“Local government is literally where the rubber meets the road,” she said. “And what is engineering? It’s literally problem solving.”
Haire also offers a full-throated critique of Pittman’s tenure. In her view, the county has spent too much under Pittman, with very little to show for it.
“Does anyone now feel they’re better off than they were when Pittman took office?” she asked.
Last month, when the county council approved Pittman’s annual budget on a 6-1 vote, Haire was the lone dissenting vote. The council’s two other Republican members supported it.
Haire argues that she has been an effective councilmember on a variety of fronts, even while serving in the minority.
McMillan did not respond to phone and email messages seeking comment for this story. Throughout his political career, he has touted his fiscal conservatism. His longtime campaign slogan has been, “It’s your money.”
On his campaign website, McMillan pledges to hold the line on taxes and cut wasteful spending, and vows to fight for more federal and state funding for important county projects.
“The great people of Anne Arundel County continue to come to me with their concerns about the rising taxes and fees, our school board/school curriculum and mental health of our kids, the rapidly rising crime in their neighborhoods and more,” McMillan wrote recently on Facebook. “I am listening and hear your concerns. I want you all to know that have the knowledge, experience, grit, passion and determination to improve and correct these problems as well as many others. Together we will make Anne Arundel County the best county in Maryland.”
McMillan has also been sharply critical of Anne Arundel County’s COVID-19 health protocols, and while Haire has questioned some of the policies emanating from Pittman’s Health Department in recent months, McMillan clearly has an advantage with conservatives who have been most vocal about restrictions on businesses, schools and personal movement during the worst of the pandemic. On his website, McMillan says “county government under Steuart Pittman has become oppressive and inept.”
Haire also did not endear herself to some conservatives when she supported a resolution in the county council condemning the Jan. 6 insurrection at the U.S. Capitol.
Sometime between the recent mass shootings in Buffalo, N.Y., and Uvalde, Texas, Haire sent a mailer to Republican voters on gun rights showing her shooting a rifle. That brought swift criticism from Pittman and other Democrats.
Haire said Pittman, who is a horse farmer and outdoorsman, is being disingenuous.
“He’s got weapons,” she said. “He knows what I’m shooting there in that photo. I’m shooting clay.”
Haire adds, “I would never use the deaths of children for political purposes.”
Some Democrats have also criticized Haire for working with the Republican consultant Rory McShane, whose political consulting firm has been associated with the group The Proud Boys. Haire said she ended her association with the strategist as soon as she learned of this connection to the extremist group.
Many operatives in both parties suggest that Haire, the mother of two young children, is more relatable to the average voter and would be a stronger general election candidate than McMillan. But McMillan’s fans point out that he is a Naval Academy graduate with deep ties to the county and prospered politically in an area that has grown more blue over the years, regularly giving the late House Speaker Michael Busch (D), with whom he shared a district, fits.
“Whoever comes out of the Republican primary is favored to win in the general, in my opinion,” said Ellington, the GOP consultant.
Haire reported $600,427 in her campaign war chest as of June 7, a total buttressed by a $500,000 loan she made to her campaign in January. McMillan reported $185,692 on hand as of June 7.
Haire’s campaign is being aided by an independent political action committee that appears to be run by national Republican strategists, a possible benefit of her husband’s GOP connections. The treasurer of the entity, Anne Arundel Forward Inc., is Lisa Lisker, a national Republican strategist with ties to U.S. Senate Minority Leader Mitch McConnell (R-Ky.) and was treasurer for Florida Sen. Marco Rubio’s 2016 White House bid. Through early June, the PAC reported spending $18,000 on mailers attacking McMillan.
The mailers, among other things, accused McMillan of being responsible for higher gas prices in the state and for being a “never Trumper,” citing his initial support for then-Ohio Gov. John Kasich in the 2016 Republican presidential primary.
McMillan has upped the rhetoric against Haire in recent days, slamming her on Facebook last week for representing the producer of pornographic movies in her legal practice in the past.
“Councilwoman Jessica Haire campaigned on cutting property taxes 3% but failed to get it done in 4 years,” he wrote. “Instead, YOUR property taxes went UP. Why? Because while serving as Councilwoman, attorney Jessica Haire was too busy representing one of America’s largest porn companies.”
The Facebook post links to two legal documents involving the company Haire represented — both of which were dated before she took office in December 2018.
Three other Republicans are running for county executive: former County Councilmember John Grasso, and two political newcomers, business consultant Chris Jahn and Fernando Berra III, who calls himself a strict constitutionalist. McMillan has taken to hitting Grasso lately for votes he took on the county council, suggesting he believes Grasso could draw votes from his column.
In an interview, Jahn said he thinks Republican voters are looking for something different this time.
“Of course I think I have a chance to win,” he said. “The general public is tired of politics and politicians.”
Pittman: 2018 coalition ‘is still pretty strong’
Meanwhile, in a recent interview, Pittman said the approaching primary — he is running unopposed for the Democratic nomination — is prompting voters to focus on what’s at stake in this election.
“It’s getting closer, so people are starting to think about what we’ve gained and what we can lose if we don’t win,” he said.
Pittman believes he has compiled a strong record that will appeal to many general election voters, not just on growth and development issues, which helped propel him to victory four years ago, but also on matters like the environment, affordable housing, and gun safety. He predicted that his winning coalition from four years ago — “environmentalists, civic groups, teachers, police officers, firefighters, is still pretty strong.”
Pittman concedes that national issues — including abortion, immigration, gun rights and COVID-19 protocols — could become a factor in his reelection.
“If people blame Democrats and Pittman for inflation, then we have a problem,” he said.
But Pittman said he takes solace in the reelection victory last year of Annapolis Mayor Gavin Buckley, a Democrat who overcame national trends to rack up a big margin.
“When it comes to local institutions, voters want services delivered well, and I think we’re meeting those goals,” he said. “Hopefully that insulates us from messages about the economy. Our economy has largely been insulated from the national economy.”
Through June 7, Pittman had $554,452 in his campaign account — not an overwhelming amount for a vulnerable incumbent. But the incumbent said he’s “mobilizing our ground game.”
“We could well be outspent,” he said. “We’ll never raise the amount of money that the Haires can put in.”
Pittman could also be the beneficiary of an independent expenditure campaign. A new organization called Future Anne Arundel has formed to boost his candidacy. Annapolis Alderman Brooks Schandelmeier (D) is the chair of the PAC, and Monica Alvarado, who owns a cafe in the Eastport neighborhood of Annapolis, is the treasurer.
The PAC has yet to report raising money. The Annapolis firm Scarlet Oak Strategies, which is headed by seasoned Democratic operative Raymond Glendening, is advising the PAC.
“We spend most of our time working with nonprofit and corporate clients across the country but every election cycle we try to do a small number of projects to support campaigns we feel strongly about and we are really excited to help Steuart,” Glendening said.