Sheila DeCiccio to run for Winter Park mayor

Sheila DeCiccio to run for Winter Park mayor

Sheila DeCiccio to run for Winter Park mayor

Jason Johnson announces run for DeCiccio’s remaining term

Oct. 3, 2023

By Beth Kassab

Winter Park Commissioner Sheila DeCiccio announced this week she is running for mayor, triggering a special election for the remainder of her term that has already attracted at least one contender: local attorney Jason Johnson.

DeCiccio, who was elected in March to a second commission term without opposition, said she will make improving the city’s infrastructure and preserving Winter Park’s small town feel the central focus of her campaign.

“We’ve made great headway, but there’s still a lot to be done to maintain the heart and charm of the city,” she said. “Hurricane Ian laid bare a lot of our problems such as pipes that need maintenance, brick streets that need attention. Infrastructure is the No. 1 issue and we can’t kick this can down the road anymore.”

She pointed to the water basin studies ordered by the current commission and priorities set out in the transportation master plan, including more bike paths and extending sidewalks, as foundations for taking the city to the next level.

Winter Park is a city manager form of government, which means Randy Knight oversees the day-to-day operations of the town of about 30,000 people and a more than $200 million budget. But the mayor and commission hire the city manager and set policy and the mayor can be highly influential when it comes to driving an agenda or steering debate, particularly at public meetings.

DeCiccio, who moved to Winter Park more than 40 years ago after working as an assistant district attorney in Massachusetts, became the first woman partner at the Lowndes law firm in the 1980s. She went on to practice law with her husband, Dan, at DeCiccio & Johnson and has served on the city’s Planning & Zoning and Code Enforcement boards. The couple has two adult children.

She was first elected to the City Commission in March 2020 as the world was shutting down because of the COVID-19 pandemic. Then two years later as the pandemic finally eased, Winter Park experienced some of the worst flooding in its history as Hurricane Ian brought record-level rain across the region.

She said those tumultuous events have sharpened her focus on keeping the city financially strong and prepared for the next emergency.

“We’ve learned from all of it,” she said. “That’s why infrastructure is my No. 1 priority.”

Mayor Phil Anderson, who is not seeking a second term, said he supports DeCiccio’s campaign and wants to see the long-term planning he helped initiate as mayor carried forward.

Mayor Phil Anderson gives the state of the city address earlier this year as commissioners Marty Sullivan, Sheila DeCiccio and Kris Cruzada look on.

“I supported her in her first election and we really got to know each other,” Anderson said. “I’ve continued to enjoy working with her as she runs for and hopefully serves as mayor.”

So far, DeCiccio is the only candidate to announce for the March 19, 2024 election, though the official qualifying period for the ballot isn’t until December. In order to run, she announced she would resign from her commission seat on April 10, the date she would take office as mayor if she is elected.

That means there will be a special election for the final two years of her three-year term as Seat 2 Commissioner.

Jason Johnson

Jason Johnson, candidate for Winter Park City Commission, with wife, Lori, and daughter, Molly.

Jason Johnson, an attorney in the Winter Park office of the Byrd Campbell law firm, announced this week he will run for the seat. He is a first-time candidate who has lived in Winter Park for 13 years with his wife, Lori, and their daughter. He is also chairman of the city’s Board of Adjustments, which rules on homeowner applications for building variances.

“My north star in all of this is to preserve the charm of Winter Park, but I’m also a rule-of-law guy and I recognize that landowners have rights and due process exists,” he said.

Johnson is the only announced contender for the seat. Justin Vermuth, also an attorney, said he explored the idea of running but told the Voice this week he does not plan to enter the race.

The qualifying period for candidates to enter the contests for mayor and the commission seat ends Dec. 11.

Questions or comments? Email the editor at

To comment or read comments from others, click here →

Commission mulls asking voters to approve more debt to pay for flood prevention

Commission mulls asking voters to approve more debt to pay for flood prevention

Commission mulls asking voters to approve more debt to pay for flood prevention

Winter Park Playhouse, Bank of the Ozarks purchase remain in limbo while the City Commission works to balance $200 million budget

By Beth Kassab

As they attempted to balance the city’s budget, Winter Park City Commissioners on Wednesday floated the idea of asking voters to agree to take on more debt for three new programs — flood prevention, upgraded public safety buildings and the acquisition of more park land. The city’s more than $200 million budget has a shortfall of at least $30 million for projects desired by the commission.

The first of the bond referendums, which will ask voters to approve borrowing money for specific purposes, could show up on the ballot as early as March 2024, though a specific timeline is still unclear.

Mayor Phil Anderson indicated a top priority is repairing and enhancing the city’s stormwater management system, which was overtaxed with severe flooding in the wake of Hurricane Ian.

“Our residents want to have a really good flood prevention system,” said Anderson. “We’ll probably have to come forward with a capital bond issue for $20 million worth of stormwater improvements.”

But the city is still awaiting consulting reports about what kind of work needs to be done and how much it will cost — a process that is likely to extend into next year.

Vice Mayor Sheila DeCiccio expressed frustration that commissioners are being asked to assign dollar figures to projects without yet knowing the true costs.

“It’s hard for me to work on the budget without having an engineering report on stormwater,” she said. “I don’t have a clue what figure to plug in … I’m frustrated because I don’t know where to go from here.”

Anderson suggested the city begin by prioritizing $2 million for work in various neighborhoods that city staff already know is critical.

DeCiccio noted that up to $14 million is set aside in the city’s Community Redevelopment Area fund to buy the Post Office — a purchase the city has sought for years in order to expand Central Park, but without success because the U.S. Postal Service is not interested in selling. With the CRA set to dissolve in four years if Orange County does not approve an extension, that money could be used to fix flooding problems on the west side of the city or other priorities, several commissioners agreed.

Commissioners will devote a public meeting in August to specifically hash out the CRA budget.

For now, they remained non-committal on other items such as setting aside money to help the nonprofit Winter Park Playhouse find a new home or the acquisition of the Bank of the Ozarks property on Orange Avenue to expand Seven Oaks Park.

Commissioners left the dollar figure next to the Playhouse line item blank in hopes that $4 million or more from Orange County’s Tourist Development Tax would come through, though staff noted it could be well into 2024 before the county approves grants of that size for local arts and culture groups. The local theater is set to lose its current lease on Orange Avenue next year.

The board also discussed whether to purchase the vacant land owned by the Bank of the Ozarks to augment the new Seven Oaks Park and some expressed support for a special bond referendum to raise money to help the city acquire more park space.

No decision was made and it’s still not clear whether a purchase of the Ozarks land is possible or if the owner, who refused the city’s first offer, wants to sell.

“My crystal ball is cloudy,” said Commissioner Marty Sullivan, who has tried to orchestrate a deal on the property in recent weeks.

The other large unfunded project on the city’s wishlist of capital projects also remained up in the air: a new $18.5 million downtown parking garage.

Anderson suggested transportation fixes, specifically $700,000 in technology enhancements, could negate the need for more parking and a new garage. He said commissioners will know more about that after the Transportation Master Plan is discussed.

Commissioners also expressed interest in acquiring property on S.R. 436 near the 7th hole of the Winter Park Pines Golf Course, which the city bought last year, to provide space for a restaurant along the lines of The Taproom at Dubsdread. The popular eatery at the city of Orlando’s Dubsdread Golf Course in College Park appears to be the inspiration for how Winter Park envisions developing the golf course and adding another revenue stream to the mix.

“For it to be first class like the Winter Park 9, then it’s going to need that property,” said Commissioner Todd Weaver, who zoomed into the meeting from a sailing trip.

The owner is asking about $2.6 million for the property.

“This could make a lot of money,” DeCiccio said. “Could we get a business case on this?”

City Manager Randy Knight said staff will bring back more details for review.

When it came time to set the city’s property tax millage rate, Sullivan and Weaver made a brief attempt to raise the millage by a quarter mill or about $75 a year for the owner of a house with a taxable value of about $300,000.

“We’ve been diving into how much money we’re going to need and it looks like either we are going to have to cut some things we really feel we need or we’re going to have to raise the millage rate,” Sullivan said, adding the move would allow the commission flexibility between now and when the final budget is adopted in September.

But Anderson, DeCiccio and Commissioner Kris Cruzada said the millage rate should stay the same, particularly after Knight reminded the group that it recently approved higher fees for residents for everything from park services to stormwater to garbage collection.

“We raised our user fees,” Cruzada said. “I don’t know if we want to go double-barrel and also raise the millage … The Fed raised interest rates another quarter point today. If we move forward to bond, it’s going to be a higher interest rate. It’s a reflection of the time we are living in and residents and homeowners are feeling it. I just want to be sensitive to that.”

DeCiccio and Anderson noted that strong property values along with new construction to be added to the tax rolls will continue to boost city revenues while keeping the millage rate the same — at least for the time being.

Questions or comments? Email the editor at

To comment or read comments from others, click here →

Karen Castor Dentel announces run for elections supervisor at luminary-filled Ruth’s List event

Karen Castor Dentel announces run for elections supervisor at luminary-filled Ruth’s List event

Karen Castor Dentel announces run for elections supervisor at luminary-filled Ruth's List event

Gen Z Congressman Maxwell Frost and State Attorney Monique Worrell headlined the event at a Winter Park home to support women candidates

By Beth Kassab

Orange County School Board member Karen Castor Dentel said Friday night she will run for Supervisor of Elections next year as Bill Cowles retires from the position he’s held for more than 25 years.

Castor Dentel, who made the announcement at a Ruth’s List fundraiser in Winter Park, said she is drawn to the position because of the “current state of politics” and a desire to push “clear communication with voters and educate them about the process” amid a national landscape littered with misinformation.

Cowles, who was first elected in 1996, said in February that he will retire when his term ends in early 2025.  So far Castor Dentel is the only person filed to run in the race that will be on the November 2024 ballot, according to the supervisor’s website.

Karen Castor Dentel

She was one of a handful of candidates who announced races after U.S. Rep. Maxwell Frost, who represents Winter Park in Congress, and Orange-Osceola State Attorney Monique Worrell talked about why more candidates are needed to combat what Worrell called “an unprecedented time” as “democracy is slipping away.”

“It’s been a rough couple of weeks,” Worrell said amid chuckles from the crowd gathered around a pool deck overlooking Lake Maitland.

The comment was a reference to criticism from Gov. Ron DeSantis, who said her office was negligent because she didn’t prosecute a man for a misdemeanor marijuana charge in 2021. That same man is the suspect in a triple shooting in February that killed a 9-year-old girl, a woman and a Spectrum News 13 reporter.

Worrell said mass incarceration will not build a stronger society and she questioned DeSantis’ claim that he presides over the “free state of Florida.”

“I submit to you that Florida is not free,” she said, noting that DeSantis and a “Legislature beholden to their dictator” have pushed new restrictions to what K-12 students can learn about gender identity, made it easier for Florida, which has the highest number of Death Row exonerations, to execute people and passed a ban on most abortions after six weeks.

Worrell, a mom to three boys, revealed that when she was 39 years old she became pregnant with a daughter she had “waited for my whole life.” But when she was 10 weeks along her doctor told her that tests revealed the baby was unlikely to survive.

She had to make a decision about whether to continue or end the pregnancy.

Ultimately, she said she decided to continue the pregnancy and delivered a baby girl who died just three weeks later.

“If I had to make that decision again I would possibly make a different decision,” she said.

Worrell, who gave birth to her youngest son about a year after her daughter’s death, said she shared the deeply personal story for the first time because she knows the toll restrictions on reproductive freedom can take on women and families.

“It’s an insult to call Florida free,” she said, noting the importance of Ruth’s List, which helps elect Democratic women who are in favor of abortion rights.

Ruth’s List was founded in 2008 by former state chief financial officer and gubernatorial candidate Alex Sink. The organization, which has raised $7.5 million over 15 years, is named for Florida Congresswoman Ruth Bryan Owen — elected in 1928 just eight years after women gained the right to vote.

Frost, known as Gen Z’s first congressman elected last year at age 25 to represent greater Orlando, including Winter Park, Maitland and the UCF area in east Orange County, said Ruth’s List is crucial in supporting progressive candidates.

He said he took an interest in politics at age 15 “because I didn’t want to get shot in school” in the wake of the Sandy Hook Elementary School massacre in Newtown, Conn.

“Generation Z … we truly are the mass shooting generation,” Frost said. “… We need to elect politicians who will see the world through the eyes of the most vulnerable.”



To comment or read comments from others, click here →

Do You Vote by Mail?

Do You Vote by Mail?

Do You Vote by Mail?

Don’t delay – request your ballot today!

by Anne Mooney / January 4, 2023

A new law, enacted last April, has changed the Vote by Mail (VBM) process, requiring all voters to submit a new request to the Orange County Supervisor of Elections for a VBM ballot.

The Supervisor of Elections office must receive your request no later than 5:00 pm ten days before the election.

Winter Park Election Day is March 14, 2023

This means the deadline for submitting your request for a VBM ballot is March 4, 2023. But don’t wait until then.

You can request a VBM ballot any time

You can request a VBM ballot as soon as right-this-minute (during business hours), so don’t wait. Here’s how – it is so easy.

Online – Go to  In the orange banner at the top of the main page, click on “Voters.” About half-way down the dropdown menu, you’ll see “Vote by Mail.”

There, you will find thorough, easy to follow instructions for requesting a VBM ballot.

Fax or Email – On the same page, you will find instructions for downloading a VBM Request Form, which you can print, fill out and submit either as a photo attachment by email, by Fax or by snail mail.

No Computer? No Problem

Call the Supervisor of Elections office and speak to a live person, who will process your request on the spot. The number is 407-836-8683.

People in the Supervisor of Elections Office are there to help. They are courteous, knowledgeable and they actually answer the phones. We Orange County residents are truly fortunate

To comment or read comments from others, click here →

Charter Amendments Win Big

Charter Amendments Win Big

Charter Amendments Win Big

by Geri Throne / March 9, 2022

Winter Park voters sent City Hall a clear message Tuesday: They want the city commission to be more cautious in approving major zoning and land-use changes.

Voters approved all six amendments to the city charter by an average of more than 20 percentage points. The biggest vote-getter on the entire ballot was the sixth amendment, which requires an additional hearing if a proposed ordinance or zoning change is significantly changed while under consideration. That amendment drew 4,351 votes for approval – more than 62 percent.

The other five amendments will require 4-1 supermajority votes to approve land-use changes involving wetlands, public land and certain density increases. The charter results heartened supporters, who see them as essential for protecting the city’s character. Opponents had argued that the amendments will create overwhelming barriers to development.

Weaver and Cruzada prevail

Voters also re-elected Todd Weaver to a second term over political newcomer Elijah Noel, the only candidate to oppose the charter changes. Weaver won by more than 10 percentage points – 3,885 to 3,139.

In the much closer Seat 3 race, Kris Cruzada beat Anjali Vaya by less than four percentage points – 3,579 to 3,305.

The city’s modest overall 31.6 percent voter turnout bested other Orange County municipalities with elections Tuesday. Neighboring Maitland had a 14 percent turnout.

More Winter Park voters cast their ballots by mail than in person. Mail-in ballots alone did not decide any race or issue, but they widened margins in some cases. Weaver, for example, was ahead by 75 votes until early voting and mail-in votes increased that margin to 746.

Speaking to more than 100 supporters at Mead Gardens on election night, Weaver said he was happy with the results. He apologized for his role in “a rift” that had developed because his supporters were split between Vaya and Cruzada, who ran on similar platforms. Weaver, who had backed Vaya, called on his supporters to get behind her “the next time she runs.”

A disappointed Vaya wasn’t ready to talk about a next time following the vote tabulation. She said she would continue her service to the city as a member of the CRA advisory board.

Cruzada credited supporters and his family for helping him win his close race. He expressed hope that more new candidates will step forward to run for the commission in the future.

Elijah Noel could not be reached for comment Wednesday.

To comment or read comments from others, click here →

Charter Amendments Win Big

Vote This Tuesday!

Vote This Tuesday!

by Geri Throne / March 6, 2022

With Election Day two days away, 16 percent of Winter Park voters have voted by mail or cast early ballots in the municipal election.

That’s a higher percentage than the four other Orange County cities holding elections this week, but not by much. It amounts to 3,627 votes out of Winter Park’s 22,635 registered voters. More than 19,000 voters still need to be heard from on Tuesday.

Two commission seats and six city charter amendments are on the Winter Park ballot.

For Seat 4, incumbent Todd Weaver faces political newcomer Elijah Noel. In the Seat 3 race, entrepreneur Anjali Vaya faces attorney Kris Crusada.

The six charter amendments deal with certain development decisions. The first five would require a supermajority of 4-1 votes to approve: 1) the sale of city-owned property; 2) the rezoning of parks and public lands; 3) rezoning of lakefront property to higher densities and intensities; 4) rezonings or comprehensive plan changes that would increase existing residential density and intensity by more than 25 percent, and 5) the development of wetlands. The sixth amendment would require an additional public hearing and reading of an ordinance if a substantive change is made during the adoption process.

Polls will be open from 7 a.m. to 7 p.m. on March 8. Voters must go to their assigned polling place with photo and signature identification. If you requested a mail-in ballot and did not use it, bring the mail-in ballot to the polls with you.

To comment or read comments from others, click here →