KEY WEST, Fla. — Sam Kaufman will take the mayor’s seat for the first time Thursday alongside new commissioners Mark Rossi and Chris Massicotte, and current commissioners Aaron Castillo, Lissette Carey, Vice Mayor Donie Lee, and Monica Haskel.
They will tackle the first agenda of a new dais, but much of the attention, however, may fall on someone who has been sitting at the commissions side for nearly a year: City Attorney Mayanne Downs.
Rossi placed a four-word discussion item on the Sept. 3 agenda: “City Attorney Contract Status.”
The backup consists of the resolution and engagement letter commissioners approved last October, when they hired Downs and her Orlando firm, Downs Aaron, as a temporary solution after a search failed to produce a permanent city attorney.
Downs is paid $495 an hour, plus expenses, under a month-to-month agreement that either side can end with 30 days’ notice. The deal was meant to last no more than 18 months, but the engagement letter set a goal of replacing her in less than a year.
That one-year mark arrives Oct. 13.
But her fate might be determined on Thursday
The 18-month limit falls in April. Rossi’s item doesn’t spell out what he wants the commission to do. There’s no proposed search, extension or termination on the agenda, and since October, Downs has billed $82,911.89 for reviewing emails, advising on legal issues, hiring other attorneys to defend the City in a multitude of law suits and travel back and forth from Orlando, where she and her firm also represent the City Beautiful and the Greater Orlando Airport Authority. She was originally hired by felony-indicted former City Attorney Ron Ramsingh to orchestrate the public execution of then City Manager Al Childress.
Kaufman opposed hiring Downs from the start — instead recommending Dirk Smits of Vernis & Bowling’s Islamorada office. The multi-state firm specializes in municpal law and had offered to do the job for half the price. In addition, they represent the Monroe County School District.
Downs future became a fixture on the campaign trail this year, with candidates asked at nearly every forum whether Key West should keep paying an outside Orlando attorney by the hour or restart its search for a permanent lawyer at City Hall.
The debate isn’t just about cost anymore.
Downs has had a sometimes-contentious relationship with commissioners, particularly over LGBTQ issues like rainbow-painted fence posts that appeared around Key West after the city removed rainbow crosswalks at Duval and Petronia streets.
Members of the Historic Architectural Review Commission tried to write a rule allowing homeowners to paint a limited number of fence pickets or a pedestrian gate on their property. Downs objected to how the proposal was being handled and raised legal concerns of her own. Kaufman complained in January that the city attorney’s office had failed to give clear, timely guidance, leaving residents and HARC members frustrated.
By May, the disagreement had become a federal lawsuit.
The ACLU of Florida sued Key West on behalf of Coley Sohn and Linda Bagley-Sohn, who had painted 12 pickets on their Old Town fence in rainbow colors. The couple repainted them white after the city threatened fines of up to $250 a day. Their suit accuses Key West of targeting the rainbow display over its message while ignoring other brightly painted fences, doors and shutters in the historic district; the city disputes the claim, and a judge has not ruled on it. Court records cited in the lawsuit trace the original code complaint to neighbor Penny Walker-Pourciau, who has posted anti-LGBTQ messages on social media. Downs is not named individually, but her office advises the city and oversees its defense.
But Wait… There’s More
City code officers sent violation notices to several property owners whose fences appeared in the federal complaint as examples of what the ACLU called selective enforcement — and the notices reportedly listed the Bagley-Sohns as the ones who complained. The couple said they never did; the photos were evidence in their own lawsuit, not tips for code enforcement. The ACLU has demanded the city correct the record, notify the affected owners and disclose who authorized the notices.
Critics have also pointed to Downs’ past appearance on a Federalist Society panel — a 2018 separation-of-powers discussion at the group’s Florida conference — when questioning her approach to legal issues in Key West.
While that association alone doesn’t show any opinion she’s given the city was politically motivated, but under the city charter, the call is the commission’s to make: the city attorney serves at its pleasure.
More Money for Waste Management via Change Orders
The morning meeting also brings two large requests from Waste Management Inc. of Florida, the only company that bid on the city’s sludge and solid-waste contracts last year. The company is coming back to City Hall hat in hand for another $640,000 combined.
One change order would add $190,000 to the sludge transportation and disposal purchase order. The other adds $450,000 for garbage, recycling and other solid-waste haul-out services. Neither contract guaranteed a total price — Waste Management bills by the ton, so the city’s cost rides on how much material gets hauled and where it ends up.
Still, the sludge numbers raise questions.
Waste Management charges $178.80 per wet ton. The city’s own solicitation estimated 6,000 wet tons a year, which pencils out to about $1.07 million, but Key West budgeted just $809,912 — enough for roughly 4,530 tons.
The proposed change order would bring the purchase order to $999,912, covering about 5,592 tons, still short of the 6,000-ton figure the city used when soliciting bids. In backup for the discussion, Utilities Director Matt Willman says the treatment plant simply generated more sludge than projected; the backup doesn’t explain why the budget landed below the solicitation estimate in the first place.
Staff says the contract has already saved the city about $145,737 by eliminating a 13% markup previously tacked onto Waste Management invoices. Even counting that savings, the purchase order still comes up 23.5% short.
The bigger change order covers solid-waste haul-out. Key West budgeted about $5.56 million and now says it needs another $450,000 to reach Sept. 30. Staff blames higher tonnage, the added cost of hauling recyclables and longer trips to more distant disposal sites, and says final contract rates weren’t available when the budget was drafted. But the item backup doesn’t include the invoices, tonnage reports, recycling totals or monthly projections that would let commissioners test any of it. Both increases sit on the consent agenda, where they can pass without discussion unless a commissioner pulls them.
Seeking Clarity on Water Testing
The contrast with another recent request is hard to ignore. In April, the previous commission rejected a $62,807.87 request to let Stantec Consulting Services resume water testing in Key West Harbor — less than a tenth of what Waste Management is asking for Thursday. That rejection helped put harbor monitoring on hold, and five months later, the consultant says testing still hinges on the city buying equipment.
The delay comes just as the commission receives a new report documenting repeated water-quality disturbances tied to cruise-ship traffic.
Researchers from the College of the Florida Keys and Florida International University tracked 301 cruise-ship visits between October 2023 and December 2024 and identified 35 turbidity events above the state criterion coinciding with ship arrivals or departures. The worst hit Aug. 20, 2024, when turbidity climbed to 200.11 nephelometric turbidity units — more than six times the state threshold cited in the report.
Hurricanes and tropical storms caused longer disturbances, but cruise ships were linked to shorter, more frequent spikes as propeller wash stirred sediment off the harbor bottom. Stantec says it has already gathered more than 395,000 data points from over 130 locations and prepared plans for beach and harbor testing, and now lists resuming harbor monitoring as the immediate priority — though its presentation doesn’t say when the equipment will actually be bought, or what it will cost.
Higgs Beach Plans Move Ahead Without Public Input
Higgs Beach is also back on the agenda as Key West settles into ownership of the 16.5-acre park it took over from Monroe County.
The city is already considering changes, including Astroturf for a dog park. That raises some basic questions in Key West: how hot the surface will get, how well it will drain and how it will hold up to dogs, waste and daily use.
Since taking over Higgs Beach, the city has held no public workshop or dedicated meeting to ask residents what they want at the park or what they think of the plans.
There is also the cost. The city estimates about $3.6 million for seawall and beach work and another $300,000 for sand renourishment, with other improvements still to come.
Monroe County sweetened the deal with financial incentives when Key West agreed to take the park. That money won’t last forever. Eventually, Key West will be responsible for the cost of operating, maintaining and improving Higgs Beach.
Mayor Kaufman has previously raised concerns about the long-term cost of the takeover.
The city wanted control of Higgs Beach. Well, now it has it. What it does with the park, what it costs and when the public gets a say are the next questions.
Happy Ending for Happy Landings?
Another long-running dispute returns Thursday at Happy Landings Marina, 2407 N. Roosevelt Blvd. City staff want the commission to declare the developed upland portion Commercial General while leaving the mangrove fringe and marina basin under conservation designations. The city labeled the property Conservation in a 2022 zoning-verification letter; the owner says commercial zoning was mistakenly dropped when city maps were updated.
There’s evidence of longstanding commercial activity on the site — a marine mammal attraction, restaurant, entertainment venue and offices — and a 2023 email in which a city planner concluded older maps had shown the upland portion as commercial.
The resolution calls the move an interpretation, not a rezoning. Attorney Barton Smith calls that a distinction without much difference, arguing the owner should have to seek formal zoning and Future Land Use Map amendments, with the public notice and review that come with them.
The 2023 staff email could hand him more ammunition: in recommending the interpretation route, the planner wrote that a formal amendment would cost more and be politically unpopular. Commissioners postponed the item in April, May and June, then withdrew it in July.
Also back on the table is a proposed 10-year, roughly $4.67 million agreement with Iron Brick Associates for the Workday financial and administrative system — down from an earlier figure near $5.32 million. Commissioners postponed it Aug. 6. The commission had asked staff to see if they could negotiate a better deal with the vendor, which apparently they did.
Rounding out the agenda: state transit grants, new planning and marina fees, Higgs Beach maintenance and cleanup, and Mallory Square projects, a possible rent reduction for El Meson de Pepe, and a public-art installation recognizing Key West’s LGBTQ+ history.
Public comment should be interesting, with speakers expected to express concerns about the City and KWPD’s use of Artificial Intelligence and the 44-page whistleblower complaint levied by KWPD officer Dustin Christina.
The morning session begins at 9 a.m. at City Hall, 1300 White St. The commission returns at 5 p.m. for the water-quality presentation and evening agenda. For those unable to attend, the meeting will be streamed live on the city’s website.
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