Richard Leonard, banker and much more

By Brien Hefler
Published: September 10, 2009

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On the occasion of their 25 anniversary, Pia Leonard gave her husband, Richard, a copy of Ralph Waldo Emerson's poem, "Success," written in calligraphy. Among the poet's musings on what makes someone successful, there is this: "To leave the world a bit better, whether by a healthy child, a garden patch or a redeemed social condition; to know even one life has breathed easier because you have lived."

Richard Leonard, who has coached and mentored dozens of Island children and devoted much of his life to helping the Martha's Vineyard community, appears to have taken the poet's formula to heart.

Vice president and chief operating officer of Martha's Vineyard Savings Bank, Mr. Leonard has spent most of his life on the Island and his entire career in banking. He began in finance at the age 15, working one summer at the Edgartown National Bank, under the tutelage of Robert W. Kelly.

An Oak Bluffs native, Mr. Leonard earned a degree in management at UMass Amherst and moved to Houston for a job, when he graduated in 1983. But on a visit back home that summer, his friends on the Bandits, a men's fast-pitch softball team, convinced him that he should stay. He took their advice.

He was 25 when he moved to the Martha's Vineyard Co-Operative Bank, eventually serving as president until it merged with the Dukes County Savings Bank in 2007.

For Mr. Leonard, banking is about community: "Banking is a community atmosphere. It's more about working with people than working with numbers. As a businessman in a small community you are on call all the time... wherever you are."

And while many Islanders are distinguished by their generosity as volunteers, Mr. Leonard has quietly become significant - often a founding member - in a remarkable number of Martha's Vineyard's charitable and nonprofit organizations: chairman of the Island Housing Trust's board of directors for six years running; founding board member of the Island Affordable Housing Fund; and, among others, a former member of Big Brother Big Sister of Martha's Vineyard. He coaches Martha's Vineyard Youth Basketball, and he served as the girls basketball coach at Martha's Vineyard Regional High School (MVRHS) for three years. He helped teach Island children the fundamentals of the game with the Martha's Vineyard Hoop Club and with students at West Tisbury Elementary School. The Leonards have two college age girls, both athletes.

Lisa Stewart was coaching the Oak Bluffs School's girls basketball team when Mr. Leonard coached the West Tisbury School's girls team.

"Everything he does, he throws himself into with amazing enthusiasm, with 150 percent effort. When he was coaching the West Tisbury team, the girls just adored him. He acted like they were the most important team on the whole Island. He got them to overachieve, and they ended up beating us in the final game.

"Never a negative word comes out of his mouth. His whole thing was teaching life lessons to the kids, not just winning. He's a competitive guy, but it's always fair, square, and above board," Ms. Stewart said. "His voice is very loud and he's always yelling encouragement.

Ms. Stewart, who is also active in the Martha's Vineyard Hoop Club, mentioned the work Mr. Leonard put into helping organize fundraisers for the club. "We were able to take all the checks and just dump them down and have him take care of it all," she said. "It was like having a little angel. I just can't say enough about him."

Since the age of 25, when he joined the Martha's Vineyard Lions Club, Mr. Leonard's community involvement has grown exponentially. Why?

"It's just the sort of thing you do," Mr. Leonard says. "It is a lot of work, but there are a lot of wonderful people to work with in the community."

Mr. Leonard's dedication may well be hereditary. His, father, Howard W. Leonard, helped organize the first Striped Bass and Bluefish Derby, worked with the Martha's Vineyard Chamber of Commerce, was president of the Oak Bluffs Senior Center, and volunteered with Meals on Wheels. Mr. Leonard's enthusiasm for sports reflects his father's interests also. Howard Leonard was the Vineyard Gazette sports reporter for many years.

Richard Leonard's mother, Marjorie, a sixth grade teacher in Oak Bluffs, served as the Oak Bluffs representative on the original Martha's Vineyard Regional High School school committee, worked with the Oak Bluffs Homemakers Club, and was an active volunteer while also raising seven children.

"Part of my involvement with [the organizations] was growing up here and seeing how difficult it was to afford to live here; it seemed like a natural fit," Mr. Leonard says.

About 10 years ago, Mr. Leonard joined You've Got a Friend (YGAF), a nonprofit organization, run entirely by volunteers, that raises relief funds for families that have suffered the loss of a head of household or similar catastrophic event.

"It's one of those organizations you wish there wasn't a need for," he said, "but it allows the community to reach out and help families in need."

A West Tisbury forum on income versus housing years ago prompted Mr. Leonard's work with the Island Affordable Housing Fund as a founding board member, and later his work with the Island Housing Trust (IHT), where he serves as president.

Philippe Jordi, IHT's executive director, has known and worked with Mr. Leonard for six years. "I can't say enough about him," Mr. Jordi says. "He has the sensibilities of a good businessman, and he has the passion of a community organizer. He has this great combination, and I think people are drawn to him. Richard is able to do things because he knows the community context so well and the people on the Island."

Mr. Jordi credits Mr. Leonard for organizing a civil, thorough discussion and helping the IHT's Bradley Square project at the corner of Masonic Avenue and Dukes County Avenue in Oak Bluffs.

Mr. Jordi says he considers Mr. Leonard's willingness to put in time and hard work as two of his most outstanding qualities: "When he believes in something, he goes the extra mile," Mr. Jordi said. "What I see about him is he really believes in the human spirit and always brings out the best in people."

For Mr. Leonard, it's simple. "We all have our challenges. Life is busy and full. But when you do something for someone else, all that goes away."

Brien Hefler is a freelance writer who divides his time between Tisbury and Baltimore, Md.

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