Formerly: Sloppy Joe's (1933–1937; exact move year disputed)
Key West, Florida · Founded 1958 · Building: circa 1851–1852
A 1958 Key West saloon at the former 1930s Sloppy Joe's location, with Hemingway lore, Jimmy Buffett history, and a modern Mike Leach connection.
Captain Tony's Saloon opened under that name in 1958, when charter-boat captain Anthony “Tony” Tarracino took over the bar at 428 Greene Street. The address had previously housed Joe Russell's 1930s Sloppy Joe's, which later moved to Duval Street. Its famous tree, older-building stories, and celebrity associations make the place a Key West landmark, but the record supports some of those stories much more firmly than others.
Sources variously date the building at 428 Greene Street to 1851 or 1852. No primary construction record was located in this research.
Source: Captain Tony's Saloon history page; Old Town Manor, “Legends of Captain Tony's Saloon”
Joe “Josie” Russell began operating a bar at 428 Greene Street on the day Prohibition was repealed; later reporting identifies it as the earlier location of Sloppy Joe's.
Source: Sun Sentinel, “2 Key West bars battle for claim to be Hemingway's original Sloppy Joe's,” July 21, 2004
Ernest Hemingway was reported to have spent evenings at Russell's Greene Street bar between 1933 and 1937.
Source: Sun Sentinel, “2 Key West bars battle for claim to be Hemingway's original Sloppy Joe's,” July 21, 2004
The Sun Sentinel reported that Russell moved Sloppy Joe's from Greene Street to 201 Duval Street in 1937. Captain Tony's own history gives 1938, so the precise year remains disputed.
Source: Sun Sentinel, July 21, 2004; Captain Tony's Saloon history page
Secondary histories report that Captain Tony Tarracino purchased the bar at 428 Greene Street and opened Captain Tony's Saloon.
Source: Old Town Manor, “Legends of Captain Tony's Saloon”; Captain Tony's Saloon history page
The State Library and Archives of Florida cataloged a circa-1969 photograph of Captain Tony's Saloon at 428 Greene Street.
Source: Florida Memory, “Capt. Tony's Saloon at 428 Greene St. in Key West,” circa 1969
Tarracino became mayor of Key West and served from 1989 to 1991.
Source: Florida Memory, “Captain Tony Tarracino in front of his saloon on Greene Street”
Captain Tony Tarracino died after continuing to appear at the saloon following his mayoral term.
Source: Old Town Manor, “Legends of Captain Tony's Saloon”
Captain Tony's became an informal Key West memorial site for former Mississippi State football coach Mike Leach, whose named stool had been displayed in the saloon.
Source: Palm Beach Post, “Mike Leach has barstool in his honor hanging at Capt. Tony's in Key West,” January 2, 2023
Florida Division of Corporations records and Monroe County property tax records confirm Joey Faber and Richard Johnson as Captain Tony's current owners. A separate ESPN feature's rendering of the owner's surname as "Felder" is a transcription error for Faber.
Source: Florida Division of Corporations (Sunbiz); Monroe County property tax records; verified directly by researcher Ed Donovan
Every claim gets rated. A business's own website can never earn "documented."
Captain Tony's occupies the Greene Street address where Joe Russell operated his 1930s bar before moving Sloppy Joe's to Duval Street. However, the Sun Sentinel reported conflicting accounts of the early bar's name, including The Blind Pig and The Silver Slipper, and Captain Tony's is a separate business opened in 1958.
The Sun Sentinel reported that Hemingway spent evenings at Joe Russell's Greene Street bar from 1933 to 1937. That supports the building's Hemingway association, but this research did not find a contemporaneous diary, photograph, bar ledger, or newspaper account documenting an individual visit.
Captain Tony's and local-history accounts say Buffett played the saloon in the early 1970s and was sometimes paid in tequila. Multiple later accounts repeat the connection, but this research did not locate a contemporary gig advertisement, newspaper review, photograph, or booking record that establishes dates or frequency.
ESPN reported that Leach sat at the saloon often enough that proprietors painted his name on a corner barstool. The Palm Beach Post reported that Captain Tony's displayed Leach's stool, memorial candle, and preferred drink after his December 2022 death, and described the bar as his favorite place for storytelling.
The ice-house-and-morgue account is repeated by the saloon, tourism businesses, and later lifestyle coverage. No municipal record, property record, contemporary newspaper item, or historical-society publication substantiating that combined use was located in this research.
The story is repeated in ghost-tour, tourism, and sports-feature coverage, with inconsistent totals. This research located no court record, sheriff's record, execution record, contemporary newspaper account, or municipal source documenting an execution at the address or supporting any claimed number of deaths.
Florida Division of Corporations records and Monroe County property tax records confirm both men as the saloon's current owners. Faber acquired the bar from Tarracino in 1988; press coverage has inconsistently rendered his surname, including once as "Felder," but the corporate and tax filings resolve his identity.
The claim appears in promotional and travel material, but no authoritative statewide comparison or documented continuous-operation record was found. Captain Tony's itself dates to 1958; the claimed nineteenth-century age belongs to the building and does not establish the age of the current saloon.
Everything below has been reported by two or more independent sources — this is an informational record of what's said about this place, not a verified account of paranormal activity. Still Open America doesn't certify hauntings as real.
Multiple accounts describe a woman in a blue or blood-stained blue dress, commonly called the Lady in Blue, as a recurring presence inside the saloon. Reports place blue specters or flashes of blue in the bar and identify the figure with the woman said to have been executed at the tree.
No court, sheriff, execution, or contemporary newspaper record was located to confirm the story that a woman was executed at 428 Greene Street after killing her husband and children.
The women's restroom is repeatedly described as a site of reported unexplained activity, including bathroom doors opening or closing by themselves, locks or doors behaving unexpectedly, and flashes of blue associated with the Lady in Blue legend.
Captain Tony's has operated continuously as the same bar since the building was constructed in 1851 or 1852.
Captain Tony's Saloon dates to 1958. Earlier businesses occupied the address, most notably Joe Russell's 1930s bar, but the building's history, Sloppy Joe's history, and Captain Tony's business history must be treated separately.
Source: Florida Memory, Captain Tony's Saloon collection; Sun Sentinel, July 21, 2004; Old Town Manor, “Legends of Captain Tony's Saloon”
Joe Russell moved Sloppy Joe's from Greene Street to Duval Street in 1938.
The date conflicts in available sources. The Sun Sentinel placed the move in 1937, while Captain Tony's own history gives 1938. The move is well supported; the exact year is not resolved here.
Source: Sun Sentinel, July 21, 2004; Captain Tony's Saloon history page
The tree inside Captain Tony's is a documented hanging tree where a known number of people died.
No primary execution or court record was located for a hanging at the address, and claimed totals vary. The hanging-tree account should be presented as unverified legend.
Source: No primary source found; ESPN, March 8, 2024, and ghost-tour and tourism accounts repeat inconsistent versions
The building's nineteenth-century age makes Captain Tony's Florida's oldest bar.
Captain Tony's opened in 1958. A building's age does not establish a current business's founding date or prove uninterrupted bar operation.
Source: Florida Memory, Captain Tony's Saloon collection; Old Town Manor, “Legends of Captain Tony's Saloon”
Captain Tony's has lasted by turning one Key West address into a living archive of stories: the former location of Joe Russell's 1930s bar, the home base of a flamboyant proprietor who became mayor, an early stage for Jimmy Buffett, and a gathering place for later regulars including football coach Mike Leach. Its continuity is layered rather than absolute. The building, the 1930s Sloppy Joe's operation, and Captain Tony's 1958 saloon are related histories, but they are not one uninterrupted business.
Captain Tony's Saloon opened under that name in 1958, according to Old Town Manor's history of the bar and the saloon's own history. Florida Memory independently confirms that Captain Tony's operated at 428 Greene Street by approximately 1969.
Captain Tony's occupies the Greene Street location where Joe Russell operated a bar before moving Sloppy Joe's to 201 Duval Street. The Sun Sentinel reported that the precise name history of the Greene Street business is disputed, and Captain Tony's itself is a separate saloon established in 1958.
Ernest Hemingway is associated with Joe Russell's 1930s Greene Street bar at the building now occupied by Captain Tony's, not with Captain Tony's itself, which opened in 1958. The Sun Sentinel reported that Hemingway spent evenings at the earlier bar from 1933 to 1937, but this research did not locate a contemporaneous account of a specific visit.
Captain Tony's and Old Town Manor say Jimmy Buffett played at the saloon in the early 1970s and later referenced Captain Tony Tarracino in his work. This research did not find a contemporary advertisement, review, or booking record that establishes a precise performance date.
Yes. ESPN reported in 2024 that Mike Leach sat at Captain Tony's often enough for proprietors to paint his name on a barstool, and the Palm Beach Post reported that the saloon honored him with his displayed stool after his death in December 2022.
The tree is widely described as a hanging tree, but the claimed number of executions varies among retellings. No identified court, sheriff, municipal, newspaper, or execution record was found in this research to verify that hangings occurred at the site.
Joey Faber and Richard Johnson currently own Captain Tony's Saloon, confirmed through Florida Division of Corporations records and Monroe County property tax records. Faber acquired the bar from Tony Tarracino in 1988. A 2024 ESPN feature rendered the owner's surname as "Felder," which is a transcription error for Faber.
428 Greene Street, Key West, FL 33040
(305) 294-1838
Visit for the saloon's living Key West culture and the Greene Street setting; interpret its signs, stools, and ghost lore as stories with varying levels of documentary support.