A Humble Editorial, In Which We Try, And Fail, To Understand How A Town Of 7,500 People Has Spent Approximately The Gross Domestic Product Of A Small Caribbean Nation Arguing About A Sign.
—I would like to begin by saying that I love Longboat Key. I love its dolphins, its sea oats, its astonishingly well-organized recycling pickup, and the way the entire island achieves an unspoken collective consensus, around 9:47 p.m. every evening, that it is now bedtime.
—But I am here to report, with great sadness and only mild caffeination, that we have lost our minds. We have, as a community, become so deeply invested in the question of whether a fourteen-foot piece of welded marine-grade stainless steel may exist on a concrete groin sticking into the Gulf of America (formerly Mexico, formerly Mexico, currently Mexico, depending on who is reading your map) that future archaeologists are going to dig us up and assume we worshipped it.
—A Brief, Helpful Timeline For Newcomers
—In August of 2025, the St. Regis built an arch. The arch was beautiful. The arch was also unpermitted. This is the equivalent of showing up to a wedding wearing a tuxedo you sewed yourself out of curtains: people may admire the workmanship, but they will also wonder why you did not, at any point, consult the bride.
—The Town said: take it down.
—The St. Regis said: but it’s so pretty.
The Town said: we have a Code.
—The St. Regis said: but Instagram.
—And thus began The Year Of The Arch, an extended period of municipal anguish during which approximately every adult on this island has been asked to develop, defend, and possibly tattoo onto their forearm a personal position on signage policy.
—The Draping Of The Sign, Or, We Have Become A Nation Of Faux-Greenery People
—For most of the past year, the offending sign portion of the arch was covered in faux greenery, which is a phrase I never expected to type, much less type repeatedly. I will say, in defense of faux greenery, that it represents a noble Floridian compromise: when in doubt, cover the problem with something that looks like a plant.
—Then, last Friday at 5:00 p.m. — a deadline set by Town Manager Howard Tipton, who I imagine has not slept since approximately Labor Day — the developer removed the faux greenery. The Town’s lawsuit, which I have read in its entirety because apparently this is my life now, describes this as “doubling down.” It is the only time in recorded legal history that the phrase “doubled down” has been deployed in reference to fabric foliage, and I would like that fact to be entered into the Congressional Record.
—Things The Town Has Now Produced In Connection With This Arch
—A constitutional memorandum. Two ordinances. A draft Text Amendment. A second draft Text Amendment. A withdrawal of both draft Text Amendments. Two Planning and Zoning Board denials. One Town Commission resolution. One special counsel engagement letter. One 5:00 p.m. deadline. One phone call. And, as of Thursday afternoon at 2:19 p.m., one thirteen-page Complaint for Mandatory Injunctive Relief, plus three exhibits, plus several attached aerial photographs in which our beautiful island looks, from space, like a thin and indignant fish.
—Things The Developer Has Now Produced In Connection With This Arch
—The arch.
—The Quotes Era
—In recent weeks, we have entered what historians will surely call The Quotes Era. Chuck Whittall, the developer, has compared the arch to “a 1950s Monaco pier,” which is a wonderful image except for the part where Monaco is not actually known for piers, but rather for casinos, royalty, and Formula One drivers behaving badly on yachts. He has called the arch “an Instagram memory moment,” which I am told is a thing, and “a true landmark,” which it is rapidly becoming, though not in the way he intended. He has also informed us he will fight this case to the Florida Supreme Court, which is the legal equivalent of telling your spouse you will die on this hill, except that you have rented the hill, the hill is on state submerged land, and the hill is currently in litigation.
—Town Attorney Maggie Mooney, by contrast, has produced sentences containing phrases like “content-neutral regulation” and “Section 158.094(C),” and I would just like to take a moment to thank her, because somebody has to be the grownup, and apparently it is going to be a woman with footnote citations.
—What This Is Really About
—It is not, of course, about the arch.
—It is about whether a town gets to enforce its rules against a developer who has spent $600 million, employs more attorneys than several Caribbean nations have citizens, and possesses an absolutely magnificent ability to call things landmarks until they become landmarks.
—It is also about whether the rest of us — the people who actually went down to Town Hall and got a permit to build a pergola — feel like chumps. (For the record: yes. We feel like chumps.)
—A Modest Proposal
—I propose the Town and the developer settle this immediately, as follows: the arch stays, but every wedding photo taken beneath it must include, in the corner, in small print, the text “PHOTOGRAPHED IN VIOLATION OF SECTIONS 158.094(C), 158.099(A), 156.05, AND 156.07 OF THE TOWN OF LONGBOAT KEY CODE OF ORDINANCES, IRREPARABLE HARM IS PRESUMED, SEE WARE V. POLK COUNTY, 918 SO. 2D 977.”
—You’re welcome. I’ll be at the beach.
—The opinions expressed in this editorial are those of the editorial writer and not necessarily those of his attorney or his psychologist.
