a large white building with palm trees in front of it
The Key West City Commission meets today, June 26, to consider a motion to fire city manager Al Childress. MANDY MILES/Keys Weekly

Three Key West lawmakers who are leaving office in a few months want to fire the city manager on their way out the door. But the man they hoped would replace the city’s top official just resigned on Monday, June 17, effective immediately.

The commission is scheduled to vote on terminating City Manager Al Childress’ contract during a special meeting at 2 p.m on Wednesday, June 26 at city hall. Commissioners Lissette Carey, Jimmy Weekley, Clayton Lopez and Billy Wardlow are allegedly the four votes it would take to oust Childress.

But let’s back up a few days. How did we get here?

Childress, who started the city manager job in April 2023 with a four-year contract, got a call the evening of June 14 from city attorney Ron Ramsingh.

“He called to tell me there are four votes from commissioners to fire me; that they’re planning to call a special meeting to do it,” Childress told the Keys Weekly shortly after the conversation and still reeling from the news. He named Weekley, Lopez, Wardlow and Carey as the four votes to oust him.

a close up of a person wearing a suit and tie
The Key West city commission will vote June 26 whether to fire city manager Al Childress, who started the job in April 2023. CONTRIBUTED

Weekley, Lopez and Wardlow are term-limited out of office after the upcoming election, and Mayor Teri Johnston, who supports Childress, chose not to run again, meaning four of the seven city lawmakers will be brand new in November — and possibly in need of a new city manager. 

Commissioners Carey, Sam Kaufman and Mary Lou Hoover will remain on the dais. They’ll be  joined after the Aug. 20  primary by incoming Mayor DeeDee Henriquez, new Commissioner Donie Lee, who replaces Wardlow, and the winner of the District 1 race for Weekley’s seat — either Monica Haskell or Ben Hennington. Lopez’s successor in District 6 will be determined in the November general election unless one of the three candidates — Aaron Castillo, Thaddeus Cohen and Marci Rose — earns more than 50% of the vote in the August primary.

The June 14 news of Childress’ opposition came two days after assistant city manager Todd Stoughton tendered his resignation, initially writing that he’d leave his last day “open-ended to allow enough time for a replacement to be named.”

“The hope would be that Todd would step in as interim city manager so we have some stability for the new mayor and commissioners,” Carey said the night of June 14, acknowledging that she will vote to fire Childress.

But just a few days later, on Monday, June 17, Stoughton made his resignation effective immediately, telling the Keys Weekly that the decision to leave was entirely his own, but declining to comment further.

Weekley told the Keys Weekly the next day he didn’t believe it.

“I’m hearing the mayor and Commissioner Kaufman pressured him to leave,” Weekley said on June 18. “So I would hope we could bring Todd back on an interim basis. If Todd declines, then perhaps the city attorney could step in until the new commission finds a replacement.”

When asked whether the decision to fire the city’s top official is one that should be left to the new commission, Weekley said, “It’s better to get this resolved now. I hate seeing it happen like this, but this is something that has to be done, and right now, the incoming commission is still on the outside looking in.”

Weekley said he’s heard of morale problems among city employees, “who have told me things in confidence that have led to my decision.”

Carey frequently has been critical of Childress at commission meetings and in her evaluation of him in April, writing, “The city manager needs to work on a better understanding of the needs of the Keys community and the will of the residents. While his previous experience in Miami provides him with relevant experience in municipal government, the initiatives he is attempting to duplicate in Key West are out of touch with what our citizens want.”

Johnston, on the other hand, wrote of Childress in April, “I have worked with six city managers, and Al Childress is the most qualified, transparent, equitable, efficient and principled city manager I have had the pleasure of working with.” 

Johnston again commended Childress over the past week when speaking with the Keys Weekly. Hoover lamented Stoughton’s resignation and commended his work, while echoing the mayor’s support for Childress and the turmoil his ouster would cause for the new leaders.

If the vote to fire Childress occurs on June 26, it will cost the city about $100,000. His contract provides for 20 weeks of pay if the commissioners end his contract early. With an annual salary of $225,000, five months of pay equals $93,000.

Mandy Miles
Mandy Miles drops stuff, breaks things and falls down more than any adult should. An award-winning writer, reporter and columnist, she's been stringing words together in Key West since 1998. "Local news is crucial," she says. "It informs and connects a community. It prompts conversation. It gets people involved, holds people accountable. The Keys Weekly takes its responsibility seriously. Our owners are raising families in Key West & Marathon. Our writers live in the communities we cover - Key West, Marathon & the Upper Keys. We respect our readers. We question our leaders. We believe in the Florida Keys community. And we like to have a good time." Mandy's married to a saintly — and handy — fishing captain, and can't imagine living anywhere else.