Race To Replace Teresa Jacobs Begins

The individuals gunning for Mayor of Orange County.

By Jacob Engels

After years in public office, some people should know when to return to private life while others should rightfully continue representing the people.

Becoming the next Mayor of Orange County after nearly a decade of sub-par leadership from Teresa Jacobs is a huge undertaking, a responsibility that will take an immense amount of dedication and intestinal fortitude.

Early on, there are clear front-runners for the job. We have covered this topic before, dating back to 2013 and most recently in the final months of 2016.

You get the point, so mark the end of my rambling introduction to the idea of a new Mayor in 2018. On to the legitimate or illegitimate (depending on your politics) candidates seeking the post.

Orange County Commissioner Pete Clarke

Pete Clarke led the vanguard for the New Dawn of the GOP in Central Florida shortly after being elected in 2012, working to stifle human trafficking perverts and embrace our LGBT brothers and sisters with important human rights ordinances.

A veteran of the healthcare industry and an elected official who embraces a low-key approach, Clarke would be hard to bring down if he decides to run for Mayor in 2018. His fiscal diligence and logical embrace of open-mindedness on social issues is a dangerous combination.

It’s not rooted in some far-left ideology, but in his faith. Clarke is a Christian who believes we are all created equal and is not ashamed of his belief.

Better yet, he is not bought and paid for like many other “candidates” for this post. Clarke has even stood up to top donors when he feels their development projects are too much or their requests too broad.

While I do not agree with all votes cast by Clarke, his dedication to the best solution for Orange County residents resonates with people like myself and other voters.

To cap it off, he is an extremely talented musician, slaying with his Low Bid Band at popular locales. IF he decides to run, Republicans would be hard-pressed to find a better candidate.

Property Appraiser Rick Singh

Anytime a constitutional officer garners 1,000 plus people to their annual “State of the County” address, rumors are going to swirl about possible bids for higher office. Orange County Property Appraiser Rick Singh has dwarfed the attendance numbers posted by Mayor Teresa Jacobs for the second year in a row.

During his time in office, Singh has saved the county millions and refused to curry special favor with Disney executives who wanted him to “adjust” his standards when appraising their properties. His most recent opponent in 2016 survived entirely on donations from Disney-linked groups and individuals.

Singh was able to count Republican mega-donor David Siegel in his corner and at the same time, earned support from progressive corners like local unions and party activists as he steamrolled his way to victory against Edward DeAguliera last November.

Judging from his previous fundraising figures, Mr. Singh would easily be able to raise $1,000,000 in 60 days or less. He could be the only candidate on the Democratic line that has a shot at peeling away large enough numbers of Republican votes to win on the first ballot.

Singh is set to finish his term in 2020, meaning he would have two years before the next mayoral election, assuming he does not run in 2018. If he announces, expect a hyperbolic response from the old guard in Orange County. To them, Singh is a self-starter immune to their soul-selling ways. He doesn’t trade power for wealth as so many elected officials are ready and willing to do.

Philanthropist & Former Commission on Homelessness Chairman Andrae Bailey

Man, does he have a knack for self-promotion, but not the type that is exclusively beneficial to himself. Mr. Bailey has charisma and puts that energy to work for causes beyond his own self-interest.

Young, attractive, and well-dressed, Andrae Bailey has the following to organize a serious bid. He is liked by Democrats and Republicans alike, enjoying support from both Orlando Mayor Buddy Dyer and Republican State Representative Mike Miller.

His greatest strength? Understanding the power of digital media to evangelize for a cause. If elected, he could be the most savvy locally elected official in the entire United States.

That’s if we don’t lose him to a something before then.

Orange County Tax Collector Scott Randolph

When Mr. Randolph was elected, many worried he was “too progressive” to operate in an impartial manner. A former member of the Florida State House of Representatives, he was known for being a political bomb thrower.

But something shined on Randolph after he was elected to succeed longtime Tax Collector Earl K. Wood. He modernized the office and slashed the budget better than the most vocal fiscal conservatives in our state.

This led to short wait times, lower costs for services, and larger reimbursements for Orange County than any other Tax Collector before him. After the Mayor and her lackeys tried to usurp the power of Randolph and other constitutional officers in Orange County, they formed a united front to fight back and won multiple court battles.

Randolph has the best of both worlds, a strong connection to the progressive base and respect from those across the political spectrum for his tightwad approach. We saw impressive renovations to longstanding offices and the opening of new locations – without living outside our means. Wait times dropped like a rock and appointment by text is now a thing.

Plus… how adorable is he on Facebook as Scott the Dad or Scott the Husband?! A good father, supportive spouse, and honest public servant… triple threat!

Wildcard Candidates – Will They Commit?

Real Estate Ace Dean Asher

The 2016 Florida Senate candidate can raise money like none other and that alone makes him a serious contender.

Asher valiantly took on shit-for-brains Linda Stewart in the campaign to replace State Senator Andy Gardiner in Florida’s (insert district)  last year in the heavily democratic seat.

He came up short, but the deck was stacked. The Orlando Sentinel has worked since then to “soften up” Asher who is the heir to a very successful real estate empire which has served Central Florida for decades.

Like Clarke, Asher is a pro-equality Republican who can carefully navigate the progressive left and conservative right to form a strong bi-partisan coalition. His post on the Greater Orlando Aviation Authority has given him a high profile which has educated him on the ins and outs of local politics.

Look at the numbers from his Senate race and you will see that Asher has a clear path to victory in a countywide race. If he wants to take another foray into politics, this could be his best shot. He is a worker and gifted retail politician.

Timeshare Mogul David Siegel

Westgate CEO David Siegel has been laser-focused on helping Orange County and the state of Florida address the rising heroin crisis after his daughter, Victoria Siegel, overdosed in 2016. His wife, socialite Jacqueline Siegel, has been rumored as a potential candidate for Governor, but her husband’s role might be more local in 2018.

After decades of wielding his power as a top-level donor to both Republican and Democrats in local elected office, Siegel certainly possesses the personal finances and favors to call in if he wanted to mount a campaign. He is an old man, yes, but the tragedy that struck his family has given him a relatable way to communicate with the electorate in Orange County.

Tens of thousands of families struggle with addiction in their families, a plague affecting the wealthy, middle class, and poor alike. Mr. Siegel has a compelling stump speech and a blank check to match.

His motivation, however, lies in the fact that he can’t count on current leaders to address the overdose epidemic, no matter the number of zeros he can guarantee for their re-election bid. The only way to ensure proper funding for overdose combating emergency medicine and proper education programs is to hold the office of Mayor.

Siegel has the name recognition to become Mayor but like so many other successful entrepreneurs, he must decide if he wants to accept the restrictions of holding an elected office. I argue that his need to spare any other father from the suffering his family has endured at the hands of overdose and addiction outweigh any misgivings he might have about campaigning for Mayor.

Planned Parenthood / Equality Florida Leader Anna Eskamani

The progressive fire-starter is no stranger to political dogfights and is quite possibly the most vocal unelected progressive leader in Central Florida and the state at large. She helped raise millions in the wake of the Pulse terrorist attack in the summer of 2016, became an adjunct professor at her alma mater (UCF), and joined the board of the League of Women Voters.

Eskamani’s proximity to Florida’s progressive fundraisers and top operatives would make her a serious contender in the fundraising and grassroots department. A social media effort to draft her into the race went live earlier this week and has already garnered quite the buzz among progressive voters in the area.

Orange County Commissioner Emily Bonilla

In a mayoral campaign that is estimated to feature up to a minimum of seven contenders, Bonilla also has a much lower win number to get through to the general election than she is likely to have in a 2022 race. And 2018, if history is any indicator, could be very good to progressive candidates like Bonilla, from the Commission all the way up to Congress.

We first reported this possibility for Bonilla this week, read that here.

Her ability to build on this anti-development energy RIGHT now for a 2018 bid might be the best shot she has to accomplish her ultimate goal of stopping development into the remaining open land in Orange County.

Screw being sidelined by a bunch of politicians with their hands stretched out to developers for campaign cash. Bonilla could stand for the average, everyday citizen facing a new way of life as a result of continued development and home-building

Winter Park Mayor Steve Leary

Top donors and backers of Leary have been encouraging the Winter Park Mayor to consider a bid for Orange County Mayor or possibly throw his hat in the ring for the GOP nomination in Florida’s 7th congressional district. So far, his time as Mayor has given Winter Park residents a lot to be thankful for.

Leary pushed incentives for homeowners who were considering adding their residences to the historic registry, the successful renovation of the Winter Park Golf Club, a Winter Park Health Foundation backed community wellness program, and no mileage or rate increases.

His gifted fundraising skills would allow Leary to raise hundreds of thousands with ease in a countywide race. Leary is also one of the most active and well-liked citywide elected officials in Orange County and could be the only candidate with a relevant executive role in both the public and private sectors.

The Orange County Mayoral campaign will develop over the next few months and the Central Florida Post will be there along the way to provide updates and in-depth coverage. Onward to 2018!


Jacob Engels is an Orlando based journalist whose work has been featured and republished in news outlets around the globe including Politico, InfoWars, MSNBC, Orlando Sentinel, New York Times, Daily Mail UK, Associated Press, People Magazine, ABC, and Fox News to name a few. Mr. Engels focuses on stories that other news outlets neglect or willingly hide to curry favor among the political and business special interests in the state of Florida.