It’s been a hell of a year. From corruption and crosswalks to ICE raids and commission campaigns. Happy New Year, Key West. Here’s to perhaps a smoother 2026.
JANUARY
- Brian L. Barroso begins work as Key West city manager with a $215K starting salary that increased to $230K after a six-month probationary period. The contract will automatically renew in 2027 for another two years unless Barroso or the city commission wants to change or end it.
- Sherri Hodies is sworn in as Monroe County Supervisor of Elections following some upheaval within the Monroe County Republican Party.
- The Wounded Warrior Project returns to Key West for the 20th year of its Soldier Ride.
- The Key West Literary Seminar welcomes author John Irving and dozens of other internationally acclaimed writers for four days of readings, panel discussions and receptions.
- Key West firefighter and real estate agent Austin Kimbler was arrested for possession of anabolic steroids, cocaine and a designer drug known as “Tussi,” which is a mix of cocaine, methamphetamine and ketamine.
- Concerned residents formalize efforts to urge hospital district board members to seek proposals from multiple health care companies interested in running Lower Keys Medical Center, Key West’s only public hospital, before the current company’s 30-year lease ends in 2029.
- President Donald Trump taps Key West businessman and environmental consultant Ed Russo to chair Trump’s environmental advisory task force, “which will advise my Administration on initiatives to create great jobs and protect our natural resources, by following my policy of CLEAN AIR and CLEAN WATER. Together, we will achieve American Energy DOMINANCE, rebuild our Economy, and DRILL, BABY, DRILL,” Trump posted on Truth Social when announcing the appointment.
- Jenny Lorenz is named CEO of Overseas Media Group, the Keys Weekly’s sister company that specializes in digital and social media marketing.
- The Monroe County School Board launches a national search for the next superintendent.
- Florida Keys charter boat Capt. Laurence Lewis is arrested by state wildlife officers for allegedly operating a vessel under the influence at the time of a July 2024 crash that injured seven people in the Lower Keys. The Florida Fish & Wildlife Conservation Commission’s investigation showed Lee was operating the 35-foot vessel when it hit the South Pine Channel Bridge at high speed, throwing multiple passengers overboard.
- A Jan. 23 fire in public housing apartments on Emma Street devastates a local family, killing two parents and one child, 5. Three other children were severely injured and taken to mainland hospitals, where a 7-year-old succumbed to his injuries on Jan. 25, bringing the death toll to four.
- Community activist Shirlee Ezmirly dies at the age of 97, having lived in Key West since 1981, when working for the U.S. Coast Guard as a civilian. She was known for her daily walks around town and for her role with the Key West Rip-Off Rapid Response Team that relentlessly picketed predatory cosmetic shops on Duval Street.
- A Marathon man who was sentenced to 45 months in prison for his role in the Jan. 6, 2021 Capitol riots in Washington, D.C. was set free after serving fewer than five months when Trump pardoned more than 1,000 convicted rioters.
- A Key West man is arrested with 40 grams — 20,000 lethal doses — of fentanyl after multiple overdoses had occurred in the city. Key West police detectives traced the source to a man living across the street from Key West High School. William Edward Madalinski, 51, was arrested. Authorities also seized 77 grams of cocaine, 25 grams of MDMA and 3.2 grams of ecstasy pills.
- The basketball court at Horace O’Bryant School is renamed in memory of Coach Dexter Butler, who died in March 2024 at the age of 37.
FEBRUARY
- City Commissioner Donie Lee proposes a partnership in which the Navy would lease the city 18 acres of land at Sigsbee Park, so the city could rebuild more than 166 housing units that the Navy has failed to replace after demolishing the townhomes in 2021. The units were flooded in Hurricane Wilma in 2005, then sat empty for 16 years aside from the mold that made the units unlivable.
- An advisory committee of concerned residents persuade a majority of hospital district board members to hire an independent legal representative to help the committee solicit proposals for a new hospital operator.
- ICE anxiety grips Keys immigrants as advocates and officials brace for effects of Trump’s mass deportation campaign to remove undocumented immigrants from the country. This was only the beginning of policies and practices that would upend the lives of local immigrants, including those with pending asylum cases who had been granted work authorizations.
- The Key West Aquarium, the island’s first tourism attraction that emerged from the Great Depression, celebrates its 90th anniversary.
- The Key West Weekly welcomes columnist Carol Shaughnessy to our pages. Her “Key West Back in the Day” columns revisit the Key West we all wish we had experienced in the 1970s and ’80s. She alternates those features with twice-monthly profiles of “People You Should Know.”
- Judge Mark Jones denies Preston Brewer’s self-defense claim in shooting death of Garrett Hughes.
- Military officials survey Sigsbee Park residents about mold and other housing concerns.
- Rams Head Presents brings country music legend Willie Nelson back to Key West to perform at the Coffee Butler Amphitheater at the age of 92.
- Brittany Holbrook is convicted of second-degree murder for the fatal June 2023 shooting of her then-boyfriend Tyler Nulisch on Big Coppitt Key.
MARCH
- Federal turmoil affects Florida Keys; tariffs and Canadian travel boycotts could affect tourism and threaten jobs.
- Rams Head brings the Beach Boys and their good vibrations to the Coffee Butler Amphitheater.
- Hospital board hears preliminary proposals from companies interested in running Lower Keys Medical Center when the current long-term lease with Community Health Systems ends in 2029.
- Gov. Ron DeSantis vetoes all components of the Florida Keys National Marine Sanctuary’s newly-finalized Restoration Blueprint in state waters.
- ‘Cops’ TV show features spring break in Key West on March 7 episode.
- Judge allows Brewer a $3 million bond to remain on house arrest while awaiting trial for the shooting death of Garrett Hughes. (As of Dec. 11, Brewer had not posted the bond and remained in the Monroe County Detention Center on Stock Island.)
- Key West officials and residents celebrate the opening of the long-awaited new Frederick Douglass Community Center in Bahama Village.
- Local panelists look back on the COVID pandemic, on the fifth anniversary of the March 2020 shutdown that changed our world.
- Breeze Airways announces that it will begin offering flights to and from Tampa and Orlando starting in June 2025.
- Former Key West firefighter Vincent M. Vega is arrested following a traffic stop, when he was reportedly traveling 69 mph in a 30 mph zone. In his car, police found a loaded AR-15 that had been illegally modified to shorten the barrel. A subsequent search warrant for Vega’s bedroom revealed 20 guns, 10,000 rounds of ammunition, bomb-making materials and a diagram of a Key West building. (Update: Vega’s case has been moved to federal court. He agreed to plead guilty to possession of an illegal firearm and possession of an explosive device. He is scheduled to be sentenced on Jan. 21 in a Miami federal court.)
- Catholic Charities opens 10 new affordable apartments for people living with disabilities at St. Bede’s Village on Flagler Avenue.
- Lower Keys Medical Center announces that Drew Bigby, former CEO of Walter Reed military hospital, will take over as CEO of LKMC on April 28.
- Federal funding cuts prompt summer camp cancellations at Dry Tortugas National Park and peaceful protests along Truman Avenue.
- Key West raises a glass at Truman Waterfront for the 30th Taste of Key West fundraiser.
- The Blue Angels return to the skies over Key West for the Southernmost Air Spectacular.
APRIL
- City commissioners back homeowners and deny the Casa Marina Hotel’s rezoning request that would have enabled it to create 20 or so new hotel rooms.
- Publix announces plans to build a new Searstown Plaza — but no affordable housing to go with it.
- The Key West Wildlife Center, which rescues and treats injured birds, opened its new avian clinic at Indigenous Park.
- Square Grouper Key West opens to rave reviews on Caroline Street.
- More than 600 protesters join Key West’s Hands Off protests in opposition to federal funding cuts.
- The Monroe County school district continues its search for a new superintendent; narrows list from 32 to 11 candidates.
- Military families, including some in Key West, sue military housing provider Balfour Beatty, citing ‘horrific conditions’ in base housing.
- Scandal erupts within Key West’s city hall with the arrest & indictment of officials Raj Ramsingh, Ron Ramsingh and Jim Young.
- The new terminal at Key West International Airport welcomes first passengers.
- Brittany Holbrook of Big Coppitt Key is sentenced to 40 years in prison for the 2023 killing of her boyfriend, Tyler Nulisch.
- Plot thickens with city hall corruption probe; subpoenaed texts reveal plot to oust former city manager.
- Key West city attorney Ron Ramsingh is on his way out amid an indictment & corruption probe.
MAY
- County school board members hire Ed Tierney as superintendent after a comprehensive search and interview process.
- Nashville artists fill the island for the annual Key West Songwriters’ Festival.
- Key West city attorney is terminated without cause, meaning he walks with a $220,000 payout following multiple indictments.
- More charges filed against the brothers Ramsingh amid city hall corruption investigation.
- A near-fatal shooting starts with a fight over macaroni and cheese on Greene Street. Alijah Helmar of Key West is arrested.
- Harry Russell announces campaign for the Key West City Commission, District 5.
- FBI interviews of current & former city employees detail favors & cronyism at city hall.
- DeSantis & Florida Keys Aqueduct Authority dedicate a new water desalination plant on Stock Island, named for former Key West Mayor Kermit Lewin.
- Patrick Wright returns to Key West city hall as newly appointed growth management director.
- City Manager Brian L. Barroso suspends former Key West chief building official Raj Ramsingh without pay, ending three weeks of paid administrative leave while city officials investigate allegations against him.
- Class of 2025 graduates Key West High School, accepting diplomas at the newly renovated Tommy Roberts Memorial Stadium.
- George Fernandez donates $1 million to Baptist Health to honor the late Michael Halpern and keep cancer treatment available in Key West.
- Miss Island Queen amateur drag pageant raises $180K for nonprofit women’s shelter.
- Florida’s decision to ban fluoride from drinking water concerns Key West dentists.
- Somerset Island Prep charter high school continues tradition with sixth-annual jet ski graduation.
JUNE
- Grand jury report reveals ‘network of fraud & criminal acts’ inside Key West’s city government.
- Proposed marina rent hikes threaten to sink Key West’s houseboat community — then commissioners approve protections.
- CFK Academy, a new charter high school on the College of the Florida Keys campus, graduates its first class.
- Despite federal staffing cuts, Keys weather experts at NOAA forecast office are ready for storm season.
- Capt. Colin Thompson takes helm as commander of Naval Air Station Key West from Capt. Beth Regoli.
- Key West voters in District 4 start researching the legal process to initiate a recall election to remove commissioner Lissette Carey from office in the wake of the continuing corruption probe. (Carey has not been charged.)
- School board members approve a three-year contract for new superintendent Ed Tierney.
- Florida Keys face immigration anxiety amid ICE raids.
- Key West residents pack Bayview Park for nationwide No Kings protest.
- Online voting begins to choose the 2025 winners of The Bubbas: Key West People’s Choice Awards.
- Key West is drenched in color — and Pride.
- Popular Key West hairstylist Lee Stinton detained by ICE and later sent back to Ireland.
- Volunteers rescue 19 baby sea turtles from storm drain on S. Roosevelt Boulevard.
- Capt. Josh Empen takes helm of Coast Guard Sector Key West from Capt. Jason Ingram.
JULY
- Key West officials void the city’s cooperative agreement between Key West police and ICE.
- Longtime teacher, principal and superintendent Theresa Axford retires after more than 30 years.
- City commission meeting goes off the rails amid corruption probe, as indignant residents booed five of seven local lawmakers who voted to make them wait more than three hours to offer public comment.
- Key West officials reverse course and approve a cooperate 287(g) agreement with ICE despite public uproar.
- Monroe County school district earns an A grade.
- Ed Tierney takes reins as new superintendent of schools.
- ICE detains, then deports, Key West landscaper who had a work visa & pending asylum case and no criminal record.
- Key West Bubba Awards welcomes votes from all 50 states and six of seven continents.
- Recall effort to remove Carey from office finds volunteers collecting petition signatures.
- Key West rallies for its rainbow crosswalks after the state deems them unsafe.
- Appeals court denies Brewer’s self-defense appeal, allowing trial preparation to proceed.
AUGUST
- Carey sues to stop recall efforts against her, after saying she’d let the democratic process play out.
- Tempers flare in testy city budget talks as officials consider 4% to 7% tax increase.
- State law requires Hodies to reject recall petitions against Carey. Signatures were not collected within the required timeframe.
- Key West still needs a permanent city attorney.
- CW Colt’s “We Are One Human Family” becomes Key West’s official song.
- Sunshine State won’t tolerate crosswalks. FDOT bans, then removes, Key West’s rainbow crosswalks.
- College of the Florida Keys turns 60.
- ICE agent arrested for DUI with his kids in the car — and heading the wrong direction.
- College of the Florida Keys reopens ceramics program.
- Ethics complaints dismissed against Key West commissioners Monica Haskell and Sam Kaufman.
- Keys resident Tyler Howell Nolan sentenced to 18 months in prison for revenge porn.
- Key West seeks new rainbow ideas in preparation for state-mandated crosswalk removal.
- Key West businessman Peter E. Batty sues county tax collector Sam Steele — over kids baseball.
SEPTEMBER
- Just a Few Friends Festival honors Jimmy Buffett with music and margaritas over Labor Day weekend.
- Key West Housing Authority announces end of assisted-living units at Poinciana Gardens.
- State officially erases Key West’s rainbow crosswalks.
- Southernmost Point buoy moves temporarily to Duval Pocket Park.
- Truman Annex property owners prepare to lose their short-term rentals rights in December.
- Monroe County Sheriff’s Office Capt. Jonathan Crane completes FBI training academy.
- Key West’s former building official Raj Ramsingh picks up 7 new charges amid ongoing Key West corruption scandal.
- Is Florida now the Gunshine State? Court ruling allows open-carry of firearms.
- Navy housing company Balfour Beatty faces 80 more accusers in lawsuit over poor quality military housing.
- The Navy’s objection threatens a new mooring field near Wisteria Island.
- Jail deputies arrested for allegedly conspiring to smuggle fentanyl into the Stock Island jail.
OCTOBER
- Key West plans a permanent Pride display to replace painted crosswalks.
- Key West Fire Departments turns 150
- Rhonda Lopez and Hodies cleared in election fraud complaint.
- Indicted former county administrator Roman Gastesi gets one year — or less — of probation; no jail time.
- Key West wonders how a federal shutdown could affect the island.
- Female impersonator Mulan Alexander is chosen to ride the iconic high-heeled shoe on New Year’s Eve at Bourbon Street Pub.
- Costumed chaos delights during another Fantasy Fest.
- Community members continue to seek a new operator for Lower Keys Medical Center.
- Tourist Development Council launches new website at visitfloridakeys.com.
- City Commissioner Sam Kaufman enters the mayor’s race.
- Sarah Compton files to run for Carey’s seat.
- Chris Massicotte joins District 5 commission race against Harry Russell.
- Tats for Tatas raises $491K for women’s health and breast cancer screenings.
NOVEMBER
- Keys Weekly joins a humanitarian flight to Montego Bay, Jamaica following a devastating hurricane.
- Long-awaited Lofts, affordable housing units, opens at Truman Waterfront.
- Hodies improves website and joins social media.
- Local food pantries fill a bigger need than usual amid government shutdown.
- Mark Rossi and Bobi Lore to run for city commission, District 2.
- City Commissioner Mary Lou Hoover passes away.
- Actors Steve Buscemi & Aiden Quinn visit Key West Film Festival to honor Sir Billy Connolly.
- City officials to consider future of Jimmy Buffett’s old recording studio.
- Juan Llera enters city commission race in District 4.
- Former deputy Jennifer Ketcham sentenced to three years in prison after giving her then-boyfriend information about narcotics operations.
DECEMBER
- Key West commissioners appoint former city manager Greg Veliz to finish the term of Hoover.
- Southernmost City shines with holiday sparkle.
- State investigates Key West Cemetery after exposed human bones were discovered.
- Florida Keys immigrants continue to face ICE raids and detention.
- Time’s up for transient rental in Truman Annex neighborhood; 20-year legal settlement ends Dec. 22.
