ORLANDO, Fla. (FNN NEWS) – If you’re like many Orlando politicos, you’re aware of the Orlando City Council race that has been getting attention since 2014 in Orlando City Council District 5. In 2014, now Orlando City Councilwoman Regina Hill (below) successfully and surprisingly unseated four-term community staple Daisy Lynum…well she annointed her son Juan to carry on the Lynum legacy …but… that plan crumbled like an over cooked cookie. (In fairness, it’s important to acknowledge that I helped on the Hill campaign as a volunteer.) With that acknowledgement, I am still amazed this particular race is already heating up as the Commissioner seeks re-election. But why exactly are so many that can’t even vote in the district interested in its players and outcome? Well, it comes down to the Commissioner’s personal life, the unique group of nontraditional opponents she has and why they are suggesting they can unseat her.

City of Orlando District 5 Commissioner Regina I. Hill. (Photo courtesy of her Facebook page)

Almost as soon as Commissioner Hill was elected, some familiar faces predicted her doom and suggested everything from removing her from office to asking her to resign. Commissioner Hill illustrated to all during her initial campaign bid, and after getting into office, that she is a fighter and is willing to go the extra mile for her constituents.

Sadly, however, some of the Commissioner’s challenges slowly entered into her newly elected position. Nearly immediately, her aide was involved in turmoil after a drunken interaction at a local movie theater. Then came the rumor the Commissioner was removed from a comedy club for being drunk and disorderly. It would not be long until the Commissioner’s children were involved, and ultimately exonerated, from drug trafficking allegations. There were even questions over whether her home actually was in the district. If all that wasn’t enough, sadly her daughter was murdered while visiting Tallahassee, taking the Commissioner from being a grandparent to a parent again overnight. But outside of the staffing issue, these issues are all part of her personal life.

We all have struggles and ups and downs, so while it might be popular to point out these challenges as the bases to want to see someone new in the office…not so fast.

You see, one thing I learned while working on the Commissioner’s campaign in 2013 was that District 5’s constituents have a unique perspective to how they vote for and support candidates and those in office. What might traditionally be a disaster for a candidate or elected official in another area of town didn’t seem to matter as much to District 5 voters. I recall a gentleman stopping me the night of Hill’s watch event in which she learned she made it into a run-off with Commissioner Lynum’s son, Juan Lynum. Somehow the gentleman got on the topic as to whether the Commissioner’s past glances with the law, 21 of them to be exact, would interfere with her chance of winning. I remember his response to this day: “Randy, you need to understand something. Being black and living in Parramore is something you’ll never understand. We all know someone that’s been touched by drugs, crime or by the law. It’s a way of life there. Regina is going to win this race.”

Commissioner Hill was eventually elected indeed defying all traditional logic. Not because she hadn’t worked hard or because we were tired of a career politician–certainly both points entered into the equation–but District 5 decided that her history and brazes with the law didn’t matter in ways most of us would think it would. You won’t find a candidate that works any harder. That said, let’s now explore the candidates in the race to unseat the one-term Commissioner and the likelihood of their efforts.

ERICKA DUNLAP

Ericka Dunlap (photo courtesy of her Facebook page)

Ericka Dunlap is most known as the first black Miss Florida and the 2004 Miss America. Dunlap grew up in the community of Carver Shores in a family with deep roots in the community. Her father, who passed away a few years back, owned a family roofing business. I met Dunlap in 2013, ironically just around the time I was introduced to Commissioner Hill. Their backgrounds couldn’t be more different.

Dunlap is a Boone High graduate and a graduate of the University of Central Florida, which is when she cut her teeth in the pageant world also being crowned Miss Orlando. Many don’t realize this, but the difference between Miss USA and Miss America is that the Miss America Pageant is heavily weighed on talent. It just so happens Dunlap has the brains and beauty to match her ability to sing ….wait for it … country music. I originally contacted Dunlap when I was launching a domestic abuse fundraising and awareness program, “Walk a Mile in Her Shoes,” for Harbor House, a local shelter and safe haven for women, men, children and pets in Orlando. Dunlap had recently returned from Nashville where she unsuccessfully attempted to launch a career in country music. Divorced and looking to reinvent herself, the timing was ripe to come home to Orlando and kick start her life again. While working with Dunlap to promote the domestic abuse awareness event, I recall our discussion about whether she might one day run for office. Dunlap’s family had a substantial history with the Lynum family, so she said “someday,” suggesting her loyalty to the Lynum family was more important than running for office against them.

I remember our visiting with Orlando Mayor Buddy Dyer during our tour promoting “Walk a Mile” and his hope to somehow find a fit for Dunlap, at the time, possibly as an Ambassador for the University of Central Florida. I mean, think about it: hometown girl graduates from UCF, wins Miss America, comes home to help her alma matter. You couldn’t ask for a better story. My prediction, at this stage of the process with Dunlap now an announced candidate supported by the Bracey legacy, the Mayor would really love to see Dunlap in the role of Commissioner. So while I’m unaware of any “official” endorsement, whether quiet or announced, you can be assured the Mayor is certainly a fan of Dunlap. It’s clear, as well, that Dunlap is off to a nice start in fundraising, which doesn’t necessarily translate to a win, but certainly doesn’t hurt.

JIBREEL ALI

Jibreel Ali (photo courtesy of his Facebook page)

My observations of Ali come at a distance from various interactions and political discussions on social media. His arsenal, or “secret weapon” in this race, rests not with him, but his family. He is the grandson of the former City of Orlando and Orange County Commissioner Mable Butler. Butler, royalty in local politics, continues to be a driving force in the community, most recently working to develop an affordable housing project in the Washington Shores community with her name on it, “Butler Preserve.” Ali has been utilizing his grandmother, in various social media videos, in which they talk about the history of the community and his running for office. But that’s not all he has working for him, as his mother-in-law is long-term Orange County School Board member Kathleen “Kat” Gordon. Gordon too has a long legacy of working hard for her community and certainly carries family clout to the race. Uniquely, however, Gordon has been relatively silent on her son-in-law’s inaugural entry into politics. Ali’s biggest challenge, in addition to fundraising, thus far seems to be his inability to put out clean and clear communications pieces.

Ali came out quickly to point out Dunlap’s lack of direct connection to the community in the very first District 5 forum a few weeks back, possibly tipping his hat too soon as to his strategy to trip the former beauty queen. Uniquely, during the same debate we saw a quick reaction from Dunlap towards Ali and others, including the current Commissioner, regarding their attack. She may be a former Miss America, but I’ve also witnessed the receiving end of her direct tone. Don’t anyone get it twisted, Dunlap too is a fighter and clearly ready to put on the boxing gloves when push comes to shove in running for this office. Remember, she’s a fierce competitor and skilled in public relations.

CYNTHIA HARRIS

Cynthia Harris (photo courtesy of her Facebook page)

Harris comes into yet another run for this seat quiet and a bit timid. While she seems to gain some attention, my observation of her in 2013-14 and now remains the same: she simply doesn’t seem to be able to provide deep rooted solutions to her suggestions of the district needing more jobs and affordable housing. While that messaging might resonate for any community, I think the debate last week made her inability to compete with the other players pretty clear. She simply doesn’t have the bandwidth to be competitive and probably would be better suited to align with one of the other candidates if she truly wants to be part of unseating Commissioner Hill.

SO THOSE ARE THE CANDIDATES. WHY THE INTEREST?

Chardwick Hardee, Vice Chairman of the Orange County Republican Executive Committee, recently told FNN News: “People love their community. And Districts 1-6 are all part of the community. No community rises when one falls. Therefore the success of District 5 is important to all of Orlando.” While Hardee, a former candidate for Orange County School Board, makes a point, there’s also the sheer drama of the race as it plays out on Facebook that draws attention.

National FOX News commentator and political strategist Tezlyn Figaro, who was Hill’s Director of Communications on her first winning campaign is so far not supporting any one candidate. Yet, she has created a Facebook page that lights up occasionally with unexpected drama, “Orlando City Commissioner D5 race commentary.” Originally created for political strategist and communication commentator discussions, the page has quickly morphed into a place where people are, at times, heavily debating the race. Not surprisingly only the incumbent seems to feel the page is worthy of discussion, which I believe is a fatal mistake on the part of Hill’s opponents. The Lynums made the same mistake in 2014 regarding social media, ignoring it as an influencer, leaving many of us and Commissioner Hill the open field of controlling the narrative to her benefit.

Not everyone is excited about Commissioner Hill heading towards a reelection bid and have made it no secret. Recently, a video of a clearly inebriated Hill surfaced and was shared frequently with the hashtag “#ResignReginaResign.” Yet, when you go back to my original analysis and discussion of how the Commissioner won in 2014, even with her baggage, will the anger of some be enough to keep her from reelection? Hill lost most of her support base, as related to key campaign volunteers, after being sworn in. Many felt she quickly sold out to the establishment and became known for not returning phone calls or communicating with those that got her elected. Then again, at least for me, I never expected much in return. Some believed there might be financial gain from her being in the office. But as I understand it, few if any saw financial benefits in the form of contracts and such.

The fascination with this race comes from so many different angles, but here’s the most obvious draw: It’s like a reality show without the cameras. You’ve got an outspoken no-holds-barred Commissioner with a record, the beauty queen with an edge, the family legacy candidate, and then some other folks who so far can’t find a way to be very memorable. It’s no secret unseating an incumbent is tough work. Commissioner Hill, despite her personal ups and downs, has been very public in the work she has done for her district, utilizing social media like a pro. The Commissioner’s personal challenges aren’t keeping her from fundraising either with a steady and notable stream of contributions coming her way.

Additionally, District 5 has the new Orlando City Soccer Stadium, the new Orlando Magic nighttime entertainment venue as well as a push for more affordable housing, so it’s of great importance to everyone who lives in Orlando, but especially in District 5.

While it’s far too soon to make a prediction on what the outcome will be of the November 7th election, if Commissioner Hill’s opponents don’t quickly define and separate themselves from why they are a better choice than her, my thoughts are Commissioner Hill wins maybe outright. If Dunlap or Ali can pull Hill into a run-off, one of them will win. November is a lifetime away in politics, so anything is possible. It’s much easier to determine who loses than who will win this one with possibly as few as 2,000 votes deciding the Commission seat. Grab your popcorn and adult beverage folks. This is going to be an interesting race to watch over the summer and into the fall.

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Randy Ross is a political contributor for Florida National News. | news@floridanationalnews.com