šŸ“® Orlando mailman who walks 14 miles a day, featured in childrenā€™s book

Dennis Winston prepares for ankle surgery, not prepared for time away from what he loves

ORLANDO, Fla. ā€“ 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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ā€œHe works his fanny off and always has a positive word, always a smile,ā€ said neighbor Lisa Singleton.

ā€œHeā€™s tall and I had some lights still up for Christmas and he helped me take them down real quick,ā€ 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.

ā€œSomeoneā€™s got to do it... I never saw myself as a mailman, but I never knew what it entailed. I didnā€™t realize I was going to interact with so many people and become friends with people Iā€™ve met. Itā€™s fantastic. Now I wouldnā€™t trade it, Iā€™m good,ā€ 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.

News 6 Insider Guide Crystal Moyer shooting story with mailman Dennis Winston (Copyright 2022 by WKMG ClickOrlando - All rights reserved.)

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

ā€œAfter 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,ā€ said Moyer.

ā€œThe 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, itā€™s been smooth sailing ever since,ā€ said Winston.

Winston even caught the attention of a local author and is featured in a childrenā€™s book.

ā€œIt was Kishor Desai wrote a childrenā€™s book called ā€˜What do I want to be when I grow up?ā€™ and he included me in it. Iā€™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,ā€ said Winston. ā€œIā€™m super humbled. Nothing like that has ever happened to me.ā€

Winston featured in 'What do I want to be when I grow up?' children's book (Copyright 2022 by WKMG ClickOrlando - All rights reserved.)

Winston is already facing some challenges in 2023. Heā€™ll be undergoing surgery to repair torn ligaments in his ankle. Meantime, heā€™s making deliveries in an ankle brace.

ā€œIt stems from my time serving in the Army. I used to get a lot of ankle sprains,ā€ said Winston. ā€œI could marinate on the surgery, whatā€™s going to happen but thatā€™s not going to do me any good.ā€

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.

ā€œA lot of these people are like family and friends. Iā€™ve been doing the same route for nine years and you build a rapport with people,ā€ said Winston. ā€œI let all my Colonialtown people know and they sent me their best wishes. Hopefully, Iā€™ll be back. Weā€™ll see how the recovery goes.ā€

Winston hopes while heā€™s at home recovering, his message of kindness will carry on.

ā€œItā€™s just nice to be nice. I was taught a long time ago you get more with honey than you do with vinegar,ā€ said Winston.

Winstonā€™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 itā€™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.

You can listen to every episode of Floridaā€™s Fourth Estate in the media player below:


About the Author:

Crystal Moyer is a morning news anchor who joined the News 6 team in 2020.

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