At 63 years old, Richard Leonard said he’s not ready to receive the Spirit of the Vineyard Award.

The community banker, philanthropist and housing advocate has been working on the Island since his teen years, taking his first job in banking at 15 and rising to CEO of Martha’s Vineyard Cooperative Bank at age 29. After decades serving the community in a variety of roles, he will receive the prestigious Island award on Friday, May 19 in a ceremony at the P.A. Club from 4 to 6 p.m.

But one year into his retirement, he said he still has more to give.

“I’m not done,” he said in a recent interview with the Gazette. “I’m not putting as much pressure on myself...but I didn’t think of myself as done.”

A third generation Islander and the youngest of seven children, Mr. Leonard grew up among a wide variety of Vineyard characters, from the grizzled fishermen who would frequent his parents’ sports shop in Oak Bluffs (now Jim’s Package Store) to the summer residents who would pour in from every corner of the globe. He remembers most fondly the odd jobs he took on to keep busy.

“I had a newspaper route that was so extensive I had to get subcontractors,” he laughed. “I got paid $10 to do it. I told the other kids I’d give them $8 to help me, and then I’d get $2 for doing nothing.”

In high school, his enterprising nature attracted the attention of Robert W. Kelley, then the CEO of Edgartown National Bank. Looking to get in touch with Mr. Leonard, Mr. Kelley called him at the school.

“I got a call to go to the principal’s office and they said I had a call from Mr. Kelley,” Mr. Leonard said.

Mr. Leonard went to Mr. Kelley’s office after school for a conversation and the next week Mr. Leonard received another call from the principal’s office.

“It was Mr. Kelley again, asking why I hadn’t shown up to work all week,” he said with a booming laugh. “I had no idea I was even interviewing for a job, let alone hired.”

From that point on, Mr. Leonard worked summers at the bank, eventually returning for a full-time job after graduating from the University of Massachusetts-Amherst. He went on to take a job at the Martha’s Vineyard Cooperative Bank, where he became CEO just four years later. In 2007, MV Co-op Bank and Dukes County Savings Bank merged, becoming MV Savings Bank. Mr. Leonard served as executive vice president there until 2013. He was named regional president of Cape Cod Five in 2014.

“I’ve been very, very fortunate,” he said.

In adulthood, Mr. Leonard bears little resemblance to the Tom Sawyer-esque schemer looking to make a quick buck. He credited his four years in the UMass economics department for widening his scope.

“The economics professors were a bunch of Marxist-Leninists,” he said. “They taught that success was not based solely on a dollar, and winning meant floating all boats, not just one.”

He said that attitude informed his approach as a community banker, prioritizing people and employees over stockholders. In retrospect, Mr. Leonard said he first learned those values from his childhood on the Island.

“Growing up, there was always a sense of community responsibility,” he said. “If someone asked you to do something, you just said, ‘Yes.’”

It’s also that sense of community responsibility that led him to serve on the boards of Martha’s Vineyard Chamber of Commerce, Big Brothers, Big Sisters, and You’ve Got A Friend. The latter, he explained, is like a community-based GoFundMe to support families with medical expenses and other costly emergencies. Unlike other relief aids, he said, this organization also helps families with the tangential expenses that may build up during hard times.

In his spare time, Mr. Leonard coached four different girls’ youth basketball teams, as a means to support his daughters’ budding athleticism. Coaching soon took over his life, although he said he wouldn’t have had it any other way.

“I would ask to leave the bank early for practice and [fellow board member] Jeff Norton would say, ‘What does it matter what we say? You’re just going to do it anyway,’” he said.

“I loved those girls,” he added.

Mr. Leonard’s primary crusade, however, has been housing issues. He served as president of the Island Housing Trust for 15 years, encouraged all six Island towns to adopt the Community Preservation Act, and had been intimately involved in the first attempts to secure the all-Island housing bank.

But after spending 20 years on the issue, he expressed disappointment at how little action has been taken since he first started ringing the alarm bells about the Island’s housing affordability crisis.

“None of us like change, but the only thing constant is change,” he said. “To do nothing is a decision, too, and it’s not necessarily the right one.”

For Mr. Leonard, regionalization is the natural next step the Island should take to address housing.

“I grew up playing Little League baseball, and back then you played for your town team,” he said. “Years ago, they adapted to an all-Island Little League...Now you have children interacting across towns, making friends...Doing that hasn’t hurt us at all. In fact, it made us stronger.”

For now, Mr. Leonard has taken a step back both from banking and his advocacy work to focus on family — his wife, Pia, his daughters and his four grandchildren. He retired from his role as regional president of the Cape Cod Five Cents Savings Bank in 2022.

“I’ve been going all my life,” he said. “I haven’t played guitar enough. I haven’t fished enough...Today, I’m going to mow my lawn and clean the deck. I’m just going to pop in my headphones and get it done. How’s that for slowing down? But that’s good. I need it.”

He said the award, if anything, is a reminder that he can step back in anytime.

“Now I’m gonna feel guilty as hell if I don’t help,” he laughed.