Will Jawando often references “Star Wars” on the campaign trail.

He quotes Obi-Wan Kenobi, who warns, “Only a Sith deals in absolutes.”

That Jedi wisdom, Jawando says, applies to local taxes.

“For example, ‘I’ve never voted to raise taxes. I will never raise taxes,’” he said, alluding to one of his opponent’s campaign promises. “That’s an absolute.”

Jawando, a 43-year-old County Council member and civil rights attorney, has positioned himself as the most progressive candidate in the race for county executive, with policy plans that include raising taxes on the wealthy to expand services like after-school programming and child care options, and maintaining caps on rent increases to protect low-income tenants.

He has cast himself as a fierce advocate for immigrants and an outspoken critic of the Trump administration.

Jawando also brings to his campaign experience from running for five different offices since 2014. He has been knocked for his frequent runs, but at least one of his former critics is now a supporter.

The Democratic primary to succeed term-limited Marc Elrich includes five candidates, but all eyes are on the three council members running — Jawando, Andrew Friedson and Evan Glass. The winner of the June primary is all but assured victory in the November general election, as Democrats outnumber Republicans 4-1.

The candidates’ priorities align in many ways. Ike Leggett, who was county executive from 2006 to 2018, said their plans to make living in Montgomery County more affordable will set them apart.

“I think all three of them are speaking to that,” he said. “The question, I think, will be how do they lay out a particular vision that people can relate to?”

Who is Will Jawando?

At a Democratic breakfast club meeting in February at the Parkway Deli in Silver Spring, Jawando began his remarks by making a plug for the cupcakes sold at the front counter.

His mother has provided Parkway with baked goods for the last 15 years.

He also went to high school 10 minutes down the road, at St. John’s College High School. So the deli has long been a haunt of his.

“Cheeseburger Special was my go-to. Still is — now I just get Beyond Meat, you know, cause I’m older,” he said, to some light chuckles among the few dozen Democratic club members who gathered in the deli about an hour before opening to hear Jawando’s plans.

He began with his family history. His mother was born and raised in Kansas, and his father immigrated to the U.S. after fleeing a civil war in Nigeria. The two met as college students in Kansas.

He grew up in Long Branch, raised by his mother after his parents split. He said his family was low-income and that by eighth grade he had moved five times, as his mother sought an affordable apartment.

Jawando is now a homeowner with eight others — including his wife, four children, a niece and in-laws — living under his roof.

He said his spectrum of living arrangements informs his approach to housing legislation and makes him uniquely qualified to be county executive.

“I’ve experienced the panoply of experiences that happen in Montgomery County,” he said.

As a student at St. John’s, Jawando played basketball and eventually competed at the Division III level at Catholic University. He still plays most Saturday mornings.

“He’s always been the guy who was willing to take the challenge, and get in the paint and, you know, throw some elbows when necessary,” said his former teammate and longtime friend Justin Harrison. “He was the ultimate competitor.”

Jawando garnered attention in his senior year of college for helping to establish a campus NAACP chapter at Catholic. His advocacy pitted him against the university administration and introduced him to influential figures in the area, including U.S. Rep. Kweisi Mfume, who at the time was president of the NAACP. Mfume is now supporting Jawando’s campaign.

The experience also propelled Jawando into government and politics, providing the connections that would land him a law fellowship in U.S. Rep. Nancy Pelosi‘s office.

Lorraine Miller, who led the D.C. branch of the NAACP and whom Pelosi would later appoint as the clerk of the House of Representatives, took notice of Jawando’s work.

“Will had great ideas about how we interact with young people, how we talk to them,” which Miller said was notable “because we were just coming out of the ’80s and the ’90s, where we didn’t speak the language of young people very well as a party.”

Jawando went on to work in the Senate offices of Barack Obama and Sherrod Brown.

He rejoined Obama’s team years later, first working in the White House’s public engagement office and then joining the U.S. Department of Education.

He also worked for Discovery Communications and a D.C.-based consulting firm, started a nonprofit and a job-shadowing program, and had unsuccessful runs for state and federal office before being elected to the County Council in 2018.

Policy plans

Jawando, explaining his agenda to the Parkway Deli crowd, said the next county executive will have a responsibility to stand up to “the hateful rhetoric that we’re seeing at the federal level.”

On the County Council, Jawando has supported several bills to protect immigrants. His stances have garnered him support, including an endorsement from the immigrant advocacy organization CASA In Action.

“We’re in a unique moment in American history where you’re going to have to do things that push the lines of federalism, because we have a cruel government right now,” he said.

He has been particularly outspoken about a measure that, with some exceptions, would prohibit federal, state and local law enforcement officers from wearing masks in Montgomery County.

The bill was recently the subject of a dispute among the normally cordial council.

Jawando introduced the bill in January, but the council — much to Jawando’s displeasure — tabled it while the state legislature considered similar legislation during its 90-day session that ended Monday.

He tried to get his colleagues to fast-track the bill during a meeting in March, and the move sparked a fraught debate in which several of Jawando’s colleagues accused him of creating a divisive moment to benefit his campaign.

Jawando, though, said some members were “gaslighting” him about their support of the bill, and he felt the measure was too urgent to sit on.

“I took this step because I felt there was no other way,” he said during the tense March council meeting.

Jawando has been outspoken about bolstering education spending, too. That advocacy earned him the endorsement of the influential Montgomery County teachers union.

“He has been a consistent supporter of the schools and a champion of educators,” said David Stein, board president for the Montgomery County Education Association.

Jawando also said the county must spend more on government services that can provide support and stability in people’s lives, including after-school programming, child care and reliable transportation.

To boost investment in these areas and others, he believes the county must increase the amount of money it borrows by selling bonds, raise the income tax rate for wealthy earners and require companies to pay higher taxes on commercial properties.

The housing dilemma

Jawando has further distinguished himself with his approach to housing.

Rent stabilization, which limits annual rent increases, is a defining issue in Montgomery County’s local races.

The law has powerful supporters, including Elrich and Council President Natali Fani-González. But in this election cycle, Jawando is its most visible proponent.

Jawando said the law has kept rent increases in check and helped families remain in their homes.

But developers and some officials say rent stabilization, passed in 2023, is stagnating growth and leading potential investors to no longer consider doing business in Montgomery County. At least one of Jawando’s opponents wants to tweak the law.

Potomac-based developer and investor Peter Henry said he’s been keeping a close eye on the candidates’ stances toward several housing policies, including rent stabilization. One candidate has stood out.

“The most worrisome is Will Jawando,” he said.

Jawando, though, points to a $2.8 billion project in White Oak that the council recently approved to argue that rent stabilization isn’t driving away growth.

“We just had one of the largest investments in the county, under rent stabilization,” Jawando said.

The company first contracted with the county in 2023, the same year council members passed rent stabilization. The law states that new housing units won’t be subject to rent stabilization for their first 23 years.

Hans Riemer, a former council member who supported Jawando’s first campaign for office in 2014, said Jawando has changed his approach to housing since entering local politics. Riemer has endorsed Friedson in this race.

“Will was initially in favor of pretty ambitious housing, and then he completely changed and has become, you know, kind of like a Marc Elrich anti-housing person,” Riemer said. “To me, that’s like closing the door on the middle class.”

Jawando, though, said Riemer’s idea of being pro-housing is more aligned with being “pro-developer.”

He said his policies prioritize middle-class housing and protections for renters.

“My job is to strike a better deal,” he said. “We need development. But we need development that is a good deal for taxpayers, that doesn’t displace current residents.”

Running again

Jawando is certainly the most experienced campaigner in the race.

He lost a state delegate race by just 1% in 2014. Two years later, he ran for Congress and received 4.6% of the vote in a primary race won by Jamie Raskin.

He counted victories even when he lost, including prominent endorsements and significant fundraising. Those results, Jawando says, laid the groundwork for future success. But the campaigns brought out some early critics.

Keith Berner wrote a political blog in the 2010s, when Jawando “ran for seemingly everything that had an open spot.”

He said in a recent phone interview that “I had particular sensitivity — I would say I probably still have it — to politicians who strike me as being overly ambitious.“

Berner now counts himself among Jawando’s supporters.

He said he has seen the council member lead on key issues like care for working families and renters, affordable housing and protecting immigrants.

Jawando said winning elected office has never been his motivator.

“It’s always been about, ‘how do I impact the community in a positive way?’ ” he said.

In between races, he founded Our Voices Matter, a social justice organization that is now closed, and Summer R.I.S.E., a summer job-shadowing program for high school juniors and seniors that is now run by the school system.

He scored his first victory in 2018, winning an at-large council seat. He won reelection in 2022.

But then in 2023, when former U.S. Sen. Ben Cardin announced he would retire at the end of his term, Jawando became the first candidate to jump in the race.

His campaign, though, was short-lived. He said he dropped out once he realized he was taking potential votes from then-Prince George’s County Executive Angela Alsobrooks, who went on to win.

What comes next?

Jawando said that if he weren’t in office, he’d consider coaching basketball. He said it’s one of the best ways to help and mentor young people.

He’s coached before, helming the junior varsity team at St. John’s College High School years ago.

Jawando said he’s spent more time thinking about the decisions he would make as county executive than what he would do if he lost. But the thoughts still make their way in.

“If I were not to be successful in this race, I will find another way to be impactful in the community,” he said. “You know, maybe I’ll go be that coach.”

He later mused, “Do I come back to politics at some point? Maybe, but if not, that’s OK too. I don’t have to be in politics.”