Healdsburg enlists former Army captain to help boost affordable housing units, reduce homelessness

As Stephen Sotomayor races from one workday commitment to the next, he tries to recall his military training, and a mentor’s words about how haste and getting caught up in the heat of a moment can lead to flawed decisions.

Healdsburg’s new housing administrator traded in his Army uniform more than a decade ago for civilian work clothes - a light gray suit with a crisp blue, open-collared shirt on a midweek morning last week. But the guidance offered years ago by a commanding general just before Sotomayor’s deployment to Iraq with the 1st Armored Division remains with him today.

“He told his junior officers, ‘Do not rush into failure. You’re going to be in a time where there’s a lot of pressure coming on you,’?” Sotomayor said, recalling the advice of Gen. Martin Dempsey, who went on to become a four-star general and later served four years as chairman of the Joint Chiefs of Staff under President Obama. “You’ve got to filter out the noise and look at the heart of the issue. To take a step back and make sure you get there.”

In Iraq, Sotomayor, who left the Army as a captain, served a 15-month tour in the early days of Saddam Hussein’s overthrow.

Now 40, the Los Angeles County native is digging into his demanding job as Healdsburg’s housing chief, responsible for preserving the Wine Country city’s dwindling number of available affordable units and building more for its current and future workforce.

Aside from the military, he brings to the post past experience in the public and private sectors, including housing positions that took him to Fresno and back to Los Angeles, managing larger budgets and developing policies around the challenge of homelessness.

His new job is in a much smaller city, in a one-man department. But it comes with great expectations.

In recent years, skyrocketing rents and vacancy rates hovering near zero have sucked up much of Sonoma County’s most affordable housing. Home prices for many families remain out of reach. In Healdsburg, where the median household income is about $63,000, the median home sale price is the highest in the county at $804,000, according to the Sonoma County Economic Development Board.

In more than a few instances, landlords also seeking to cash in on the market have moved to retrofit investment properties, displacing current tenants from their below-market units and hiking rents beyond what they can afford. In the past four years, two high-profile cases involved largely Latino families losing their longtime housing and housing advocates turning out in droves to demand the Healdsburg City Council act on their behalf.

Also, by voter approval in 2000, new housing construction in the city has been limited to 30 market-rate homes each year in Healdsburg, home to about 12,000 people. Affordable units are exempt from the growth restriction, and the passage of a ballot measure in 2018 could help loosen it even further, by allowing another 50 more apartments a year, targeting families of four making an annual income of up to $134,000.

Still, city officials and low-income housing advocates worry the housing gap could push out workers who act as the backbone of Healdsburg’s main economic drivers - tourism and the wine industry. If not addressed in an expedited manner, the shortage stands to thin out the rest of the workforce, affecting school enrollment and other civic mainstays.

“Housing can be generally frustrating because of the timelines it takes to implement,” said Sotomayor. “It takes time and it takes a lot of money.”

Man in the middle

The job he stepped into in January sat vacant for almost a year and a half after the departure of his predecessor, Karen Massey. Almost immediately after becoming housing chief, Sotomayor was asked to wade into a contentious debate that pitted landlords against low-income housing advocates. In February, the City Council directed him to create a charge on landlords to cover relocation expenses for tenants evicted without cause, which would be a first in the county.

At the council’s next meeting in March, the proposal faced a backlash from real estate agents and local landlords and failed to garner enough votes from its five council members. It may return in the months ahead, and Sotomayor, as its principal author, is tasked with finding a compromise between the competing interests. Landlords remain strongly opposed to the concept, but housing advocates have said it is critical to ensuring displaced residents can find suitable housing elsewhere in the city.

“Naturally you want to think of it like, ‘Oh man, what (more) could I have done?’ but in reality-, it’s going to be a positive thing to be able to take more time and look at this,” said Sotomayor. He added that the council’s rejection of the proposal - it had three supporters but lacked the fourth vote needed to pass on an urgent timeline - was the first time in his decade-plus working in housing that he’d experienced such a setback.

“This is our opportunity to really find an adequate balance between tenant and owner. Really, it’s about driving this vision that’s been set forth by the community … to take that vision and implement it.”

Already, a host of key housing items have come before the City Council during Sotomayor’s tenure. More are on the way, including moves to encourage development of granny units by easing rules and reducing fees, strengthen the city’s housing requirements for future hotel and market-rate housing projects and potential purchase of a 23-unit apartment building off Prentice Drive for $5 million.

“There are so many things people want yesterday,” said David Mickaelian, Healdsburg’s city manager. “We have to remind community members this is a marathon, it’s not a sprint. We need to make sure whomever comes into the position, that they’re given an opportunity to be successful.”

Sotomayor’s position is paid for by a 2016 voter-approved tax on hotel stays meant to spur affordable housing development. The city came under fire from residents in February after the latest spending figures for Measure S showed that nearly a third of the fund projected through fiscal year 2020 - $756,936 of $2.6 million - will have been spent on salaries and overhead for city staff. This year, Sotomayor’s annual salary is $110,743 plus benefits valued at $32,933.

Since the tax went into effect, the city has spent nearly $269,000 on programs to preserve affordable units - the same amount as on staff wages and benefits - from the Measure S fund, according to city data.

Mickaelian acknowledged that voter expectations of the hotel tax and scrutiny over how it’s spent are likely to be primary concerns of Sotomayor’s job.

“People want access in this community to that position, to talk about ideas and what their thoughts are,” said Mickaelian. “To have someone like Stephen, who is receptive and willing to meet and address their concerns, is critical. We’re fortunate because that’s part of what his makeup is.”

Sotomayor, who grew up in Glendale, followed in his parents’ footsteps, graduating from the University of Arizona, where he studied history.

Roots in journalism

His father, Frank Sotomayor, is a Pulitzer Prize-winning journalist and former metro editor at the Los Angeles Times. His mother, Meri Sotomayor, worked at the Chicago Tribune as a reporter before staying home to raise him and his older sister.

Stephen, inspired by biographies of the famed American generals George Patton and Douglas MacArthur, and perhaps by G.I. Joe cartoons growing up, opted to pursue his own path into the military by joining ROTC.

“There was just something about that American history - there was a lore to it,” he said. “I thought that was a way to open all these different doors to go places that other people hadn’t been to explore those kinds of things.”

Sotomayor credits his eight years in the Army - including posting in Wiesbaden, Germany between his deployment to Iraq - for helping develop his curious nature, work ethic and ability to lead. The military throws together a diverse set of people who must focus as a group to carry out their mission, he said. As a lieutenant in Iraq, Sotomayor led a company of 180 soldiers in action around Baghdad, leading his superiors to recommend him for a Bronze Star for heroic service.

In Healdsburg, his unassuming manner, youthful energy and frequent smile, framed by a graying beard, have helped him to win early endorsement from some community members and those in the housing field.

His experience in the world of housing - he was previously a homelessness policy analyst in LA and an affordable housing project manager in Fresno - has convinced some of those supporters that he was a smart hire.

“He has a very clear understanding of barriers to housing for people of extremely low incomes and has pretty creative ideas around that and shown real interest,” said Colleen Carmichael, executive director of the area nonprofit Reach for Home, which works with the city to manage and house its homeless population.

“He already knows how to overcome objections, which is key for us, and has credibility coming from LA, meaning you can’t just dismiss him. He understands on a large scale and how to apply that to north county.”

After leaving active military duty, Sotomayor went to work for a private home builder in the Central Valley before shifting his focus to affordable housing with the city of Fresno.

He said he hoped to help people achieve the American Dream of home ownership, while also aiding veterans as they transition back to civilian life.

Sotomayor said he remains passionate about helping those who experience homelessness, particularly in light of how often veterans run the risk as they struggle to reintegrate into society after their years of service. He knows from personal experience the pitfalls of returning from a war zone.

“Imagine every day you’re really focused in on making sure that everybody’s alive, and then you come home and people are arguing over: is there enough parking on the street?” he said between sips of a large latte near Healdsburg’s downtown Plaza. “They complain about waiting in line. You start not to identify with that experience.”

Part of Sotomayor’s plan is to incorporate veterans-specific housing vouchers and ensure those around the community without consistent shelter get their names on waiting lists for both low-income units and the U.S. Department of Housing and Urban Development rent subsidy program. He also aims to reframe the discussion on homelessness - by challenging tropes about people pulling themselves up by their own bootstraps out of economic struggle and instead offering safety nets whenever individuals are ready for them.

“I’ve yet to figure out what a bootstrap is, and I don’t know how you pull yourself off the ground with them,” said Sotomayor. “There’s plenty of people who are a check engine light away from being on the street. So I don’t see affordable housing and homelessness as two separate issues necessarily - I see them as two different approaches” to the same problem.

‘Housing First’

Sotomayor’s approach to homelessness favors the state’s leading “Housing First” model, which attempts to provide a safe place to live before providing other services. The strategy does not require recipients to immediately tackle such problems as substance abuse before accepting help.

That philosophy has its detractors, Sotomayor said, including some in Healdsburg who have questioned why their tax dollars would go toward such programs. On the end of the spectrum are residents who wonder why the city isn’t more proactive in offering services before the housing is built.

Gail Jonas, a 52-year Healdsburg resident and vocal community advocate for the homeless, has continued to prod the city to do more for those in need of shelter. The city is years away from having the transitional units necessary to house homeless residents, so Jonas has called for the creation of a temporary, legal encampment where homeless can stay and feel secure.

Sotomayor for his part said he is open to the concept of an encampment, but would need to study it further. Meanwhile, law enforcement in cities across the county, including Santa Rosa and Healdsburg, have made aggressive efforts to clear and ban unsanctioned encampments.

Jonas has lauded Sotomayor’s focus on mental health services for the homeless in the interim, but contends that such help can be ineffective without first stabilizing someone’s living situation.

“He’s a really good human being with good intentions, but … Stephen’s marching along with everybody else,” said Jonas, a retired attorney. “‘Housing First’ as I interpret it is not meant to mean do nothing for them until they get housing. I realize he’s just a cog in this wheel, but if he spoke up he would make an incredible influence.”

Next steps

Sotomayor indicated that while ideas from residents and nonprofits are welcome, they may not always align with what’s best for the city, or what he must do as the person charged with overseeing its housing finances and in taking direction from Healdsburg’s council.

For now, he said his priorities in the comings months include the community’s larger housing goals, as established through an action plan developed over several years by a citizen housing committee - that, and locating more permanent housing for his family. He, his wife of two years, Lindsay, and their 1½-year-old daughter, Nova, have been living in a granny unit in Sebastopol since March 2018.

His leap into the hot seat of a Bay Area housing job came after spending the past year as a new resident of the North Bay and stay-at-home dad while Lindsay worked toward her philosophy degree at Sonoma State University, with plans to attend law school.

Ultimately, the role in Healdsburg lured him back to work at a critical time.

The housing crisis continues to grow in the region and statewide, political will is mounting for a rapid response, and Healdsburg, he said, appears to have the resources to make its own headway.

“They want to see a community that’s balanced out between tourism ... and still has the environment of their home,” said Sotomayor. “Part of that is the people who work here should be able to afford to live here. And that’s a very simple statement to say, but in practice it’s very difficult just because of the market that exists in this community.

“But I think one of the things that we genuinely can do is to continue to build out stock that would attract younger families to the area,” he continued. “It’s about a healthy community, not just about the housing.”