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West Orange Times & Observer Wednesday, Mar. 4, 2020 8 months ago

1954-2020: Former Winter Garden fire chief Randy Dollar dies

Dollar led the city’s department during an era of growth and change.
by: Amy Quesinberry Community Editor

Randy Dollar was hired as the first full-time fire inspector for the city of Winter Garden in 1974, and his job was to search buildings looking for potential fire hazards. He remained in that position for 11 years — all the while rising through the ranks to the fire department’s top position of fire chief in 1994.

The Ocoee resident died Sunday, Feb. 23, at Health Central Park, in Winter Garden, at the age of 65.

Dollar was employed by the Winter Garden Fire Rescue Department for 27 years. Working with the department was his passion, second only to his family, said his wife, Glenda Dollar. His daughter, Amanda Williams, recalls him often coming home from work with stories to tell.

In his first 10 years, Randy Dollar — in addition to being a fire inspector — served as a firefighter, lieutenant and captain. He was a division commander for one year before being promoted to assistant chief in 1985, and his tenure as fire chief ran fro 1994 until his retirement in 2002.

When Randy Dollar was diagnosed with multiple sclerosis in 1995 at the age of 41, he continued to work as long as he was able.

“He had a very big heart for the people, and it was absolutely devastating to him when he received the MS diagnosis and he (eventually decided) to resign because he couldn’t walk,” Williams said. “He said they needed a whole person and he wasn’t a whole person anymore.”

Glenda Dollar also remembers him making the tough decision to retire.

“He was very heartbroken when his health came to the place that he had to go on a walker,” she said. “He told me one day that he just didn’t feel that it was right for him to keep that position. He said that he had always felt that whatever he asked of the firemen, he himself would do. And he said at that time that he wasn’t able to do that stuff anymore.”

Glenda Dollar said he was disappointed because he had a list of projects he wanted to complete before he left the position.

Matt McGrew, Winter Garden’s current fire chief, recalls his first visit with Randy Dollar about five years ago — and he said he was thrilled to be able to “talk shop” about the fire department. The two stayed in close contact and had many good conversations.

“Every time … he always wanted to tell the next story,” McGrew said. “He was really proud of his time with the fire department. That’s probably what meant the most to him — the fire department.”

McGrew said Randy Dollar’s legacies are the fire station that was built on Palmetto Street while he was chief and his dedication to safety. He oversaw the transition of the department from a combination of full-time and volunteer firefighters to all full-time employees, as well. His leadership was evident.

Then-Assistant Fire Chief Randy Dollar, far left, with the department.

McGrew was thrilled after finding a folder — tucked in the back of a file cabinet — that included Randy Dollar’s project wish list and was eager to share the news with him.

“That made his day to find out that much of what (Randy) wanted to see happen, Chief McGrew wanted to see happen,” Glenda Dollar said.

“He’s a thinker, and he had a plan with the department,” McGrew said. “He had the same vision as I do for the fire department. … He was hard-working. He was very methodical. … He knew how to talk to the city officials. He knew how to respect them and to try to get what we needed.”

As the disease progressed, Randy Dollar’s body continued failing. He spent the last four years living at the assisted-living facility Health Central Park.

 “Everybody who knew my dad, they would come in and say, ‘That’s the smile, the million-dollar smile,’” Williams said. “He was the greatest. Everybody thinks their daddy is the best, but God bless him, he’s my hero.”

The week before her father died, Williams filled a shadowbox with all of his WGFRD badges and presented it to him.

Randy Dollar's daughter, Amanda Williams, made him a shadowbox with all of his fire department badges just before he died.

Another prized possession was a scrapbook of photos and newspaper clippings put together by a niece.

“Every time he went out on a call, you said a little prayer that he would be safe,” Glenda Dollar said.

He returned home from his shifts with some emotional stories. When their children were young, Randy Dollar was called to a fire involving a mother and young child living in a recreational vehicle.

“He just came home and hugged his children,” she said. “It hurt him to go somewhere where a child had been hurt in a fire. … That was just his calling in life. That was Randy. He was a helper.”

Battalion Chief Brian Sanders was a young volunteer firefighter when he met Randy Dollar in 1987. He recalled his gentle but authoritative demeanor.

“He was always pleasant and always kind, and then when it came time to be more of an administrator or put his foot down, he did,” Sanders said. “That’s what I liked about him.”

One memory will always resonate with Sanders — how professionally and respectfully Randy Dollar handled the aftermath of the deadly tornado that hit the city in 1998.

“I want to mimic that style,” he said.

After the chief had retired and was confined to his house, members of the fire department drove the brand-new tower truck, not yet in service, to the Dollar home.

“We knew he couldn’t come to the fire station to see it,” Sanders said. “He was blown away that we did that. … We knew how much that was going to mean to him. … That was just one small thing we could do for all the things he had done for us and the fire station.

“He cared about the Winter Garden Fire Department tremendously,” he said. “It’s your family.”

Randy Dollar was born in Winter Garden, Florida, in 1954 and graduated from Lakeview High School in 1972. He married the former Glenda Brimer, of Ocoee, in 1976; the couple celebrated 43 years of marriage and had two children, son Michael and daughter Amanda, as well as four grandchildren.

A celebration of life is planned for Saturday, March 7, at Evolve Church, 10564 Second Ave., Ocoee. Visitation is from noon to 1 p.m.; the celebration begins at 1 with refreshments to follow. For those who wish to do so, donations to help with end-of-life expenses can be made at

Randy Dollar, left, and a fellow firefighter at the previous fire station on South Boyd Street, which is now the SoBo Art Gallery.


Randy Dollar, a 27-year veteran of the Winter Garden Fire Rescue Department, enjoyed a Christmas morning operating a scaled-down version of his department truck.


Amy Quesinberry is the community editor of the West Orange Times & Observer and the Windermere Observer. She was born and raised in Winter Garden, grew up reading the community newspaper and has been employed there as a writer, photographer and editor since 1990....

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