All-Too-Early Guide To The Orange County Mayor’s Race In 2018


    By Jacob Engels


    We recently detailed the rumors that former Orlando Police Chief and current first lady of the Orange County Sheriff’s Office Val Demings is likely to pass on what very likely would have been a successful run for the Mayor’s office in 2014.


    We here at the East Orlando Post are prepared to call this one for Mayor Jacobs assuming this proves to be true.


    So now, we are going to list the top 10 candidates for the mayorship in 2018.  Five are Republican, five are Democrat, and none have made any affirmative statements of their desire to run.  This isn’t about who will win, its about who could.  We will also add two that are probably thinking about it but have zero chance.


    Finally, we don’t include gadflies in this list.  Matt Falconer has some redeeming qualities, but I see no benefit to including him here because he cannot and will not get past 50% of the vote.  He, at best, will steal votes away from Republicans in the primary, which could shape what Republican, if any, advances to the general election… but we are totally confident it won’t be him in the general election.


    So here they are… the All-Too Early Field for the Orange County Mayorship in 2018:




    Linda Stewart

    The county commissioner turned mayoral candidate turned state rep is rumored to be contemplating a run for the vacated Clerk of Court office in 2014. 


    Pros: High name ID.  Well liked by the Sentinel.  Good work ethic.  If she’s the Clerk of Court, she’ll be on the ballot in 2014 and 2016, meaning her ballot ID would be unmatched county-wide.


    Cons: Could well lose her house seat if she chooses to run for reelection this time, considering her close win last time with the Obama wave against a guy that lived in Tampa.  Not a great fundraiser, and was particularly bad at it during her mayoral run.


    Scott Randolph

    The state rep turned county democratic chair/tax collector has a position to run from and the grassroots on speed dial.  Recent discussion about getting rid of the tax collector’s office in the charter boosts speculation he’ll run.


    Pros: Everybody who pays taxes in Orange County writes a check out to “Scott Randolph”, helping with name ID.  Orange County is increasingly blue and he’s the chief democrat.  His resignation to run, properly timed, would spur a special election for tax collector, and that would help his turnout because democratic turnout would likely spike.


    Cons: There are questions about whether as blue as Orange County has become, whether they really are ready for a liberal firebrand married to an even more liberal firebrand. Tends to make enemies, and those enemies will be ready for this. White male makes for a tough sale with the left, left wing crowd.


    Darren Soto

    The democrat representative turned senator of Puerto Rican descent is a Tallahassee up and comer.


    Pros: A Puerto Rican lawyer with a reputation for moderate politics and crossover appeal might be the secret.  Will be six years into his senate career, meaning the timing will be about right.  A practicing lawyer, he would augment his already considerable fundraising skills.


    Cons: Rumors abound that Soto is looking at statewide office.  Leaving the Senate with time left for a crowded field may be a tough sell.  Also rumored to be a leading candidate for the Orlando Mayor’s office should Dyer move on.


    Val Demings

    Could very well win this time, but her husband’s possible ambition to run for congress may cause her not to run. 


    Pros: The telegenic, highly credentialed former Orlando Police chief is compelling for a lot of reasons.  Being married to the sheriff doesn’t hurt for fundraising or Name ID, and leads to some good volunteers.


    Cons: She is probably missing her best matchup opportunity this time.  Sheriffs tend to decline in popularity over time, meaning the value of her brand is likely to decrease.  Sheriff Demings would stand a significantly better chance of winning a congressional seat in a presidential year, but would then have to not run again, meaning the brand could take even more abuse.  Sheriff Demings loss for congress seals her political fate as not ever holding this office.


    Robert Stuart

    The gregarious Orlando City Commissioner is a presumed successor to Mayor Dyer, but Dyer’s decision not to run for Governor combined with him raising the Orlando Mayor’s salary gives the mayor a look of a man in for the long haul, meaning Stuart may test the waters in the county.


    Pros: A family name that’s worth six-figures in an open mayor’s race.  A reputation for moderate politics.  Deep roots in old Orlando that would translate to quick support.  Running a respectable campaign could well position him for the Orlando Mayor’s race down the road.


    Cons: Doesn’t have a position on par with the other four in terms of profile.  Everyone knows he wants to be Orlando Mayor, so there are fire-in-the-belly questions.  White male.


    Barely Honorable Mentions –


    Relevant democrat players not likely to make a dent: any democrat school board member, Senator Geraldine Thompson, any of the other democrat reps, Commissioner Moore-Russell or any of the other constitutional officers




    Andy Gardiner

    Florida’s incoming senate president has Orlando roots and a mayoral look.


    Pros: Likely to have seven figures in soft money contributions to dole out from his senate presidency.  Liked by the Orlando Sentinel.  Positive relationship with the Disney/Universal/Sea World triumvirate goes a long way.


    Cons: White male.  Lacks a signature accomplishment at this point after 13 years in the legislature, although he certainly can change that as senate president.  Propensity for delving into social issues could erode support in key constituencies.  Many believe he has some agreement with Dan Webster to vacate so he can take over in 2016 or 2018 (Webster is currently 64 years old, meaning he will be 67 when Gardiner terms out).  May or may not have any relationship with the development community.


    Ted Edwards

    The Orange County Commissioner and lawyer has two stints on the commission and a good rapport with the business community.


    Pros: Has the support of uberHotelier Harris Rosen.  Has a conservative, pro-growth record on the commission.  As a partner in Foley and Lardner, he has a national fundraising base.  Well liked in development circles.


    Cons: White male.  Relationship with Rosen brings with it several enemies.  Questions about whether amusement parks would be comfortable with such a close Rosen ally being so powerful.


    Scott Boyd

    The county commissioner from West Orange won a decisive upset six years ago.


    Pros: Telegenic.  Respected by development community for fairness.  Good fundraiser.  Well liked by the amusement parks, many of whom he represents.  Very popular in the business community. Campaign would likely be managed by John Dowless, who ran Mayor Jacobs successful race.  The only candidate on this list from West Orange County, which is voter rich and historically votes in a block.


    Cons: White male.  Mayor Jacobs is from the western portion of Orange County, meaning two consecutive mayors would come from the same district. 


    Marco Pena

    The impressive but unsuccessful state house candidate scored a major coup by getting appointed to Orlando’s road building agency.


    Pros: Former UCF student body president and trustee can fundraise from that base.  Florida Hospital executive won’t hurt with money either.  Puerto Rican Republican pretty much alone in that space among people who are elected or who belong to major government entity boards.  Outperformed the district in a campaign that had Obama turnout.  Only viable candidate from eastern Orange County.  Assuming Soto doesn’t run, Pena is the only candidate of either party of Puerto Rican descent.


    Cons: Didn’t get off to a great start on OOCEA board by angering mayor and board chairman.  Would need to become chairman of the board and would have to continue tradition of cleaning up authority to have the gravitas and credibility to run, and neither of those are a given.  Would need the state attorney investigation to turn up nothing.


    Sandy Adams

    The former 4-term state rep and one-term congresswoman resides in East Orange County.


    Pros: Above average name ID.  Detailed record of service, and a state and national fundraising base.  Tough campaigner used to being the underdog.  Photogenic, with an extremely compelling life story.


    Cons: No evidence that she has ever been interested in local government, having served in state and federal government during her ten years of elected service.  Would need to ramp up her focus on fundraising and build relationships with the development community.


    Relevant Republican Players Not Likely to Make a Dent: Any of the other state reps, school board members, and county commissioners.





    Jennifer Thompson

    The Queen of Slime.  Criminal Commissioner.  Sunshine Law Violator Extraordinaire.


    Pro: Legally qualified to run for mayor.


    Cons: Shady.  Not very bright.  Been accused of a crime by the state attorney.  Picture Teresa Jacobs with 30 fewer IQ points, a bigger ego, a lousy reputation and a recently minted “sunshine law” rap sheet.  I kind of doubt she even gets reelected this time but we will see.  A pawn of lobbyists.  No achievements to talk about… large or small.


    Bill Sublette

    The chairman of the Orange County School Board and perennial candidate for congress, Orlando mayor, state house, school board, etc.


    Pro: He has a title that sounds like it could run for the mayor’s position.  He is one of the most ambitious people in Orange County, having run for Florida house, senate (in 2000 before switching to congress), congress (losing to Ric Keller as a huge favorite), Orlando Mayor (losing to Dyer) and now School Board Chair.


    Cons: This guy wants to run for everything and never wins.  I don’t dislike him, but I generally recognize that his ambition makes him think about running for everything but he never wins if there is even the slightest bit of an opponent.  White male.   School board members aren’t known for their blockbuster fundraising.




    So there it is, five democrats and five republicans who would likely create the field for the most powerful position in local government in central Florida.  What do you think?


    Jacob Engels, is the Founder of East Orlando Post. Along with the Post, he owns several other businesses and is currently enrolled at Valencia College. Jacob has lived in Avalon Park since it’s founding and enjoys playing with his black Labradoodle Jasper, listening to indie rock, and seeking out new business ventures. He can be reached at