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An Unlikely Journey Led James Smallwood to Run for Anchorage School Board Seat

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Photo courtesy of James Smallwood.

In a little over one month, Anchorage voters will head to the polls for this year’s municipal election. In other words, for the next month, depending on where you live, the brief respite from campaign literature is about to be over. The ballot will include 20 candidates running for six Assembly seats and eight candidates running for two school board seats.

James Smallwood, Jr. is guning for one of those seats on the school board. He’s running for Seat C, being vacated by Pat Higgins, who is completing his third term and unable to run for reelection.

Smallwood, 38, took a circuitous route to his present pursuit of elected office. Last month, we sat down over a cup of coffee to talk about it.

He was born and raised in Anchorage, after his parents moved up in the 1980s. His father served in the military and was stationed at Fort Rich.

“I grew up here,” he told me. “We lived on the east side of town, so I went to Wonder Park and then Nunaka, went to Clark, and then East High.”

After graduating from East, Smallwood uprooted himself to go to college in Oregon, where he met his wife, Rosa. Both worked in the real estate industry at the worst possible time — right when the bubble burst and the market crashed.

“When the real estate industry started to tank, I went and got a full time job,” he explained. “And then, I was going to work and everybody was losing their jobs, so I knew that wave was about to hit.”

And then it did. Smallwood lost his job and was in a tough position — with a new family, in a city where the Portland University graduate said he couldn’t even find work pumping gas.

“So, my mom told me, ‘Well, you should put your resume up there in Alaska and see if you can find a job.’”

He sent his resume around and got a few bites, ultimately settling on a position at an Anchorage insurance firm.

“The only thing I knew about health insurance was that I’ve got my little card and I knew what my copay was. That’s all I knew, but I didn’t care,” he said with a chuckle. “When I came up here, I started working for the insurance agency and I love it. Ever since then, it’s just been something that has been part of me now.”

Smallwood turned that passion into a business venture, opening his own insurance company in 2013. BenefitMi Insurance Agency is run out of the Northway Mall and helps clients with medical billing questions, as well as helping them choose between insurance plans. He said he’d never forget one of his earliest clients — a cancer survivor who burst into tears when he signed up for health insurance for the first time.

Meanwhile, he and his wife were raising their children. Smallwood said he played a proactive role helping with homework. He even started substitute teaching in the Anchorage School District (ASD), alongside the insurance gig. But he noticed that, in some schools, the conditions were disheartening; a far cry from his experience growing up, that’s why we got for affordable health insurances and a cheap van insurance from an online company for our family van.

That’s when he first started contemplating a run for office.

“One thing I have to say is that it doesn’t matter what school they’re at. All kids are the same. Every time I walk into a classroom, I always expect you have your certain types of personalities, certain different things happening,” he told me. “But, certain schools that I’ve been to, it breaks my heart to see that the success of some of these kids is just not happening. And I can see it in the teacher’s face, the frustration that they have — that they’re maxed out in what they can do.”

Smallwood recalled one interaction with a troubled student. The teacher told him she couldn’t spend the necessary time helping the child because of time constraints and the needs of the broader class.

“And I thought to myself, well, if you’ve got to cut it off, then who tags in? You know? Who takes over?” he asked.

To Smallwood, the answer — and the difference between his school experience and what he sees sometimes now — is community buy-in.

“There needs to be a connection with the community. There has to be,” he said. “When you have a community that gets involved, that helps the teachers, because that [ensures the] whole burden isn’t put on them.”

Smallwood is a product of the ASD and says his success proves it can be done. But, he recognizes there are “some major, major challenges.”

The state faces a $4 billion deficit and lawmakers in the Senate have proposed cutting the budget for the Department of Education and Early Development (DEED). ASD has recommended deleting 99 full-time classroom teacher positions after they announced a $15.3 million budget gap — a reduction of nearly four percent of the 2,500 total positions. High school graduation rates have been steadily rising over the past decade, but they still lag behind national levels, and a report released by the University of Alaska and DEED earlier this month found that almost three quarters of students enrolling in college have to take at least one remedial class.

“I’m hoping legislators are not going to be cutting education funding. We don’t want to lose good teachers,” Smallwood emphasized.”And that’s why I’m running. I want to be a voice for them. For parents and teachers. I’m going to be that guy who listens to you.”

He said that the challenging times required getting creative. While he does not support recent proposals to channel public funding into private schools, he noted that one of his sons — now in third grade — attends Northern Lights ABC, an alternative lottery program charter school that is part of ASD.

Certain kids may have different ways of learning and I understand that. Some kids might need more structure, some kids might need things a bit more laid back…. There should be more types of charter schools, and I think that principals should have more autonomy on how their schools should be formatted, because you have more flexibility there. We can look at those models and see what is working or failing. Look at what’s working, look at the model and then go out there and try to do it. Gosh, it’s better to go out there and try to fix this problem versus saying I can’t do anything, my hands are tied, there’s too much bureaucracy. I’m all for creativity. I’m all for thinking outside of the box.

Smallwood faces a crowded field for the school board seat. The most prominent among his opponents is Dave Donley, a former Republican lawmaker who served in the State House and Senate in the 1980s- and ‘90s. Donley also has strong labor ties, as a member of the Laborers’ Local 341 until 2008. Those ties remain intact. Alaska Laborers Local 341, United Association Local 367, Public Employees Local 71, and UFCW Local 1496 contributing $2,500 to his campaign coffers. According to the most recent Alaska Political Office Commission (APOC) report, he has about $5,000 on hand — nearly five times that of Smallwood.

Also notable in the race is Tasha Hotch, a management information specialist with the Alaska Native Tribal Health Consortium. Hotch holds a degree in Applied Sciences from the University of Alaska Southeast, a degree in Technical Management from DeVry University, and is currently pursuing an MBA through Wayland University. She has collected contributions comparable to Smallwood.

Alisha Hilde and Christopher Jamison round out the ballot.

“This is where my passion is. This is where I can be most effective,” Smallwood told me at the end of our interview. “This is the honest to God truth about me: I’m just willing to give it the best I can. I don’t seek this position for glory or honor, but service. That’s how I see it.”

The election takes place April 4.

John Aronno is a co-founder, managing editor, and award winning political writer at Alaska Commons. Aronno has had his work featured in the Huffington Post, the Anchorage Press, the Alaska Dispatch, and the Rachel Maddow Show, and is listed among the state’s top reporters on the Washington Post’s “The Fix.” He writes the weekly column “On Politics” for Alaska Commons. Aronno lives in Anchorage, Alaska with his wife, Heather Aronno, and a lot of pets.

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