Latest prediction for the Gateway District elections in 2020

Posted on September 07, 2019, 11:36 am
12 mins

Welcome to the weekend!

Weekends normally mean a lower number of readers on this website, but those who are here on Saturdays and Sundays are typically the most avid readers. So it’s a perfect time to do a 2020 election update!

As the Democrats continue sorting out who’s who in terms of their primary election to see which candidate will challenge President Donald Trump next year, individuals considering making a run at local offices are also starting to put plans together and strategize as well.

In terms of the Gateway District elections, the seats occupied by Chairperson Margaret Fineberg, Supervisor Ed Tinkle and Supervisor Kathleen Flaherty will be up for grabs in November 2020. Vice-Chairman Bill Guy and Supervisor Doug Banks were both re-elected in 2018 and their seats won’t be contested until 2022.

Let’s begin with the incumbents and whether they’ll be a factor in 2020.

At the top of the pecking order, we begin with Fineberg.

Fineberg was re-elected in 2016 despite the fact she did not campaign. At all. Not a single flyer, lawn sign, personal appearance or anything. Some may have viewed it as a sense of confidence on her end, but I viewed it as a sign of insecurity. She wanted to be able to have a built-in excuse if she lost.

Fineberg has not announced if she’ll run again in 2020. I predict she’ll do the same thing: file to run, fail to campaign and see what happens.

Turning to Tinkle, he’s the only Supervisor who’s announced his intentions for 2020 – and that is not to seek re-election.

Honestly though, I think there’s a 50% chance he reconsiders and runs again. If he comes out after seeing this article and stresses “I’m NOT running” then I’ll believe it. But for now, despite his declarations that he would be a single-term Supervisor, I think the door at least remains open.

Finally, Flaherty.

I think she’ll run again. And if she does I think she’ll fight hard and compete to win. She’ll campaign relentlessly and prove to the community (and frankly, to herself) that she deserves her spot on the Board of Supervisors.

Several months ago I would have written Flaherty off completely, but I think the winds of change may be blowing and she now actually may have a chance to be re-elected, which I’ll explain later.

Moving on to potential challengers.

The only person we know with 90% or above certainty will be running is Flavia Walsh from Magnolia Lakes.

Walsh attends the district meetings is regularly engaged in Gateway’s issues, particularly the ponds. While I realize “ponds” don’t exactly sound exciting, they are the biggest problem from a financial standpoint in the Gateway community.

Walsh would enjoy widespread support both in Gateway and Pelican Preserve, meaning she could probably unseat the candidate of her choosing whether it was Fineberg, Tinkle or Flaherty.

On the opposite end of the spectrum, there was one person I thought was likely to run, but now I think there’s literally no chance he will – and that’s Rob Spicker of Daniel’s Preserve.

Spicker would have been a tremendous add to the Board of Supervisors, but after leaving WINK News he joined the Lee County School District in their communications department. So for one, he probably doesn’t have the time to sit on the Gateway board with his new job; and two, I don’t think the school district would look too favorably on it if he did. While I haven’t asked him, I’m 99% sure we can rule Spicker out for 2020.

In the middle of the will-they-or-won’t-they spectrum are a handful of candidates.

A few names I’d put right at 50% or greater would be Bob Geppert of Pelican Preserve, Rod Senior of Gateway Greens, Warren Davies of Stoneybrook and Jim Brann of Hampton Park.

Keep in mind that I haven’t spoken to any of these potential candidates about any of this … so what you’re reading is purely my analysis. While my record is 100% accuracy when it comes to the elections themselves, at this point it’s way too early for me to be saying that any of this is anything more than speculation for entertainment purposes. In no way am I vouching that anything I say here will become reality.

I’m just spit-balling. EVERYTHING said from this point forward is just for fun.

Good? So let’s go.

Pelican’s leaders won’t look too favorably upon candidacies by Tinkle, Brann or Senior meaning any of the three would have an uphill climb to win if they ran.

All three of them have expressed strong support for revoking an agreement between Gateway and Pelican Preserve which basically says “Gateway pays for Gateway stuff. Pelican pays for Pelican stuff. They’re separate.”

While much of the noise has centered around the amenities such as the soccer fields, the reality is that the Board of Supervisors’ approach to the Lake Bank Restoration Project has got Pelican Preserve residents and leaders asking Whiskey Tango Foxtrot is going on in Gateway.

Pelican’s board has taken a cost-conscious approach to repairing problem ponds in that community. Gateway’s leaders have take an aesthetics-first, money-is-no-object approach which as resulted in probably 1,000% (not a typo) higher costs in Gateway to fix the same problems that exist in Pelican.

The Gateway trio above have said “Wouldn’t it be GREAT if we could stick Pelican residents with the costs of our most-expensive-plan-in-the-world (not a typo) approach?” whereas Pelican’s leaders who have taken a far more modest approach are saying: Your approach is absolutely crazy. And we’re not paying for your crazy.

For this reason, I believe Geppert will run for Tinkle’s seat and Pelican will file to run a candidate for Flaherty’s seat as a contingency plan. Pelican may withdraw one or both candidates depending on what happens, but they’ll want someone at least qualified to run for Flaherty’s seat in case Senior or Brann runs for it.

Ah, but last time Senior ran for Supervisor it was against the sitting chairman of that day, Pete Doragh. Won’t Senior want to run against Fineberg?

He may.

But I now believe Walsh will run against Fineberg because Flaherty will fight like hell for the job while Fineberg won’t. Why not take the path of least resistance? Not to mention that any unexpected opponents would prefer to target Flaherty rather than Fineberg. So why wouldn’t Walsh prefer a one-on-one battle with Fineberg instead of a 3, 4 or 5-way race for Flaherty’s spot?

Besides if the Pelican block knows that Guy, Banks, Geppert and Walsh are all Supervisors, they probably won’t care who’s in the fifth seat and let the chips fall where they may for Flaherty’s seat.

So if Walsh does take on Fineberg, that leaves Flaherty’s seat as the sole remaining option and I think Senior, Davies and Brann may all take a run at it.

Brann learned his lesson that fighting against Pelican is a losing battle. Senior literally wrote me an email and said “Yeah I purposely chose not to run against Pelican” (which was smart, and Senior won as a result of that choice) back in the day.

Only one person has ever defeated a Pelican-backed candidate: meFlaherty.

It would take an all-out effort to unite the Gateway block to ensure an election win, and right now of the candidates and incumbents listed I can only see that happening for Walsh. If Tinkle chose to run again and said “I don’t like Rule 6 (the split spending rule) but you have my word I’ll let it stand” that could change things as well. I’m not saying Geppert wouldn’t target that seat anyway, but that rule is the largest obstacle in the way of any of Tinkle, Senior and Brann winning anything ever again when it comes to GSCDD elections.

Not trying to knock on those guys. Just offering my straight-up analysis.

As I’ve watched more Stoneybrook Advisory Committee meetings lately I’ve become increasingly comfortable with Davies as a possible Supervisor. The only problem I’d have is that he seems to know right from wrong and does push back slightly, but then when he’s confronted with the choice of either having to rock the boat or accept “wrong” he tends to just accept “wrong”.

He’s a smart guy but if he’s not going to stands up for what he seems to know is the right thing then what’s the point of having him as a Supervisor?

So here’s my September 2019 prediction of the next Board of Supervisors who I BELIEVE will be seated for the first time in December 2020 after the November election, taking Tinkle at his word that he’s not running again:

Chairman Bill Guy
Vice-Chairman Doug Banks
Supervisor Bob Geppert
Supervisor Flavia Walsh
Supervisor Kathleen Flaherty

If Tinkle runs again and promises to leave well-enough alone between Pelican and Gateway, I suppose that that could change things. But other than that, I think the above list is what you’re looking at for 2020.

Editor of the Gateway Sun and owner of restaurant delivery service Florida Food Runner.

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