The swearing-in ceremony at noon on Monday, Aug. 26 marks a significant change in the lineup of Key West politics, as incoming Mayor Danise “Dee Dee” Henriquez takes the field for the home team with two new players on the roster. She’ll join incoming city commissioners Donie Lee and Monica Haskell as they take the oath of office. They’ll join remaining commissioners Lissette Cuervo-Carey, Mary Lou Hoover, Sam Kaufman and Clayton Lopez. Lopez, however, will leave office in November, when a runoff election between Aaron Castillo and Marci Rose determines his successor.
A city commission meeting previously scheduled for 5 p.m. Monday, to decide whether the commission would rehire city manager Al Childress, was canceled days prior to the meeting, leaving the role of city manager still in limbo with Todd Stoughton happy to fill the role in the interim.
Already ubiquitous in politics, baseball metaphors are particularly difficult to avoid in Key West, where the incoming mayor has been married for 43 years to Key West High School’s winningest coach, Ralph Henriquez.
But make no mistake, when Dee Dee Henriquez takes the oath of office on Monday, she’s the one calling the shots.
“Everyone knows how I am with taxpayer money, and I didn’t come here to dust the shelves” that are filled with three-ring binders containing studies, reports and consultants’ long-term plans, Henriquez said on Friday, Aug. 23, when she sat down with the Keys Weekly in the mayor’s conference room at city hall while her new office was being repainted. “I want the citizens to see that we’re moving forward. Immediately.”
Having spent 31 years in the Monroe County Tax Collector’s office — 20 of them as the elected tax collector — Henriquez has a sharp eye for public money, property taxes and illegal vacation rentals, which her office was tasked with enforcing. She retired from that office in 2019 and spent all of 18 months as a retiree. She and Coach Ralph also own the Kilwins franchise on Duval Street, selling gourmet chocolates, fudge, ice cream and other treats.
“Then I spoke with County Clerk Kevin Madok, and went to work for him on special projects, record retention, sort of a director of operations, and we’ve come a long way in that office.”
When Henriquez told Madok in October 2023 she had decided to run for mayor, “he wasn’t ready to let me go, but instead said, ‘We’ll figure out a new schedule for you,’” Henriquez said.
She’ll still put in a few hours a day at the clerk’s office, but emphasized that the job of mayor is her top priority.
“I’ll always be here, whenever and for whomever I’m needed,” she said, adding that her office door will always be open — to city employees, department heads and residents.
Henriquez spent last week in city hall going through an orientation process, but her involvement in day-to-day city operations started nearly a year ago, when she announced her candidacy.
“I hit the ground running when I announced in October,” she said, assuming that she’d have an opponent, either in then-incumbent mayor Teri Johnston, who had one term remaining, or Kaufman, who had considered a mayoral run last fall. “I rode with the police officers on the night shift. I did shifts with the firefighters and in the ambulance. I went to every budget meeting, every commission meeting. I was out on the street at 4 a.m. while crews were cleaning up after Fantasy Fest. I ran as if I was running against 10 Teri Johnstons and 10 Sam Kaufmans.”
But in January, Johnston announced she wouldn’t seek reelection, and Kaufman decided to keep his commission seat. By June, when the qualifying period ended and closed the window for anyone to enter the race, Henriquez was unofficially elected without any opposition.
“I was so humbled by that,” she said. “It was encouraging to realize that people had trust in me, and in my commitment to trust, communication and transparency. I may be firm, but I’ll always listen and I’ll always be fair, and people will always know where things stand with me.”
That much was evident during Friday’s conversation, when Henriquez didn’t hesitate to make her position known about a few key issues.
She has already met with the city’s finance department to start the ball moving to enable the acceptance of online payments for businesses’ annual renewal of their business licenses, a feature not currently possible.
While many politicians speak around a question, pledging to “consider all sides, meet with the voters and make a decision later, Henriquez has already said, on the record, that she does not support extending the transient rental rights of property owners in Truman Annex.
She has already met with those owners, who were given a 20-year allowance to rent their places short term. That allowance ends in 2025, and there is already movement on the part of some property owners to seek an extension.
“I’ve met with (Code Compliance Director) Jim Young about vacation rentals, and I met with the Truman Annex property owners, and told them I would not support an extension.”
Henriquez also told the Keys Weekly that she does not support the rehiring of Childress, but acknowledges that the decision could come down to a vote of the entire commission if proposed by another lawmaker.
“Right now, city hall is divided,” she said. “People don’t know who to talk to, who to trust, who’s going to hear what. And so, whether it’s right or wrong, I can’t support bringing Mr. Childress back. I told Commissioner Kaufman that when we could still speak before the Sunshine Law took effect.” (Florida’s Government in the Sunshine law prohibits elected officials from privately discussing matters that could come before them for a vote.)
“I’m going to represent everyone and make my decisions on what’s best for everyone,” said Henriquez. “And people will always know where I stand.”
Oh, and on Monday evening, Aug. 26, she’ll be standing with her family — husband Ralph and their two adult children, Ralphie and Ashley, at Tavern ‘n’ Town, for a celebration that is open to the public at 5:30 p.m.
