Standing eerily silent and in despair at the intersection of Jefferson and Ashley Streets, 644 West Ashley has seen better days. For those who don’t know anything about Jacksonville’s history, the 8,000-square foot building symbolizes the deteriorated condition of downtown and should have been demolished a long time ago. However, if we really knew our history, we would know that this place is something much more. It’s walls and its prominence at this former high profile LaVilla intersection are directly related to some of the most historically significant black musicians of the early 20th century.

Genovar’s Hall is identified as a saloon at the intersection of Ashley and Jefferson Streets in this 1913 Sanborn Map. Map courtesy of the Jacksonville Public Library Special Collections Department.

Originally built across the street from 19th-century madam Cora Crane’s Hotel de Dream, this three story structure housed a variety of businesses during the ragtime, jazz and blues age of the early 20th century. Pre-dating the Great Fire of 1901, 644 West Ashley Street was originally built in 1895, serving as a grocery market owned by Sebastian Genovar. During the first decades of the 20th century the building was occupied variety of businesses including a distillery, furniture store, shoe repair shop, restaurants and furnished rooms upstairs.

In 1931, the Wynn Hotel opened in the building’s upper floors. operated by Jack D. Wynn, the hotel became a favorite spot of Louis Armstrong when visiting Jacksonville. In town to perform at the nearby Knights of Pythias Hall, Armstrong preferred lodging at the Wynn because it was in the heart of LaVilla’s nightlife and entertainment scene. Wynn’s son, Daniel Ruben Wynn, is a noted local artist who had his work exhibited at the Center of International Culture in Paris, France in 1975. In later years, the Wynn Hotel was replaced by the Green Front Hotel.

For many decades, the first floor was occupied by the Lenape Tavern and Bar. Dating back to the early 1930s, the Lenape was one of the popular live performance venues on the Ashley Street strip. In addition to Armstrong, others who well known musicians associated with Lenape Tavern and Bar include Dizzie Gillespie, Billie Holiday, James Brown and Ray Charles, who briefly lived at 633 West Church Street.

The building’s fortunes declined with the neighborhood, as its economic foundation fell a part in the later half of the 20th century. Plans materialized in 1998 for the restoration of the historic structure. At the time, the Nu Beta Sigma Chapter of Phi Beta Sigma planned to invest $750,000 to convert the building into a museum and office space. Unfortunately after receiving $900,000 in public money, the project failed leaving the building in its current state.