DEEP DIVE: Key West Commission Confronts Competing Mallory Square Proposals
Cable Huts, historic leases raise questions about access, control and process - as well as the Bubba system being alive and well.
KEY WEST, Fla. — The Key West City Commission is expected to vote Wednesday on a slate of redevelopment agreements that would reshape Mallory Square, awarding multiple historic leaseholds to Tropical Shell & Gift, Inc. — and by extension its parent company, Historic Tours of America — amid objections from a competing bidder who says the process and outcome deserve closer public scrutiny.
At issue are three proposed lease awards covering the Historic Hospitality House, 402 Wall St., and the Cable Huts at Mallory Square, a move that would consolidate control of several high-profile city-owned properties under a single operator tied to the Key West Aquarium.
The Hospitality House was built after the Great Fire in 1886 and was originally used as a ticket office for passenger and freight service by Tift and Company. In the 1960s, the building was relocated from its original site and restored. It was then used as the headquarters for the Old Island Restoration Foundation and as a hospitality center for welcoming visitors to Key West.
These Cable Huts are octagonal concrete structures built to store cable, used for communications between Key West, the West Indies and South America. The first cable connecting Key West with Cuba and Florida’s mainland was begun to be laid in 1867. The Eastern cable hut was constructed in 1921, while the Western hut was constructed later in 1932.
The structures have fallen into a state of disrepair for decades.
City procurement officials have recommended awarding the contracts to Tropical Shell following a re-bid process in which the company received the highest overall evaluation score.
Under the proposed agreements, Tropical Shell would assume full responsibility for design, permitting, rehabilitation, operation and maintenance of the properties, with no direct financial impact to the city.
The company’s proposal centers on expanding the footprint and mission of the for-profit Key West Aquarium, converting the Historic Hospitality House into an environmental education and conservation hub with interactive exhibits, classroom space and nonprofit partnerships.
The plan emphasizes integration with the aquarium’s existing operations, with programming and access tied to general admission, and revenues from ticketing used to fund maintenance, staffing and city lease obligations.
That model effectively shifts portions of the space toward a structured, ticketed experience connected to aquarium programming.
By contrast, a competing proposal from Hayes Robertson Group — led by developer and restaurateur Joe Walsh — places greater emphasis on maintaining open public access and activating Mallory Square through food, beverage and public-facing uses.
Hayes Robertson Group is tied to a portfolio of locally known restaurant operations associated with Walsh, including Caroline’s Cafe, the Waterfront Brewery and Jack Flats, all of which emphasize high-volume service and integration with Key West’s tourism-driven pedestrian corridors.
Walsh has positioned the group’s proposal around preserving the square’s traditional, open-access character while enhancing it with curated food and beverage offerings designed to activate the space throughout the day and evening.
His concept allowing visitors and residents to circulate freely without requiring admission, while reinforcing Mallory Square’s identity as a civic gathering space tied to its historic sunset marketplace.
Walsh urged commissioners to allow both proposals to be publicly presented before taking action, arguing that the evaluation process relied heavily on subjective criteria.
“The redevelopment of Mallory Square is worth the time and effort,” Walsh wrote in an email on March 16 to city procurement officials.
However, Walsh emailed the Mayor and Commissioners directly on March 29, again saying his firm scored higher in “vision for Mallory Square” across reviewers and questioned aspects of the scoring related to financial capacity and evaluator familiarity with the Mallory Square Master Plan.
He did not contest the recommended award for the 402 Wall St. property, but said the Hospitality House and Cable Huts — located at the center of the city’s waterfront — should be fully vetted given their long-term impact on public access and use.
City procurement records show the recommendation follows a re-bid process after an earlier solicitation yielded only one responsive proposal, limiting competition. The revised solicitation produced two proposals, with Tropical Shell ranked highest by the evaluation committee.
Beyond the proposals themselves, the vote is unfolding against a backdrop of local campaign finance scrutiny.
Another question surrounding the decision is the extent to which Tropical Shell & Gift and its parent company, Historic Tours of America, have financially supported candidates currently sitting on the dais during the 2026 election cycle.
Althought the first quarter results for 2026 campaign finance records arent due for another 10 days, records from the 2024 race show that several commissioners — mainly Mayor Danise Henriquez, Vice Mayor Donie Lee and Commissioner Aaron Castillo — received the maximum $1,000 contributions either from the entities or executives associated with the tourism conglomerate.
The overlap between campaign contributions and a pending vote involving a major city contract has raised broader questions about influence, transparency and public trust, even as no allegations of wrongdoing have been formally made in connection with the agenda items.
If approved, the agreements would mark a significant shift in how Mallory Square’s historic assets are managed, consolidating multiple properties under a single operator aligned with a tourism and attractions-based model.
It would also likely be the last piece of the puzzle in city-owned properties leased and managed by Swift-affiliated companies.
The decision places commissioners at the center of a broader policy question: whether the future of Mallory Square is best served by a coordinated, program-driven model tied to ticketed attractions, or by a more open, publicly accessible approach anchored by food, beverage and traditional street-level activity.
Lease items for Mallory Square are expected to be heard during the morning session beginning at 9 a.m. at 1300 White Street, and an afternoon session is scheduled for 5 p.m. Both will be streamed live on the City’s website.
Tags: Key West, Mallory Square, City Commission, Cable Huts, Tropical Shell, Historic Tours of America, Hayes Robertson Group, Joe Walsh, campaign finance, development, public access