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Castillo Commission 8-6-2025

The city commission’s “gotcha game” needs to end

The city commission’s “gotcha game” needs to end

By Linda Grist Cunningham, editor and proprietor

Linda Grist Cunningham is editor and proprietor of Key West Island News and KeyWestWatch Media LLC. She and her husband, a park ranger at Fort Zach, live in Key West with their Cat 5s.
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08/16/2025

During the Key West City Commission’s morning session on Aug. 8, Commissioner Aaron Castillo all but came out of his seat in frustration over the bickering and posturing — I call it the “gotcha game” — that’s become a regular feature of commission meetings. “It’s just overwhelming,” he said, arms extended wide. “It’s gotta stop.”

I was snarling similarly from my comfortable seat watching at home. I wish the city had a “like” button on its live streams because I’d have smashed it about a dozen times. Castillo lost it 2 hours and 12 minutes into the session, after Commissioner Sam Kaufman’s minutiae-laden posturing and grilling of interim City Attorney Kendal Harden about the process for recruiting and hiring a new city attorney.

Kaufman is notorious for declaiming from the dais, reminding folks of his long tenure and extensive knowledge of city government and poking and prodding staff — and particularly the city manager — often with questions asked and evaded or already asked and answered. He’s always said he does that to ensure “transparency,” though much of the time it feels like a sophomoric gotcha game. Kaufman had already run one on the city manager earlier in the meeting, so it’s understandable (at least to me) that Castillo erupted.

“We get up here and beat these issues,” he said in his 4 minute and 44 second scolding. “We got a selection committee. … If we aren’t going to rely on who we appoint to do a job, then what are we doing here? I mean this is getting ridiculous. Every time we get up here, we’re going over and over the same thing. We need to move forward. … Every issue there’s a beat-up on the agenda. … It’s too long an agenda to be nitpicking every issue that comes before City Commission.

“I’ve had it with the nitpicking on the dais,” he continued. “That’s why the public doesn’t respect us up here. They don’t respect us because we don’t respect ourselves. … I selected somebody for the city attorney selection committee. We need to honor what they tell us.

“These meetings are like the Gong Show,” he said. “This is ridiculous. City manager, city attorney, tell us what you need. Let us give it to you, but I’m not going to sit up here and go over and over and over this. It’s too overwhelming for me.”

Me, too, Commissioner Castillo. Me, too.

But wait. Gong Show? You’ll have to be older than dirt to catch the reference to the TV show that debuted in 1976 and featured performers judged by audience applause or a panel of judges who bonged the gong if they didn’t like what was onstage. Go ahead, check YouTube; you’ll find it.

gotcha game
Commissioner Castillo vents his frustration over “beat downs” during commission meetings.

Key West “gotcha game” is getting out of hand

Shortly after Castillo wound it in, City Manager Brian Barroso, enthusiastically bouncing in his seat, began his report with this: “Buckle up, listen up. This is what we call in the business a tease. We’re teasin’ it,” Barroso was excited, really excited or really, really excited 18 times in 15 minutes. I’m not sure what the “it” was.

That’s pretty much what commission meetings have become. The audience boos and hisses, claps and curses. There are so many rolling eyes and smirks on the dais and among the staff and in the audience, it’s a wonder contorted faces don’t fall off in fatigue by the end of meetings.

Then there’s the endless testosterone-fueled grudge match between City Manager Barroso and Commissioner Kaufman. They lie in wait for each other to make a misstep, push each other’s buttons, then pounce with smarmy voices and pretend obsequiousness, determined to shove each other aside as king on the hill. Gaad, they love mansplaining things to each other. These two need an intervention with some lessons in collaborative engagement, because if they don’t get their working relationship on track, the whole city suffers.

Meanwhile, the rest of us gotta sit by, heads down, looking at the ceiling, scrolling our phones and checking the time.

This city commission is by no means the only fractured mess I’ve covered over 40-plus years. Key West commissioners are egged on by a surging number of grassroots partisans, conflicting politics, ill-supported conspiracy theories, potential mayoral candidacies and wildly complicated governance issues, ranging from criminally corrupt former employees to a crumbling infrastructure and the chaos of federal and state mandates.

I have the privilege of writing about commission decisions, the ones I agree with and the ones I don’t. I respect the extraordinarily difficult row commissioners hoe. Theirs is a tumultuous job unlike any previous commissioners have faced. I know tempers flare and the temptation to one-up each other is relentless.

But Commissioner Castillo is spot on. This Gong Show has to stop and that’s got to start with Kaufman and Barroso.

1 Comment

  1. Demetria Danielides

    I hope that our Commissioners are in agreement that they all should be involved in some professional coaching-The events they have endured can take a toll for each of them to try and do what’s right. It’s obvious with their behavior. I believe they each are trying to do their daily best yet should reach out for daily professional advice.

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