As teachers and students prepare to start classes in September, Martha’s Vineyard Public Schools superintendent Richie Smith is sizing up the challenges ahead in his first year as the Island’s education chief — and he sees no shortage of problems to solve.

“I would argue with anyone that there are more pivotal things to be addressed this year than any year since I’ve been here,” said Mr. Smith, a Virginia native who came to the Vineyard in 2002 as a Tisbury School counselor.

Speaking on August 24 after dropping off his oldest son at college, Mr. Smith listed the biggest issues on his plate as summer ends.

One major school construction project is already underway at the Tisbury School and a second is well into the preliminary stages at the high school, he said.

“It’s obviously a challenge, but also a fantastic opportunity. We have to see it that way. We have to put our energy that way,” Mr. Smith said of the two school projects, both of which have key dates approaching.

The costly and increasingly contentious Tisbury School building project is poised to proceed, but needs a two-thirds vote at a September 20 special town meeting to reach full funding for the $81 million renovation and addition.

Also in September, the clock begins ticking on a 270-day eligibility process to determine whether the Martha’s Vineyard Regional High School qualifies for up to 38 per cent in state reimbursement for a new or rebuilt school.

“It will result in, hopefully, a feasibility study that gets voted for approval and funded [at town meetings],” Mr. Smith said.

Mr. Smith has a labor dispute on his hands as well. Contract negotiations with the teachers union are still unresolved, although agreements have been reached with the custodial, food service and educational support staff bargaining units, he said.

“We’re heading toward arbitration with our teachers union. That is unprecedented,” Mr. Smith said. “That’s another unique challenge for this year.”

The new superintendent also must shepherd the high school track and field project, another controversial plan that is currently mired in litigation between the high school committee and the Oak Bluffs planning board over the latter’s denial of a special permit for an artificial turf infield.

“That presents challenges, and it has ramifications,” Mr. Smith said of the lawsuit.

Other concerns he’s tackling as school resumes include the ongoing Covid pandemic and staff shortages, particularly among school bus drivers — a problem off-Island as well, he said.

“The challenges for our staffing are also influenced by our housing availability, but there are staffing shortages nationally,” he said.

“I haven’t even gotten to the core work of what we do, and that’s taking care of our kids,” he added.

About 2,100 students attend the Island’s public schools — roughly the same number as when Mr. Smith and his wife, Missy Smith, came to the Vineyard 20 years ago.

“We’re a tiny school system,” he said.

But while the student population hasn’t grown significantly, the system’s demographics have altered, Mr. Smith said.

“Our staff has evolved to support that change,” he said, citing more student support services and programs for children with varying needs.

“Our English language learner population has grown. The cost of living [and] economic challenges have grown,” Mr. Smith continued. “Our ability to change and answer and respond to the need, I have been very impressed with.”

At a high school conference on social justice and diversity in June, Mr. Smith told students about his own bicultural heritage.

“My mother was Japanese, and my dad was in the army,” he said this week. “They met in the occupation after World War II … She left the only culture she knew and the only family she knew to be with my American father in a land she’d never seen.”

That new land was the segregated South, said Mr. Smith, now 60.

“I got very little Japanese culture,” he said. “Richard Michael Smith: You don’t hear any Asian in my name.”

He and his wife arrived on Martha’s Vineyard in June 2002, fresh from earning their master’s degrees at the University of Virginia, Mr. Smith said.

“We had visited here and honeymooned here,” he said. “We really loved our visits.”

The couple cold-contacted Island schools for jobs, working as a team.

“We actually put our resumes together and sent them to all six schools,” Mr. Smith said.

“We just did it on a whim, and we’ve stayed here ever since,” he added.

The couple’s resumes reached their targets: Ms. Smith was hired to teach

English language arts at the Oak Bluffs School, a job she still holds, while Mr. Smith started at Tisbury School.

Their first son, Zach, was born the following year and is now a sophomore at Hamilton College in Clinton, N.Y.

Son Renny was born next, with a congenital heart defect that required multiple hospitalizations and surgeries, sometimes after being airlifted from the Vineyard, Mr. Smith said.

It was a difficult time for the young family, but Islanders rallied to support them, he went on.

“The school communities and the surrounding community just embraced our family,” Mr. Smith recalled.

“When it comes to people, there’s no better place. And I say that as a Southerner,” he said.

Now recovered, Renny is about to start his sophomore year at the regional high school, his brother’s alma mater as well.

After earning a second master’s degree, in administration, from Endicott College through Tisbury School, Mr. Smith became principal at Oak Bluffs School until 2015, when he and off-Islander Matthew D’Andrea were the two finalists for the top school system job.

“Matt won the position, and he was the right person,” said Mr. Smith, who became assistant superintendent at Mr. D’Andrea’s request. “He asked me, which I’ll never forget,” Mr. Smith recalled. “Who asks their rival to be their assistant? That was a great move, a strong move. He became a really good friend to me, and a good boss.”

While working for the school system, Mr. Smith also earned a doctorate in educational policy and planning through an executive program at William and Mary College, he said.

When Mr. D’Andrea left this summer for a mainland job with two years left on his contract, Mr. Smith agreed to serve out the remaining time, but not as an interim administrator.

Instead, the school committee agreed to hire him as superintendent for the two years, and to decide after the first year whether or not to search for a replacement.

“I’ll support the search process and I’ll support the transition,” Mr. Smith said.

If he’s replaced, Mr. Smith said, the family will stay on Island until Renny graduates, and then he and Ms. Smith likely will head back to Virginia, where she still has family.

But he’s hoping that the year to come will show the school committee that he is a keeper.

“If folks want me to finish my career here, we will finish our careers here,” Mr. Smith said.