📮 Orlando mailman who walks 14 miles a day, featured in children’s book

ORLANDO, Fla. – You may remember Dennis Winston. The 20-year veteran mail carrier with the U.S. Postal Service who walks 14 miles a day.

It was the residents in Colonialtown who caught our attention in 2022 with a social media post, bragging about how Winston goes above and beyond his daily duties.

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“He works his fanny off and always has a positive word, always a smile,” said neighbor Lisa Singleton.

“He’s tall and I had some lights still up for Christmas and he helped me take them down real quick,” said neighbor Nina Vu.

Rain or shine, Winston is on foot keeping the mail flowing, even though being a mailman is sometimes a thankless and demanding job.

“Someone’s got to do it... I never saw myself as a mailman, but I never knew what it entailed. I didn’t realize I was going to interact with so many people and become friends with people I’ve met. It’s fantastic. Now I wouldn’t trade it, I’m good,” Winston said.

Winston spreading positive energy.

In 2022, News 6 Insider Guide Crystal Moyer spent several hours walking the route with Winston as he delivered mail on foot, in the rain.

Nearly a year later, Moyer sat down with Winston to see how things are going.

“After seeing your personality, your perseverance and just how you had such a great positive aura about you in all the elements - it was raining out there - you still had a smile on your face,” said Moyer.

“The post office has been good for me. I never saw myself as a mailman but once I got into it and learned how to do everything, it’s been smooth sailing ever since,” said Winston.

Winston even caught the attention of a local author and is featured in a children’s book.

“It was Kishor Desai wrote a children’s book called ‘What do I want to be when I grow up?’ and he included me in it. I’m delivering his mail one day and he said he had something for me and he hands a book to me. Then tells me to turn to a specific page and there I am,” said Winston. “I’m super humbled. Nothing like that has ever happened to me.”

Winston is already facing some challenges in 2023. He’ll be undergoing surgery to repair torn ligaments in his ankle. Meantime, he’s making deliveries in an ankle brace.

“It stems from my time serving in the Army. I used to get a lot of ankle sprains,” said Winston. “I could marinate on the surgery, what’s going to happen but that’s not going to do me any good.”

Winston said recovery is expected to take about two months, but is concerned he may not be back walking the streets of Colonialtown doing what he loves.

“A lot of these people are like family and friends. I’ve been doing the same route for nine years and you build a rapport with people,” said Winston. “I let all my Colonialtown people know and they sent me their best wishes. Hopefully, I’ll be back. We’ll see how the recovery goes.”

Winston hopes while he’s at home recovering, his message of kindness will carry on.

“It’s just nice to be nice. I was taught a long time ago you get more with honey than you do with vinegar,” said Winston.

Winston’s surgery is scheduled for late January. You can wish him well by leaving a comment below.

If you have a tip for an Insider story feel free to send them to Crystal Moyer. Whether it’s a new attraction you want her to check out, a community leader getting results or a hidden gem in your neighborhood, you can email your story pitch to cmoyer@wkmg.com.

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