- December 4, 2025
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Photo by Thomas Lightbody | TK Photography
The mayors of Winter Garden, Oakland, Ocoee and Windermere have lived in their respective communities for decades and have seen firsthand how the communities have grown and changed, all while preserving their communities’ histories.
Over the years, they’ve picked up the West Orange Times & Observer and Southwest Orange Observer as trusted sources for the news happening in their communities.
From government meetings to local events to individual celebrations and losses, the mayors have seen it all in the local, community newspaper.
The mayors reflected on how The West Orange Times & Observer and Southwest Orange Observer have impacted their communities.
Throughout the newspaper’s history, Winter Garden Mayor John Rees said the West Orange Times & Observer has been a source for the local news of what’s happening in town, events coming up and more. He’s watched the paper grow to cover more than solely Winter Garden.
“When we were growing up here, it was mainly Winter Garden,” he said. “We had some Ocoee and stuff in Oakland, but it brought the news to Winter Garden of what was going on in your area, what you can expect, what was coming into town, what the events were. I think it just kept everybody in town informed. Growing up, everybody looked forward to getting the paper.”
Rees has been reading the newspaper since he first learned to read at 5 years old. He recalled The Winter Garden Times and the Orlando Sentinel were delivered to his home as a child.
Growing up, he remembered seeing his Little League team in the paper and when Lakeview High’s basketball team was a runner-up at the state championship. As an adult, Rees and his wife had their wedding picture in the paper.
He said being in the paper gave him bragging rights, sometimes even going around and asking for the autographs of the people in the newspaper.
“As kids, you grab the paper and you run around, ‘Hey, look at that, we’re in the paper. Oh, we don’t see your picture anywhere, sorry,’” Rees said laughing. “It was fun with your friends. Most people like my cousins that might have been in California or Ohio in bigger cities, they didn’t have that. For us to take the page of the paper and send it to them was pretty neat.”
Every time Rees looks at the paper now, he always is sure to look at The Ways We Were, which showcases the communities’ histories from at least 80 years ago until now.
“If you were to ask a lot of the people that grew up here, I think a lot of them really, really enjoy reading and reminiscing about something that happened 75 years ago,” he said.
Windermere Mayor Jim O’Brien has been reading the West Orange Times & Observer and the Southwest Orange Observer since before he and his wife moved to Windermere in 2004.
“The Observer has been a mainstay of the town of Windermere since its inception with the Bailey family residing in town,” he said. “The greatest impact the Observer has had over time is the deeply personal way they follow the people and stories that impact our friends and neighbors. The relationships between the town of Windermere and the Observer staff is unique with a deep understanding and trust built over decades. We value the local content that keeps our community informed and connected.”
Over the years, he recalled seeing his children in the pages of the paper, including in the coverage of the town’s Easter egg hunts and Halloween event in 2008.
When O’Brien became involved in the town of Windermere’s committees and elections, he saw himself in the paper as there was coverage of his family and his vision for the town in 2010.
“Local election coverage was a hallmark of the Observer and valuable to voters throughout West Orange County,” he said.
Every week, O’Brien looks forward to reading the “positive coverage of people who work to make life better for our town and the West Orange community.”
Ocoee Mayor Rusty Johnson has resided in the area for 69 years.
The Ocoee High School graduate has grown up with the Orange Observer’s presence and now has the ability to see how it’s impacted him as well as the community members in his area of Ocoee.
Johnson has read the paper since as long as he can remember, after turning old enough to be able to read. During his Boy Scout days, his group was featured once, but he doesn’t recall being featured individually.
Over time, he’s been able to see how the Observer has evolved. He’s noticed differences in how it’s presented and the styles used, but he views it as a positive.
“Everything changes, the different ways presented in the paper and things like that, but that’s good,” Johnson said. “Everything changes for the better; it’s just moved to the better.”
He particularly enjoys “The Ways We Were” section, which highlights West Orange’s history. It presents old advertisements, historical figures and events that happened in the area years ago.
“(It) might have something 50 or 60, years ago, something we were involved in or my father-in-law for instance,” Johnson said.
Having lived in the area since 1955, Johnson and his wife have been able to see many of their relatives featured in the Observer. When he sees the history section, they can recognize different things and people and reflect on that time in their lives. Both of their children have made it into the paper, including when his daughter graduated in 1987 and was a debutante, and his son played baseball.
Johnson loves that the Observer strives to serve the local community, covering high school graduations, a Little League team’s success, small local businesses and more.
“I read every little thing about it to see what’s going on in the area,” Johnson said about the Observer. “That’s the good thing about it. It has local (news), Winter Garden to Oakland, Windermere and us (Ocoee) so it’s good.”
The localness of the paper is exactly what Johnson believes helps Ocoee. He said it’s a positive that the people in Ocoee get to see how their town and surrounding areas are doing. Without it, they might’ve missed the news otherwise.
Johnson specifically looks out for the obituaries in the paper. They serve as a way to notify the local community about those who have passed away and sometimes is the only way they know about their passing.
Shane Taylor recalled being a kid and hearing the siren on the old water tower at the old fire station, where SOBO Art Gallery currently is located in Winter Garden, to let everyone in the surrounding packing houses know it was time for lunch.
He remembered, depending on which way the wind blew, he could smell the juice plant making concentrate in Oakland or Ocoee as he made his way to high school.
Taylor said as a member of the West Orange High School band, he’s sure he was featured in The West Orange Times & Observer.
Every week, Taylor, now the mayor of the town of Oakland, looks forward to reading The Ways We Were feature in the newspaper as a flashback to “the way we were back in the day,” he said.
“There’s a lot of people who are new here that don’t understand the history of the town or the community,” Taylor said. “It was a citrus community is what it was way before Disney showed up. … Just the smell of the citrus plant, the orange trees, all that stuff, I know it’s corny and crazy but I’ve never had the desire to sit there and go, ‘I’m leaving, I want to get away from this.’ No way.”
Just as the West Orange Times & Observer did 120 years ago, Taylor said the newspaper continues to be a “very informative” source of news.
“It’s one of those medias that you can go to if you want to know what’s really happening in town,” he said. “It was always a feel-good paper. Very rarely did you have something in there that was negative, so that was good. Growing up with that and seeing that, it’s a very informative piece.”
