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Key West city manager

Key West city manager | Bubba Uprising? Tired of being disrespected

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.


Before I drag out “Mary, Joseph and the Wee Donkey,” let’s get this on the record: I get my news about Key West City Manager Al Childress from the same places most of you do: whatever local news headlines come my way and gossip along the Coconut Telegraph.

I do recall wondering, when Childress was hired in April 2023, whether his big city (South Florida) experience, which looked great on paper, would mesh well with island time and Key West’s complicated and nuanced small-town Conch culture. Fourteen months in and looks like the answer might be “not so much.”

And not unexpected either. No community responds well to outsiders who come in with a to-do list that starts with “Here’s how we did it where I come from” even if said ideas might be good ones. It takes a lot of listening and learning to understand the culture of a community and few outsiders are willing to do that. Instead, they just want to get going on their remake.

I’m an outsider. We bought our home in 2008 and permanently moved in in 2012. I’m never going to be a locals’ local. But I think I know this much: There’s a growing sense across the island of “We’re being disrespected by outsiders who move here — and promptly want to change everything.”

Back to “Mary, Joseph and the Wee Donkey.” What the heck is going on in City Hall? Because whatever “it” is — and I’m betting there is a bucketload of “its” — it doesn’t bode well for the island.

Earlier this week word leaked to local news media that a couple of city commissioners wanted Childress fired. By midweek four of six commissioners confirmed they were on board with terminating his four-year contract even if it cost taxpayers upwards of $100,000 in severance. Two days before the “fire Childress” coup, Assistant City Manager Todd Stoughton resigned to spend more time with his family, which is often a euphemism for “I can’t take this anymore.”

The City Commission has scheduled a 2 p.m. meeting on June 26 at City Hall to discuss and possibly act on forcing Childress out.

Key West city manager
Fort Zach | Summer Solstice | June 20, 2024

Key West city manager | Follow the sitemap

You’ll need a sitemap to follow the drama. Aligned against Childress are outgoing Commissioners Jimmy Weekly, Clayton Lopez and Billy Wardlow. Likely with them is Lissette Cuervo Carey, who is the only one of the four who will remain on the commission after the August election. Sam Kaufman, who will also remain, hasn’t made his position clear. Mayor Teri Johnston and Mary Lou Hoover support Childress. Johnston is leaving and Hoover continues on the commission.

On Aug. 20, Key West likely will have three new commissioners, a new mayor, no city manager, no assistant city manager — and possibly four failed bond referendums totaling $300 million. Only Kaufman, Hoover and Cuervo Cary will remain. Because they were unopposed, former Key West Police Chief Donie Lee replaces Wardlow in District 3 and former Monroe County Tax Collector Danise “DeeDee” Henriquez becomes mayor.

Even if you gave up figuring out who’s on first, that kind of political drama isn’t healthy. What makes it worse is it’s playing out in a vacuum of facts and context. The best we get are undocumented references to “low morale” among city staff and employees, Childress’ failure to understand both island time and a small town’s ways of doing things and a vague sense of long-standing, dysfunctional, unending internal conflict among elected and appointed officials and employees.

Key West city manager | 3 things we can do

So what do we do?

  • First, let’s take a deep breath. Step back from the tea-leaf reading. This chaos is nasty, but we don’t have a clue to what precipitated this week’s headlines. In that, Kaufman’s “I don’t have the facts yet” position makes sense.
  • Second, demand transparency and specificity from the mayor, commissioners, Childress and, yes, city employees. Airing employee failures and conflicts in public is a traumatizing exercise, but hanging a termination on the likes of “low morale” and “he doesn’t get us” exacerbates public distrust. There’s a big difference between a boss who demands I do my work on real time, not island time, even if I’d rather not and one whose management style deliberately creates a hostile work environment. So, which is it?
  • Third, attend the June 26 special meeting. I don’t hold out great hope for learning much. The current commissioners and mayor rarely get into anything resembling real discussion, much less conflict, at their meetings. While I appreciate their decorum, I’ll admit I’m often left wondering exactly what led each one to vote a particular way. Again, that lack of transparency thing. Still, a public meeting is better than the backroom conversations most assuredly taking place right now, Florida’s Sunshine Law notwithstanding.

I can’t tell you who’s in charge down at City Hall. With so much turmoil and so many short-timers, probably no one. I’m also thinking there are a lot of Conchs and long-time locals who are fed up with outsiders disrespecting them. It’s not political; it’s cultural. Call it the Bubba Uprising. Welcome, DeeDee and Donie. You’ve got your work cut out for you.

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  1. Ronald Zemlicka

    Great reporting as always Linda. Based on my 20 years of living in Key West as “an outsider “, it appears to be Deja Vu all over again.

  2. Ronald Zemlicka

    As usual, very well written. You know I lived in Key West for twenty wonderful years as “ an outsider”. Based upon my experiences and observations I could share stories and tales, some true and some, well, who knows.. However, my opinion, and just my opinion since I don’t have any facts, is that it’s Deja Vu all over again.

  3. Joseph Bement

    All those who were on the hiring committee should also GO…..What were they thinking? Jezzz


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