Leaving his post

Longest serving Island postmaster set to retire.


For many who get their mail at the Oak Bluffs Post Office, the joyful wit and bright smile of postmaster Paul Leonard is a welcome part of their day.

Born and raised in the heart of Oak Bluffs near Nashawena Park, Leonard has been a part of the Island his whole life –– helping the community get its mail for the past 35 years.

Leonard, who is set to retire June 1 as the longest serving postmaster on the Island, began his career with the Post Office at 12 years old working with his father, doing special deliveries on his bicycle for the Oak Bluffs Post Office at 25 cents per letter. Once he finished high school he worked as a temporary employee for the Post Office during the summer.

After four temporary stints at post offices on the Island, Leonard moved off Island to go to school He also married his wife Linda whom he met on the Island one summer.

Leonard took the civil service exam, promoted by his father Howard Leonard, a former postmaster in Edgartown who said it would one day come in handy. About two years later, in 1983, Leonard got a call from the Tisbury postmaster offering him a job. Eager to get away from life in the city, the Leonards moved to the Martha’s Vineyard.

He worked at the Tisbury post office for 10 years, becoming supervisor the day his daughter was born in 1987. In 1993, he got another call and took his current job as postmaster in Oak Bluffs. “Be a postmaster in your hometown, it’s got sort of a nice ring to it,” Leonard said.

After 25 years as the Oak Bluffs postmaster, Leonard has learned a thing or two about the people of the Island’s biggest town. “I’ve been there so long I sort of know everybody, I know generations,” he said. “I’ve known these people for 50 years. My school teachers are still customers, the people I used to get halloween candy from are customers, kids I coached in basketball and baseball are my customers and now they have children. It’s a little overwhelming when I think back on it, but it’s been very rewarding.”

With such a lengthy career, Leonard has seen the implementation of automation in the mail service and the incorporation of tracking numbers which he described as a “godsend.”

Being an exclusively walk-in post office, Leonard has formed a camaraderie with the people of Oak Bluffs over many years of face-to-face banter, a diligent attention to his work, and a keen eye of Island happenings saying many of his customers feel like family.

Every Thursday, Leonard opens the paper to read the obituaries, the births, the Oak Bluffs town column, and the letters to the editor. “That tells me what’s going on in people’s lives that week. Who I might want to acknowledge a death of, or congratulate for a birth, or whose birthday is coming up.”

One winter, a letter arrived for “Grandma and Grandpa.” Leonard knew the address and the grandparents. Being regular customers, he also knew they were staying in Florida for the offseason and were getting their mail forwarded to them so he slapped on their names and mailed it down to them. A few weeks later, they returned to the Island and told Leonard they had no idea how he got the letter to them, but were grateful that he did.

For Leonard, time flies when you’re having fun. “The days never dragged on, the years never dragged on,” he said. Last March, he was surprised to see the date next to his name on the plaque of Oak Bluffs post masters –– realizing his tenure of 25 years had surpassed his mentor and predecessor, Robert Hughes. It was a special moment, Leonard said, because he felt it was a great way to honor the man who taught him how to interact with customers at the Post Office.

Having been a constant in people’s lives for many years, Leonard’s reputation is well known around town.

“We do a lot of mass mailings that we print here. Of all the postmasters I’ve worked with on different mailings he is the best to work with when you got something to send to the Post Office. We will miss him,” Tony daRosa, owner of deRosa’s-Martha’s Vineyard Printing said.

“He’s a great guy, ran a good Post Office, always wonderful service, no problems whatsoever,” Donna Pacheco, manager of Reliable Market said.

Susan Phillips, the manager of Phillips Hardware who has known Leonard since high school, said she was, “sad to see him go.”

Bill Stafursky, a longtime Island resident and customer at the Oak Bluffs Post Office, told The Times that Leonard will be a tough act to follow. “He grew up in Oak Bluffs, he’s been such an integral part of the community,” Stafursky said. “I don’t know how you replace someone like that. You’re never going to get someone with the same understanding of the community and their needs.”

When asked what advice he has for the next postmaster, Leonard replied, “I had the advantage of knowing the people and knowing the people helps. In this particular office, I think it’s important for the postmaster to make their presence known in the office, get to know the people because they’re a lovely group of people. Get a little involved, they’re very very good people.”

Thinking back on a long and dedicated career in public service, Leonard got emotional: “I’m overwhelmed. I never expected any of this. I just came in to do a job to the best of my ability and I certainly appreciate all the support and thanks I’ve been getting. I’ve been blessed. I’ve known most of [the community] my whole life. It’s been nice that they’ve allowed me to take a little bit of their life, to share that piece with them. Not to get involved too much, but to have that one moment when they come in and we have something in common that we can exchange. Whether it be a birth, going to a sporting event with grandchildren, or an achievement in school. There’s something I can find and that’s always been nice.”



  1. Paul was so wonderful and helpful in helping to get our POB set up and providing information when we were moving to the Vineyard. When I went to the PO the first time and gave my box# to pick up a package he said “Oh..the Cobbler’s wife” – just by my box#. Great service…very nice man…and we are sorry that he will be leaving this post!

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