So, Who’s Actually Going to Win? Key West Insiders Predict the Race for Mayor

We may not know until late Tuesday night, but everyone is trying to figure out just who might triumph in the hard-fought race for mayor of Key West.

While a previous story revealed how some voters secretly felt about the choice before them, this time we turned to the people in the know: people in the innermost rooms of decision-making, people often asked to play political pundit, and even some who have emerged victorious from races of their own. Plus, for good measure, a top tarot card reader.

They were asked not necessarily who they want to win, but who they think will win the highest office on the island and why.

Most participants asked not to be named in order to preserve professional relationships and avoid appearing to tell anyone how to vote. No one was aware of who else was participating in this story. Neither campaign was asked to respond to the individual predictions, which were solicited as forecasts rather than allegations or endorsements.

These are the forecasts.

Change Will Win

Sam. I think people really are looking for a change in this seat. It'll be close, though. The Commission needs a leader willing to question the items on the agenda and the budget. Sam has proven that he's inquisitive, and not afraid to speak up instead of going with the flow.

Dee Dee is pleasant, but her campaign hasn't been. The political machine behind her has not done her any favors. Had they focused on issues instead of character assassination, they may not have alienated as many voters.

Again, close race but I think change will win.

– a longtime resident and well-connected business owner

The Quiet Voters Will Decide It All

A 367 vote difference. Kaufman for the win. It is going to be down to the wire. People are not talking about their vote, it's really a well kept secret. It's almost as if saying who you are voting for is asking for an argument. A few people are screaming, but the quiet voter is the one that the ballot is listening to. It's totally up to just a few silent ballots. If it's more than 500, I'm shocked.

– a former candidate for a Key West election

The Pissed-Off Voter

My guess would be Sam Kaufman prevails as the winner of the mayor's race. And I base that upon a local history and a national history. The local history being the electorate is very pissed off right now at all the shenanigans that have been going down at City Hall. And the current administration, the mayor, amongst others, has thwarted many an opportunity to make realistic corrections so that it doesn't happen again. And that's got the people really pissed off.

The fact that there's been a surge of funds into [the mayor's] campaign coffers by people who would benefit from keeping the current mayor in office leads me to believe that they fear they're going to lose. If they didn't think they were going to lose, they wouldn't have that sudden massive infusion of cash into her campaign.

If we look at it on a national level, we see this has just played out in some primaries where candidates who are receiving massive infusions of cash for their campaigns have lost against low funded campaigns. And it's the same scenario. So that leads me to believe that Kaufman has a good chance of being victorious in this race.

– a winning campaign manager

The Slate vs. The Street

In my experience, negative campaigning has never worked in local elections because people kind of see through it. But this election, unlike any other election, has had more negative campaigning. And it's hard to know if people are going to blame the candidates or blame their people who sometimes get a little bit too carried away in trying to advance their candidate.

It's interesting that a lot of the big money interest in Key West seem to choose a slate. And the people that are not happy and want to see change, there's another slate, but there are two slates. It's not like there are individual races. It's like this slate or that slate.

I always think it's more wise to run your own campaign and not be caught up in being part of a slate of candidates. But the chamber obviously endorsed a slate. That is the slate. That is their business-friendly, big money slate. It seems like the big money in town and the chamber coalesce around the same slate. And the little people and the people that are angry about where the island is going, they outnumber those people, but will they vote?

I think they're going to go for the mayor.

– a Monroe County-wide elected official

Sometimes You Vote for the Human

Right now there is a major backlash against the extremes of the Republican Party. And that could impede other people on the ticket who aren't on the extreme fringes of the party. Keep in mind, in the circular hemisphere of politics, the corporate Democrat and the centrist Republican are kissing cousins.

Coming back to the middle is not the worst thing. There's an expression in, of all places, Germany that's called the Golden Middle. Some of their leaders would've done well to look at that, but we are that as a nation and as a community. And whether we see it in the fractious elements of a campaign, it's kind of not that important. In the bigger, longer span, Key West has always reinvented itself.

I grew up with a straight party ticket. My father was very successful as a writer, but he was a textbook definition of a raging liberal. I'm not hiding that. It's part of my background. I understand that pathos.

But my grandmother, my grandfather, my cousins, my aunts, many of whom were, as you would say in the Midwest, a righteous Republican. So I'm both. All of that runs through me. All of that is part of who I am. And that's why I say two things can be true at once. And I think why I support Mayor "DeeDee," for mayor of Key West, is because I simply see from those Midwestern roots of mine, a decent, caring human being. I don't see a lot of darting and flashing in those eyes. I see openness and a relatable human. And sometimes that's what you have to go with. And there's more to that obviously in this case, but fundamentally that's what compels [voters].

DeeDee will win.

– a cultural insider with broad ties across the island community

Watching the Crowd, Not the Candidate

Mostly, what I'm using to determine what I believe the outcome will be is the activity surrounding the candidates, not the candidates themselves. The activity and the people that support them. In the early part of the campaign, it seemed more like it [leaned] Kaufman.

Either one that does win, it's going to be close. I guess if I had to choose who I believe would end up winning, it's probably Sam. Just because he got out there early, and I believe that he's got a lot of people snowed.

– a widely recognized community figure with extensive local and institutional knowledge

Look to the Cards

For this next entry, I switched things up and contacted the longtime islander and celebrated tarot card reader Ron Augustine, who can be found at Mallory Square's Sunset Celebration most evenings. He has read for celebrities, inspired characters in novels, and been covered in national press.

Ron, instructed me to select six cards, after shuffling the deck, with the first three for Henriquez and the final three for Kaufman. The spread went as follows:

Henriquez: Eight of Wands (upright), Five of Swords (reversed), The Sun (upright)

Kaufman: The Fool (reversed), Strength (upright), Three of Pentacles (reversed)

Almost immediately after turning over the final card, Ron called it for Mayor Henriquez.

"I think she's going to get it."

"She's got the eight of wands, which shows that things are working for her. Things are going on her behalf. Things are moving in this direction very quickly. The Five of Swords shows me that she is very flexible mentally, which I think is important. But, she has The Sun card upright, which shows that probably a lot of local people back her. And I think that's where her strength lies.

"Now with him, he has The Fool reversed," Ron said of Kaufman's spread.

"He has the Strength card upright and he has the Three of Pentacles reversed. So the full reverse shows me there's a lot of fear on his part. He's afraid. He has certain fears about this situation. It's a lot of things here that are getting in the way of a good start, moving in the right direction."

"Strength card – he's got a lot of support by all the important people, but I don't think that's enough because then he has the Three of Pentacles reversed, which shows me that there are certain things that he doesn't know. And it's what he doesn't know that's going to hurt him in this race."

Ron also admitted that while he stands by his interpretation of an Henriquez win, the presence of The Sun card for her, and the Strength card for him, means it could be anyone's game.

"She has all of the down home [voters] , the people that really matter here, the salt of the earth, the family. She's got that behind her. He has strength, which shows me all the important people are behind him in some way."

And The Predicted Winner Is. . .

Taken together, these predictions just about tilt in favor of Kaufman.

Nearly everyone expects a close race, and even those arriving at the same candidate got there by very different metrics: overwhelming negative feelings toward City Hall, campaign organization, quiet voters who aren't showing their hand, money, personality, and of course, what people are hearing around town.

Nobody seems entirely sure what Key West is about to do. And none of the people who spoke for this story would be that surprised if the outcome proved them wrong.

By late Tuesday night, they’ll see, if they even care, just how good they are at reading the room. Who do you think will win?