Spirit of the Vineyard Award goes to Richard Leonard

Richard Leonard — Courtesy Vineyard Village at Home

The Spirit of the Vineyard Award for outstanding contributions to the community as a volunteer will be awarded this year to Richard Leonard.

Leonard has volunteered for several Island organizations, including Habitat for Humanity and the Lions Club; his contributions included helping to find funding for the Dukes County Regional Housing Authority’s first project at Sepiessa Point in West Tisbury, and he’s served on a number of local boards, including the Island Housing Trust.

The Vineyard Village at Home annually sponsors the award for those who have volunteered for one or more nonprofit organizations on the Island, and whose work has made a difference to individuals and to the community as a whole. Nominations are made by the public.

Leonard was born in Oak Bluffs, the last of seven children of Howard and Marjorie Leonard. 

Howard Leonard was one of the founders of the Striped Bass and Bluefish Derby, a member of the board of Big Brothers Big Sisters, and a youth sports coach. He introduced his son to those activities early in his childhood. Marjorie Leonard served on the school committee that built the regional high school.

Howard and Marjorie were known to be quiet and effective at getting things done, and Richard Leonard has followed their lead. He was a three-sports letterman in high school, and reported on Island sports for the Vineyard Gazette. He coached youth basketball, sometimes coaching four teams at a time. And he has helped run MV Youth Basketball for years.

A press release from the Spirit of the Vineyard Award says that when Leonard was 15, Robert W. Kelley, president of Edgartown National Bank, asked him to come to his office. It turned out that Leonard was interviewing for a job he hadn’t known he’d applied for, and he was hired to work after school in the accounting department. 

After college, he returned to the bank. When his boss, Mel MacKay, went away for a three-week vacation, Leonard was left in charge of mortgage lending. He went out into the streets, and said to some of those he met, “Come on in to the bank, and let’s see how we can finance a house for you.” When the boss returned, it took two days for the bank to review the mortgages for “Richard’s good people.”

His interest in helping people find housing has continued throughout his life. He discovered a low-interest federal grant that helped fund that original Dukes County Regional Housing Authority project and its work on affordable housing. 

Leonard was also one of the initial board members of the Island Affordable Housing Fund, working to get Community Preservation Act funds approved in all Island towns and contributing to affordable housing.

Leonard also helped transition nonprofit housing development from the Island Affordable Housing Fund to the then newly formed Island Housing Trust, where he served as president for the first 15 of his almost 20 years on the board.

Over his career as an Island banker, Leonard worked at the Martha’s Vineyard Co-Operative Bank, serving as president for 20 years until it merged with the Dukes County Savings Bank. Martha’s Vineyard Co-Operative Bank and Dukes County Savings Bank would eventually become Martha’s Vineyard Savings Bank. He retired briefly before becoming Martha’s Vineyard regional president at Cape Cod Five Cents Savings Bank.

While at MV Co-Op, he and Patty Leighton began the school bank program that still runs in the Island schools, teaching children from kindergarten through eighth grade the value of savings and how to manage their money. “Kids make me smile and laugh every day,” Leonard is quoted in the release. 

He also followed his father onto the board of Big Brothers Big Sisters. 

Leonard’s volunteer work includes the Lions Club and his tenure as treasurer of the Nathan Mayhew Seminars. He has been on the board of You’ve Got a Friend for more than 20 years, and has served on the Greenough House board since 1995, overseeing a major rehabilitation of the senior housing building into six independent-living units.

He credits his effectiveness to his belief in empowering, encouraging, and trusting those he works with.

When asked what he would advise others to do, he said, “Get involved. Say yes.”

There will be a gathering to honor Leonard on Friday, May 19, at the P.A. Club at 4 pm. Refreshments will be served; cash bar.


  1. It would be hard to find someone more community-minded than Richard Leonard. His mother, Marjorie Leonard, was my sixth-grade teacher at OB Elementary. She was one of my favorite teachers, sensitive and caring. She saw the true potential in every child. In this case the apple didn’t fall very far from the tree. Congratulations Richard.

  2. Congratulations Richard, what an amazing community man you are.

    Richard helped me buy my first car… I was getting a loan at the bank for my first car and I was thinking to buy a new one in 1997 or so. He suggested, I would want to buy a used one due to the boat rides and people dinging my car when the door opens and how that would be a heartache with a new car… when done Richard; Brilliant. Thank you for all!

  3. Nice andhappy for him. A deserving man . Does anyone know where Mr. Kelly’s daighter Sandrais now? I knew herwhen we were teens.

  4. They need to add humility to Richard’s list of attributes. I’ve known him for decades (in a variety of roles); and, while I was always impressed with his business acumen I had no idea he was also a humanitarian and native islander. They couldn’t have picked a better recipient. Congrats Richard.

  5. Richard is an excellent choice for this award. He and his wife Pia exemplify all that is good with humanity. Their commitment to family and friendships and contributions to our island is outstanding. Proud to be their friend.

  6. Dont stop now !!congratulations-well deserved-best wishes from an old friend-trip

  7. This award could not go to a more deserving person.
    Richard helped me get a mortgage when I had a complicated situation.
    We love you Richard.

  8. Look up pillar of the community and you’ll find a picture Richard Leonard! Great guy working hard to make our community better.

  9. Without question he deserves it and stands above so many who truly give generously to this island of their resources.

  10. Richard went above and beyond for us many years ago as we approached building, with practical help, kindness, suggestions, and encouragement. A Vineyard blessing, he is!

  11. Richard Leonard..such a great choice for this honor.
    Besides so many other roles, let us remember to add
    Coach, for years of rec and West Tisbury girl’s basketball
    Teams. Watching this fine civic leader become a competitive
    Powerhouse among the drama and talents of adolescent girls
    was a teaching experience to remember. Congratulations Richard,
    And thank you.

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