Phil Anderson leaves mayor's job with legacy of shaping city's future

The mayor, who will hand off the title this week to Sheila DeCiccio, took a few minutes recently to reflect on his time in office

April 5, 2024

By Beth Kassab

Phil Anderson came into office in the spring of 2021 as the tumult of a global pandemic took the lives of thousands of Orange County residents and upended commerce from New York’s Wall Street to Winter Park’s Park Avenue.

For months at the start of his term, the City Commission was still meeting via video. Shops and restaurants struggled to bring back customers. And uncertainty hung over the markets that affect the city’s key streams of tax revenue such as real estate and new development.

Now three years later, as Anderson prepares to turn over the gavel on Wednesday to new Mayor Sheila DeCiccio, the city just hosted the 65th Winter Park Sidewalk Arts Festival packed with hundreds of thousands of people and at least four new commercial development projects are in the works.

“When you look at where we were coming out of COVID, it’s remarkable,” Anderson said. “We finished three years later with a lot of initiatives started or in progress.”

Anderson said millions of dollars in federal American Rescue Plan Act funds played a major role in smoothing the city’s recovery.

But then, about halfway into Anderson’s term, the city confronted another historical challenge when Hurricane Ian dumped more than a dozen inches of rain on the region and caused record flooding in Winter Park and beyond.

As a result, the city is now taking the first steps toward drainage projects that DeCiccio has highlighted as a major priority.

Anderson’s term also saw the purchase of the 18-hole Winter Park Pines Golf Course, which this year turned a small profit, according to financial documents; the opening of a more than $40 million Library & Events Center and the start of construction on Seven Oaks Park.

He also led some policy initiatives such as a long-term effort toward renewable energy at the city-owned electric utility, voter approval of charter amendments that require a supermajority on the commission for certain zoning changes and a plan to expand the Community Redevelopment Agency.

“I ran to really make life better and to keep the charm of our neighborhoods and the downtown in tact,” said Anderson, a civil engineer whose career eventually lead him into finance and development. “And I think we did that.”

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Mayor Phil Anderson presents Mary Daniels with the Mayor’s Founders Award at the 2024 State of the City Address.

The most recent financial reports show the reserve fund at more than $20.5 million.

While the day-to-day operations are led by City Manager Randy Knight, the mayor plays a large role in setting both the agenda and the tone of the public meetings.

At his final meeting in March, Anderson reflected on his time on the dais and the sometimes contentious comments from residents who would show up to speak for or against policies or projects.

“I want to thank everyone who has stepped up to the mic to speak,” he said. “We may not always agree, but this is what America’s about.”

Listening to those comments, he said, was one of the most rewarding parts of the job.

For example, residents of west Winter Park played a significant role in changes to a proposed rental development known as Winter Park Commons. The project, which will replace a now vacant church in the historically black neighborhood, will have more single-family homes and fewer townhomes as a result of people showing up and speaking out at the meetings.

“It’s amazing,” he said. “It does make a difference. Sometimes it doesn’t seem like it makes a difference, but over the long run it does.”

Anderson made a habit during meetings of summarizing in real time what he was hearing from fellow commissioners or speakers as a way of building consensus and and steering the debate. And he rarely lost sight of the fact that not everyone in the commission chambers understood the history or nuances of every policy measure, often pausing to provide context or demystify the discussion for everyday residents who stopped in — in person or via live stream — to watch their local government in action.

Jeff Briggs, longtime planning and zoning director, shared a story at Anderson’s final meeting that also captured his penchant for connecting with residents.

Anderson, like many mayors, is often asked to appear at community events. And one morning in Central Park he was giving the opening remarks before the start of a 5K. After he spoke, the DJ was supposed to play the National Anthem before the race started.

But a technical failure resulted in silence.

“There’s this dead pause and then the mayor says, ‘Well, I can sing it!” Briggs recalled.

The former high school choir member of son of Southern Baptist missionaries — his dad was a minister of music — led an acapella rendition of the anthem.

“I happened to have a clear voice that morning, which doesn’t always happen, and I thought, you know, if I start low enough I think I can do this,” Anderson recalled. “There were probably 200 people who started singing it with me.”

For now, there are no new singing gigs in his future. When Anderson’s term officially ends on Wednesday he said he plans to spend more time with his wife, children and grandchildren as well as his parents, both now in their 90s.

“I’m hoping I can find the right path to continue to serve the city,” he said.

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