Born in a Prohibition bust (1929–1934)
Roxy’s traces its lineage to a speakeasy run by P.P. Dock at the corner of Okeechobee Road and South Dixie Highway; Dock had been in business at 401 Okeechobee Road since 1929 [3]. In 1933 — nine months before Prohibition was repealed — federal agents busted Dock on charges of “possession of intoxicating liquor” [3]. He pleaded guilty in October 1934, and two months later became one of the first two people to receive a liquor license issued by the City of West Palm Beach after Prohibition [3][4].
A note on the founding date: the bar’s own website says it was “established in 1933” [5], the Palm Beach Post’s photo retrospective dates the speakeasy to 1929 [6], and CBS12’s 2026 coverage calls it a 93-year-old establishment (implying 1933) [7]. The records are genuinely fuzzy here, as you’d expect for a business that began illegally.
Five owners, three locations (1934–2007)
In nearly a century, the bar has had five owners and three locations [3][4]. Dock ran it for several years before selling to Berlin Griffin, co-owner of the Palm Beach Kennel Club [3]. One of Griffin’s dog-track employees, Harry “Roxy” LaRocco, started working at the bar and bought it in 1949 — it became “Roxy’s” under him, and he ran it for about 25 years [3]. In 1974 it was purchased by Ken Wagner, a New Yorker who’d moved to the area for a restaurant-chain job [3].
The original building had its share of drama: in 1983, a police officer shot and killed a man at the bar after the man waved a gun at patrons [3]. In 1986 the building’s owner sold to developers Henry Rolfs and David Paladino, who razed it in 1989 as part of the failed Downtown/Uptown redevelopment project [3].
Roxy’s reopened in 1989 in the historic Comeau Building on Clematis Street — though the landlord initially insisted it be renamed the “Comeau Bar and Grill.” By the beginning of 1990, the awning said “Roxy’s” again [3]. The bar’s massive Brunswick bar — reportedly brought over from Palm Beach’s Whitehall Hotel in the 1920s — made the move too [3]. When Roxy’s arrived, Clematis was mostly deserted after dark; by 1993 the strip also included Respectable Street Café (opened 1987), Lost Weekend, Underground Coffeeworks, Narcissus and the Metropolis Club [3].
In 1997 Wagner bought a building two doors down and moved Roxy’s to its current home at 309 Clematis St. — he and his wife Pat strutted down the street to the new location with a bagpiper [3]. County property records confirm the purchase: Von Esselborn Inc. (more on that name shortly) took 309 Clematis by warranty deed in May 1997 for $630,000 [8].
Wagner, worn down by years of Clematis road construction, sold the business in 2005 [3].
The John P. Webb era (2007–present)
The buyer was John Webb, who reopened Roxy’s in early 2007 as an upscale Irish pub with a pool table, fireplace, and booths around the central bar [3]. Two years later he added Sky 309, a rooftop bar with a dance floor [3]. The bar became a Clematis institution: 1990s rock acts like Live and Candlebox played there, Snoop Dogg drew a crowd of 3,000 in 2010 [3], Mayor Lois Frankel celebrated her 2007 reelection there [3], and the annual St. Patrick’s Day party shuts down the whole 300 block [3][6].
In 2023, Webb pushed forward a $17 million expansion: a rooftop pool and restaurant — the first rooftop pool bar on Clematis — incorporating the vacant neighboring building at 313 Clematis, which he’d purchased in 2022 [4][9]. County records show Von Esselborn Inc. paid $7.5 million for 313 Clematis in October 2022 [10]. The city’s Downtown Action Committee approved two setback variances for the project [9], and the 300 block was closed to traffic for most of summer 2023 for crane work [11]. The rooftop venue, “Top of the Rox,” opened in July 2025 [12].